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Journal articles on the topic 'Quinoline compounds'

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Published: 4 June 2021
Last updated: 1 February 2022

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1

Horta, Pedro, Marta S. C. Henriques, Elisa M. Brás, Fernanda Murtinheira, Fátima Nogueira, Paul M. O’Neill, José A. Paixão, Rui Fausto, and Maria L. S. Cristiano. "On the ordeal of quinolone preparation via cyclisation of aryl-enamines; synthesis and structure of ethyl 6-methyl-7-iodo-4-(3-iodo-4-methylphenoxy)-quinoline-3-carboxylate." Pure and Applied Chemistry 89, no. 6 (June 27, 2017): 765–80. http://dx.doi.org/10.1515/pac-2016-1119.

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AbstractRecent studies directed to the design of compounds targeting the bc1 protein complex of Plasmodium falciparum, the parasite responsible for most lethal cases of malaria, identified quinolones (4-oxo-quinolines) with low nanomolar inhibitory activity against both the enzyme and infected erythrocytes. The 4-oxo-quinoline 3-ester chemotype emerged as a possible source of potent bc1 inhibitors, prompting us to expand the library of available analogs for SAR studies and subsequent lead optimization. We now report the synthesis and structural characterization of unexpected ethyl 6-methyl-7-iodo-4-(3-iodo-4-methylphenoxy)-quinoline-3-carboxylate, a 4-aryloxy-quinoline 3-ester formed during attempted preparation of 6-methyl-7-iodo-4-oxo-quinoline-3-carboxylate (4-oxo-quinoline 3-ester). We propose that the 4-aryloxy-quinoline 3-ester derives from 6-methyl-7-iodo-4-hydroxy-quinoline-3-carboxylate (4-hydroxy-quinoline 3-ester), the enol form of 6-methyl-7-iodo-4-oxo-quinoline-3-carboxylate. Formation of the 4-aryloxy-quinoline 3-ester confirms the impact of quinolone/hydroxyquinoline tautomerism, both on the efficiency of synthetic routes to quinolones and on pharmacologic profiles. Tautomers exhibit different cLogP values and interact differently with the enzyme active site. A structural investigation of 6-methyl-7-iodo-4-oxo-quinoline-3-carboxylate and 6-methyl-7-iodo-4-hydroxy-quinoline-3-carboxylate, using matrix isolation coupled to FTIR spectroscopy and theoretical calculations, revealed that the lowest energy conformers of 6-methyl-7-iodo-4-hydroxy-quinoline-3-carboxylate, lower in energy than their most stable 4-oxo-quinoline tautomer by about 27 kJ mol−1, are solely present in the matrix, while the most stable 4-oxo-quinoline tautomer is solely present in the crystalline phase.
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2

Ghorab, Mostafa M., and Mansour S. Alsaid. "Anti-breast cancer activity of some novel quinoline derivatives." Acta Pharmaceutica 65, no. 3 (September 1, 2015): 271–83. http://dx.doi.org/10.1515/acph-2015-0030.

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Abstract To discover new bioactive lead compounds for medicinal purposes, 2-cyano-3-(4-substituted)-N-(quinolin-3-yl) acrylamide derivatives 2–24, chromenes 25, 26 and benzochromenes 27, 28 were synthesized. The structures of the newly synthesized compounds were confirmed by elemental analyses, IR, 1H NMR and 13C NMR spectroscopies. In addition, the structure of compound 1 was confirmed through X-ray crystallography. All the newly synthesized compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. The corresponding 2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(quinolin-3-yl) acrylamide (15), 3-oxo-N-(quinolin-3-yl)-3H-benzol[f] chromene-2-carboxamide (27), 2-cyano-3-(4-fluorophenyl-N-(quinolin-3-yl) acrylamide (7), 2-cyano-5-(4-(dimethyl-amino) phenyl)-N-(quinolin-3-yl) penta-2,4-dienamide (19) exhibited higher activity compared to doxorubicin (with IC50 value of 47.9 μmol L−1) as a reference drug, with IC50 values of 29.8, 39.0, 40.0, 40.4 μmol L−1, resp. Also, quinoline acrylamides containing 2,3,4-trimethoxyphenyl 17, 2-chlorophenyl 10, benzo[d][1,3]dioxol 12, 2-methoxynaphthalen 22, 2,4-dichlorophenyl 18 and quinoline carrying a chromene-3-carboxamide moiety 25 were nearly as active as doxorubicin, while quinoline acrylamides incorporating unsubstituted phenyl 2, p-tolyl 3, 2,4-dienamide 8, 3-nitrophenyl 13, 4-nitrophenyl 14, 3,4-dimethoxyphenyl 16 and chromene 26 exhibited a moderate activity. In addition, quinoline with acetamide 1, 4-hydroxyphenyl 4, 4-dimethylaminophenyl 9, 4-chlorophenyl 11, 3-bromophenyl 20, 4-bromophenyl 21 and 3-thienyl moiety 24 showed less activity than doxorubicin. On the other hand, quinoline having 2-methoxyphenyl 5, 4-methoxyphenyl 6, 4-metho xynaphthalene 23 and chromene-2-carboxamide 28 showed no activity.
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3

Xuan, Duc Dau. "Recent Progress in the Synthesis of Quinolines." Current Organic Synthesis 16, no. 5 (October 17, 2019): 671–708. http://dx.doi.org/10.2174/1570179416666190719112423.

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Background: Quinoline-containing compounds present in both natural and synthetic products are an important class of heterocyclic compounds. Many of the substituted quinolines have been used in various areas including medicine as drugs. Compounds with quinoline skeleton possess a wide range of bioactivities such as antimalarial, anti-bacterial, anthelmintic, anticonvulsant, antiviral, anti-inflammatory, and analgesic activity. Due to such a wide range of applicability, the synthesis of quinoline derivatives has attracted a lot of attention of chemists to develop effective methods. Many known methods have been expanded and improved. Furthermore, various new methods for quinoline synthesis have been established. This review will focus on considerable studies on the synthesis of quinolines date which back to 2014. Objective: In this review, we discussed recent achievements on the synthesis of quinoline compounds. Some classical methods have been modified and improved, while other new methods have been developed. A vast variety of catalysts were used for these transformations. In some studies, quinoline synthesis reaction mechanisms were also displayed. Conclusion: Many methods for the synthesis of substituted quinoline rings have been developed recently. Over the past five years, the majority of those reported have been based on cycloisomerization and cyclization processes. Undoubtedly, more imaginative approaches to quinoline synthesis will appear in the literature in the near future. The application of known methods to natural product synthesis is probably the next challenge in the field.
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4

Rogerio, Kamilla Rodrigues, Cedric Stephan Graebin, Luiza Helena Pinto Domingues, Luana Santos Oliveira, Vitoria de Souza Fernandes da Silva, Claudio Tadeu Daniel-Ribeiro, Leonardo J. M. Carvalho, and Nubia Boechat. "Novel Quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione Derivatives Against Chloroquine-resistant Plasmodium falciparum." Current Topics in Medicinal Chemistry 20, no. 2 (February 19, 2020): 99–110. http://dx.doi.org/10.2174/1568026619666191019100711.

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Introduction: In this work DHPMs were combined with the quinoline nucleus to obtain new quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione compounds with improved antiplasmodial activity as well as decreased cytotoxicity. Nineteen quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione derivatives connected by a linker group to quinolone ring moieties with different substituents were synthesized and assayed against P. falciparum. Materials and Methods: Nineteen quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione derivatives connected by a linker group to quinoline ring moieties with different substituents were synthesized and assayed against chloroquine-resistant Plasmodium falciparum, along with the reference drug chloroquine. Among these compounds, the derivatives with two methylene carbon spacers showed the best activity accompanied by low cytotoxicity. Results: The derivative without substituents on the aromatic ring (2a) and the derivative with a chlorine group at position 4 (2d) provided the best results, with IC50 = 1.15 µM and 1.5 µM, respectively. Conclusion: Compared to the parent drugs, these compounds presented marked decreases in cytotoxicity, with MDL50 values over 1,000 µM and selectivity indexes of >869.5 and >666.6, respectively. The quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione framework appears to be promising for further studies as an antimalarial for overcoming the burden of resistance in P. falciparum.
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5

Peerzade, Nargisbano A., Shravan Y. Jadhav, and Raghunath B. Bhosale. "Synthesis and Biological Evaluation of Some Novel Quinoline based Chalcones as Potent Antimalarial, Anti-inflammatory, Antioxidant and Antidiabetic Agents." Asian Journal of Chemistry 32, no. 4 (February 25, 2020): 959–64. http://dx.doi.org/10.14233/ajchem.2020.22542.

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The objective of the present study was to synthesize a series of some novel quinoline based methoxy substituted chalcones and to evaluate their in vitro antimalarial, anti-inflammatory, antioxidant and antidiabetic activitites. The quinoline based chalcones was synthesized by condensation of 2-chloro-3-formyl qunoline with various methoxy substituted acetophenone in presence of NaOH. The Claisen-Schmidt condensation gave high yield of quinoline based chalcones. Synthesis of 2-chloro-3-formyl quinoline was carried out by Vilsmeir-Haack reaction on acetanilide and 4-methoxy acetanilide which on cyclization along with formylation give corresponding 2-chloro-3-formyl quinoline. The synthesized compounds were screened for in vitro antimalarial, anti-inflammatory, antioxiadant and antidiabetic activities. The structures of the synthesized compounds were characterized by infrared, 1H NMR and 13C NMR spectroscopy. Compounds 1f and 1h showed highest antimalarial activity even more than standard chloroquine diphosphate. Compound 1a showed excellent activity whereas 1c and 1d showed potent anti-inflammatory activity as compared to standard diclofenac. On the other hand, compounds 1a and 1g showed excellent antioxidant activity for 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical while compound 1a showed highest inhibition of nitic oxide free radical (NO•) and compound 1h showed highest inhibition for super oxide radical (SOR) as well as highest antidiabetic activity as compared to standard acarbose. All quinolne based chalcones were synthesized in good yields and showed potential biological activities hence they may be helpful for the designing of new drugs.
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6

Faldu, V. J., P. K. Talpara, N. H. Bhuva, P. R. Vachharajani, and Viresh H. Shah. "Synthesis, Characterization and Biological Evaluation of some Newer 5-[6-Chloro/Fluor/Nitro-2-(p-Chloro/Fluoro/Methyl Phenyl)-Quinolin-4-yl]-1,3,4-Oxadiazole-2-Thiols." International Letters of Chemistry, Physics and Astronomy 25 (January 2014): 26–32. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.25.26.

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Recent study shows that quinolines represent one of the most active classes of compounds possesses wide spectrum biodynamic activities and use as potent therapeutic agents. In present research work, 5-[6-chloro/fluoro/nitro-2-(p-chloro/fluoro/methyl phenyl)-quinolin-4-yl]-1,3,4-oxadiazole-2-thiols have been synthesized by condensation of substituted quinoline-4-carbohydrazides and mixture of carbon disulphide and potassium hydroxide. All of these compounds were screened for their in vitro anti microbial assay against gram (+ve), gram (-ve) bacteria and fungi activity compared with standard drugs viz., Ampicilin, Chloramphenicol, Ciprofloxacin, Norfloxacin, Griseofulvin and Nystatin at different concentrations.
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7

Singhal, Anchal, Pratibha Kumari, and Kharu Nisa. "Facile One-Pot Friedlander Synthesis of Functionalized Quinolines using Graphene Oxide Carbocatalyst." Current Organic Synthesis 16, no. 1 (February 4, 2019): 154–59. http://dx.doi.org/10.2174/1570179415666181002114621.

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Background: Quinolines represent an important class of bioactive molecules which are present in various synthetic drugs, biologically active natural compounds and pharmaceuticals. Quinolines find their potential applications in various chemical and biomedical fields. Thereby, the demand for more efficient and simple methodologies for the synthesis of quinolines is growing rapidly. </P><P> Objective: The green one-pot Friedlander Synthesis of Functionalized Quinolines has been demonstrated by using graphene oxide as a carbocatalyst. </P><P> Method: The graphene oxide catalyzed condensation reaction of 2–aminoaryl carbonyl compounds with different cyclic/ acyclic/ aromatic carbonyl compounds in methanol at 70°C affords different quinoline derivatives. </P><P> Results: The reaction has been examined in different protic and aprotic solvents and the best yield of quinoline is observed in methanol at 70°C. Conclusion: The present method of quinoline synthesis offers various advantages over other reported methods such as short reaction time, high yield of product, recycling of catalyst and simple separation procedure. The graphene oxide carbocatalyst can be easily recovered from the reaction mixture by centrifugation and then can be reused several times without any significant loss in its activity.
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8

Upadhyay, Kuldip D., and Anamik K. Shah. "Evaluation of Pyrano[3,2 C] Quinoline Analogues as Anticancer Agents." Anti-Cancer Agents in Medicinal Chemistry 19, no. 10 (October 24, 2019): 1285–92. http://dx.doi.org/10.2174/1871520619666190308122734.

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Background: Quinoline analogues exhibited diversified biological activities depending on the structure type. A number of natural products with pyrano[3,2-c]quinolone structural motifs and patented chromenes were reported as promising cytotoxic agents. Objective: The present study is aimed to evaluate a new series of pyrano[3,2-c]quinoline scaffolds derived from the fusion of bioactive quinolone pharmacophore with structurally diverse aryl substituted chromene for its cytotoxicity. Methods: A library of pyrano[3,2-c]quinoline analogues was prepared from one-pot multi component synthesis using various aromatic aldehydes, malononitrile and 2,4-dihydroxy-1-methylquinoline. The new synthetics were primarily screened for its cytotoxicity (IC50) against different human cancer cell lines in vitro. The promising synthetics were further evaluated in vitro for their potency against different kinase activity. The promising compounds were finally tested for their in vivo efficacy in SCID type mice HCT-116 tumor model. Results: The screening results revealed that compounds 4c, 4f, 4i and 4j showed promising activity in in vitro study. However, compound 4c was found to be the most potent candidate with 23% tumor growth inhibition in HCT-116 tumor mice model. Conclusion: The structure activity relationship suggested that 3-substitution on the aryl ring at C4 position of the pyrano[3,2 c]quinolone moiety seems to have an important position for cytotoxicity activity. However, 3- chloro substitution at C4 aryl ring showed a significant alteration of the bioactive conformer of the parent scaffold and outcome with compound 4c as the most potent candidate of the series.
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9

Kumar, Praveen, Chinnappa Apattira Uthaiah, Santhosha Sangapurada Mahantheshappa, Nayak Devappa Satyanarayan, SubbaRao Venkata Madhunapantula, Hulikal Shivashankara Santhosh Kumar, and Rajeshwara Achur. "Antiproliferative potential, quantitative structure-activity relationship, cheminformatic and molecular docking analysis of quinoline and benzofuran derivatives." European Journal of Chemistry 11, no. 3 (September 30, 2020): 223–34. http://dx.doi.org/10.5155/eurjchem.11.3.223-234.2004.

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Quinoline and benzofuran moieties are commonly used for the synthesis of therapeutically beneficial molecules and drugs since they possess a wide range of pharmacological activities including potent anticancer activity as compared to other heterocyclic compounds. Many of well-known antimalarial, antimicrobial, anti-helminthic, analgesic, anti-inflammatory, antiprotozoal, and antitumor compounds contain quinoline/benzofuran skeleton. The aim of this study was to analyze ten new quinoline and eighteen benzofuran derivatives for carcinoma cell line growth inhibition and to predict possible interactions with the target. The anticancer activity of these compounds against colon cancer (HCT-116) and triple-negative breast cancer (MDA-MB-468) cell lines was determined and performed molecular docking to predict the possible interactions. Among ten quinoline derivatives, Q1, Q4, Q6, Q9, and Q10 were found to be the most potent against HCT-116 and MDA-MB-468 with IC50 values ranging from 6.2-99.6 and 2.7-23.6 μM, respectively. Using the IC50 values, a model equation with quantitative structure activity relationship (QSAR) was generated with their descriptors such as HBA1, HBA2, kappa (1, 2 and 3), Balaban index, Wiener index, number of rotatable bonds, log S, log P and total polar surface area (TPSA). The effect of benzofuran derivatives was moderate in cytotoxicity tests and hence only quinolines were considered for further analysis. The molecular docking indicated the mammalian / mechanistic target of rapamycin (mTOR), Topoisomerase I and II as possible targets for these molecules. The predicted results obtained from QSAR and molecular docking analysis of quinoline derivatives showed high correlation in comparison to the results of the cytotoxic assay. Overall, this study indicated that quinolines are more potent as anticancer agents compared to benzofurans. Further, compound Q9 has emerged as a lead molecule which could be the base for further development of more potent anticancer agents.
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10

Lin, Ying, Dong Xing, Wen-Biao Wu, Gao-Ya Xu, Li-Fang Yu, Jie Tang, Yu-Bo Zhou, Jia Li, and Fan Yang. "Design, Synthesis, and In Vitro Evaluation of Benzofuro[3,2-c]Quinoline Derivatives as Potential Antileukemia Agents." Molecules 25, no. 1 (January 3, 2020): 203. http://dx.doi.org/10.3390/molecules25010203.

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Herein, we design and synthesize an array of benzofuro[3,2-c]quinolines starting from 3-(2-methoxyphenyl)quinolin-4(1H)ones via a sequential chlorination/demethylation, intramolecular cyclization pathway. This sequential transformation was efficient, conducted under metal-free and mild reaction conditions, and yielded corresponding benzofuro[3,2-c]quinolines in high yields. In vitro biological evaluation indicated that such type of compounds showed excellent antileukemia activity and selectivity, and therefore may offer a promising hit compound for developing antileukemia compounds.
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11

Ambatkar, Megha P., and Pramod B. Khedekar. "Quinoline as TRPV1 Antagonists: A New Approach against Inflammation." Journal of Drug Delivery and Therapeutics 9, no. 4-s (August 25, 2019): 782–88. http://dx.doi.org/10.22270/jddt.v9i4-s.3414.

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Inflammation is the first response of the immune system to harmful stimuli such as infection or irritation, consists of a cascade of biochemical events that propagates and matures the inflammatory response. Number of anti-inflammatory drugs are available for treatment of acute and chronic inflammation. Many anti-inflammatory drugs cause adverse side effects. The quinoline class of compounds are important for searching the safe and effective anti-inflammatory drugs. These drugs are classified based on the number of substituents present on the quinoline ring or compounds containing a quinoline ring fused to other heterocyclic compounds. Quinolines have the ability to target several causes of inflammation includes transient receptor potential vanilloid 1 receptor. The TRPV1 receptor, first cloned and characterized in 1997, is a non-selective cation channel expressed in primary sensory neurons, and is a key pain sensor and integrator. This review provides the discovery of various quinoline derivatives as transient receptor potential vanilloid 1 (TRPV1) antagonists. Overall, the quinoline moiety will be used as a new template for designing and identifying the novel anti-inflammatory drugs in future. Keywords: Quinoline, Inflammation, Transient receptor Potential Vanilloid 1, Antagonists.
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12

Schmidt, Alexander, Matthias Baune, Alexander Hepp, Jutta Kösters, and Jens Müller. "Gold(III)-mediated cyclization of 2-hydrazinylquinolines." Zeitschrift für Naturforschung B 71, no. 5 (May 1, 2016): 527–33. http://dx.doi.org/10.1515/znb-2016-0021.

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AbstractThe Au(III)-mediated oxidative cyclization of a series of 2-hydrazinylquinolines is reported. This intramolecular reaction represents a reliable way towards obtaining various 3H-1,2,4-triazolo[4,3-a]quinolin-10-ium cations. The molecular structures of three of the starting compounds (2-(1-methyl-2-(pyridin-2-ylmethylene)hydrazinyl)quinoline, 2-(1-methyl-2-(thiophen-2-ylmethylene)hydrazinyl)quinoline, 2-((2-methyl-2-(quinolin-2-yl)hydrazono)methyl)aniline) as well as of one cyclized system (3-methyl-1-(pyridin-2-yl)-3H-1,2,4-triazolo[4,3-a]quinolin-10-ium dichloridoaurate(I)) were determined by means of single-crystal X-ray diffraction.
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13

Parekh, H. P., M. H. Chauhan, N. L. Solanki, and V. H. Shah. "A Clean, Benign, Energy Efficient One-Pot Multicomponent Synthesis and Bio-evaluation of Novel [1,2,4]Triazolo[1,5-a]quinolines." Asian Journal of Organic & Medicinal Chemistry 6, no. 2 (2021): 111–15. http://dx.doi.org/10.14233/ajomc.2021.ajomc-p322.

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In present work, a series of novel [1,2,4]triazolo[1,5-a]quinoline derivatives (HP-101-110) have been synthesized using multi-component reaction at room temperature in the presence of ammonium chloride as mild, cost effective green catalyst along with water as eco-friendly green solvent. The synthesis of 1,2,4-triazolo[1,5-a]quinolines (HP-101-110) was achieved by two step process. In first step, diversified Hantzsch pyridine reaction of an appropriate aromatic aldehyde, malononitrile, dimedone and benz hydrazide using ethanol as a solvent gives N-(2-amino-3-cyano-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8- tetrahydro-quinolin-1(4H)-yl)-4-hydroxybenzamide derivatives. In the second step, synthesis of the final product 2-(4-hydroxyphenyl)-8,8-dimethyl-6-oxo-5-phenyl-6,7,8,9-tetrahydro[1,2,4]triazolo[1,5- a]-quinoline-4-carbonitriles was achieved by the intramolecular cyclization of step 1 product.The structure of all the synthesized compounds (HP101-110) has been elucidated by FT-IR, 1H & 13C NMR, mass spectral data and elemental analyses.
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Tabassum, Rukhsana, Muhammad Ashfaq, and Hiroyuki Oku. "Recent Advances in Transition Metal Free Synthetic Protocols for Quinoline Derivatives." Current Organic Chemistry 24, no. 16 (November 9, 2020): 1815–52. http://dx.doi.org/10.2174/1385272824999200616122557.

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The quinoline moiety is a privileged scaffold among heterocyclic compounds that is an important construction motif in the fields of pharmaceutical chemistry. Quinoline molecule possesses a variety of therapeutic activities like antiviral, antimalarial, antibacterial, antitumor, anticancer, antioxidant antihypertensive, antifungal, anthelmintic, cardiotonic, anticonvulsant and anti-inflammatory. This review provides an insight into recent development in transition metal free novel and modified conventional synthetic routes to yield a wide variety of substituted quinolines.
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15

Mandal, Susanta, Samuzal Bhuyan, Saibal Jana, Jagir Hossain, Karan Chhetri, and Biswajit Gopal Roy. "Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinoline N-oxides." Green Chemistry 23, no. 14 (2021): 5049–55. http://dx.doi.org/10.1039/d1gc01460a.

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Quinolin-2(1H)-ones are prevalent in natural products and pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides.
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16

Torres Suarez, Elaine, Diana Susana Granados-Falla, Sara María Robledo, Javier Murillo, Yulieth Upegui, and Gabriela Delgado. "Antileishmanial activity of synthetic analogs of the naturally occurring quinolone alkaloid N-methyl-8-methoxyflindersin." PLOS ONE 15, no. 12 (December 28, 2020): e0243392. http://dx.doi.org/10.1371/journal.pone.0243392.

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Leishmaniasis is a neglected, parasitic tropical disease caused by an intracellular protozoan from the genus Leishmania. Quinoline alkaloids, secondary metabolites found in plants from the Rutaceae family, have antiparasitic activity against Leishmania sp. N-methyl-8-methoxyflindersin (1), isolated from the leaves of Raputia heptaphylla and also known as 7-methoxy-2,2-dimethyl-2H,5H,6H-pyran[3,2-c]quinolin-5-one, shows antiparasitic activity against Leishmania promastigotes and amastigotes. This study used in silico tools to identify synthetic quinoline alkaloids having structure similar to that of compound 1 and then tested these quinoline alkaloids for their in vitro antiparasitic activity against Leishmania (Viannia) panamensis, in vivo therapeutic response in hamsters suffering from experimental cutaneous leishmaniasis (CL), and ex vivo immunomodulatory potential in healthy donors’ human peripheral blood (monocyte)-derived macrophages (hMDMs). Compounds 1 (natural), 2 (synthetic), and 8 (synthetic) were effective against intracellular promastigotes (9.9, 3.4, and 1.6 μg/mL medial effective concentration [EC50], respectively) and amastigotes (5.07, 7.94, and 1.91 μg/mL EC50, respectively). Compound 1 increased nitric oxide production in infected hMDMs and triggered necrosis-related ultrastructural alterations in intracellular amastigotes, while compound 2 stimulated oxidative breakdown in hMDMs and caused ultrastructural alterations in the parasite 4 h posttreatment, and compound 8 failed to induce macrophage modulation but selectively induced apoptosis of infected hMDMs and alterations in the intracellular parasite ultrastructure. In addition, synthetic compounds 2 and 8 improved the health of hamsters suffering from experimental CL, without evidence of treatment-associated adverse toxic effects. Therefore, synthetic compounds 2 and 8 are potential therapeutic candidates for topical treatment of CL.
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S, Harishkumar, Satyanarayan Nd, and Santhosha Sm. "ANTIPROLIFERATIVE AND IN SILICO ADMET STUDY OF NEW 4-(PIPERIDIN-1-YLMETHYL)-2- (THIOPHEN-2-YL) QUINOLINE ANALOGUES." Asian Journal of Pharmaceutical and Clinical Research 11, no. 4 (April 1, 2018): 306. http://dx.doi.org/10.22159/ajpcr.2018.v11i4.24147.

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Objective: Synthesis and antiproliferative study of novel 4-(piperidin-1-ylmethyl)-2-(thiophen-2-yl) quinoline 7(a-j) derivatives.Methods: 4-(piperidin-1-ylmethyl)-2-(thiophen-2-yl) quinolines were synthesized by the addition of 4-(chloromethyl)-2-(thiophen-2-yl) quinoline (0.01 mol), piperidine (0.01 mol) in DMF (10 v) and K2CO3 (0.02 mol). The anticancer activity of the title compounds performed against T-47D, HeLa, HepG2, and MCF-7 human cancer cell lines growth was investigated by MTT assay.Results: The compounds 7b and 7g exhibited 90% of the growth inhibitory effect on T-47D, HeLa, and MCF-7 and also 80% growth inhibition in HepG2 when compared with standard drug paclitaxel.Conclusion: The synthesized compounds 4-(piperidin-1-ylmethyl)-2-(thiophen-2-yl) quinoline 7(a-j) exhibited a considerable degree of growth inhibition of human cancer cell lines. The synthesized molecules 7(a-j) are in acceptable range and are less toxic and can be considered as possible hits for drug discovery.
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18

Digafie, Zeleke, Yadessa Melaku, Zerihun Belay, and Rajalakshmanan Eswaramoorthy. "Synthesis, Molecular Docking Analysis, and Evaluation of Antibacterial and Antioxidant Properties of Stilbenes and Pinacol of Quinolines." Advances in Pharmacological and Pharmaceutical Sciences 2021 (March 2, 2021): 1–17. http://dx.doi.org/10.1155/2021/6635270.

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Emergence of antimicrobial resistance to standard commercial drugs has become a critical public health concern worldwide. Hence, novel antimicrobials with improved biological activities are urgently needed. In this regard, a series of quinoline-stilbene derivatives were synthesized from substituted quinoline and benzyltriphenylphosphonium chloride using Wittig reaction. Furthermore, a novel pinacol of quinoline was synthesized by pinacolinazation of 2-methoxyquinoline-3-carbaldehyde which was achieved by aluminum powder-potassium hydroxide reagent combination at ambient temperature in methanol. The structures of the synthesized compounds were established based on their spectral data. The antibacterial activities of the synthesized compounds were evaluated in vitro by the paper disc diffusion method against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram-negative bacteria (Escherichia coli and Salmonella typhimurium). The best activity was displayed by compound 19 against E. coli with an inhibition zone of 16.0 ± 0.82 mm and 14.67 ± 0.94 mm at 500 and 250 μg/mL, respectively. This is close to ciprofloxacin which is used as a positive control. The results of in silico molecular docking evaluation of the compounds against E. coli DNA gyraseB were in good agreement with the in vitro antibacterial analysis. Compounds 19 (−6.9 kcal/mol) and 24 (−7.1 kcal/mol) showed the maximum binding affinity close to ciprofloxacin (−7.3 kcal/mol) used as positive control. Therefore, the antibacterial activity displayed by these compounds is encouraging for further investigation to improve the activities of quinoline-stilbenes by incorporating various bioisosteric groups in one or more positions of the phenyl nuclei for their potential pharmacological use. Findings of the DPPH radical scavenging assay indicated that some of the quinolone stilbenes and pinacol possess moderate antioxidant properties compared to ascorbic acid used as a natural antioxidant.
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19

Gomes, Lígia R., Emerson T. da Silva, Marcus V. N. de Souza, James L. Wardell, and John N. Low. "Crystal structures, Hirshfeld surface analysis and Pixel energy calculations of three trifluoromethylquinoline derivatives: further analyses of fluorine close contacts in trifluoromethylated derivatives." Zeitschrift für Naturforschung B 74, no. 11-12 (December 18, 2019): 791–810. http://dx.doi.org/10.1515/znb-2019-0109.

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AbstractAs many studies have revealed, the introduction of a CF3 group into an organic compound can result in significant enhancement of biological activity. Factors which lead to this enhancement are thus of great interest. To investigate further this area, we have looked at the ability of fluorine to form close contacts with various atoms in organic compounds, e.g. F⋯F, F⋯O/O⋯F, F⋯C/C⋯F, H⋯F/F⋯H, and F⋯N/N⋯F, as indicated from crystal structure determinations and Hirshfeld analysis studies on trifluoromethylated compounds. Herein we first report the crystal structures, Hirshfeld surface analyses (HSA), and Pixel energy calculations of three trifluoromethylated quinoline derivatives, namely 2-(trifluoromethyl)quinolin-4-ol, 1, 4-ethoxy-2-(trifluoromethyl)quinoline, 2, and N1-(2,8-bis(trifluoromethyl)quinolin-4-yl)ethane-1,2-diamine, 3. Of particular interest is the determination of the various fluorine⋯atom close contacts. The total percentages of fluorine⋯atom close contacts in compounds 1–3 were determined to be high at 47, 41.2 and 60.7%, respectively. As relatively few HSA studies on trifluoromethylated compounds have reported the percentages of individual atom⋯atom close contacts, we have also determined the percentages of atom⋯atom close contacts for 20 more trifluoromethylated compounds: the range of total fluorine⋯atom close contacts for these compounds was 20–60%. While these data are based on connections between similar molecules in a crystalline state, they also clearly suggest that a compound containing CF3 group(s) has the potential to make extensive intermolecular connections/close contacts with organic material. Thus a possible factor for the enhanced biological activity of a compound bearing CF3 group(s) could be the propensity of the CF3 group to form many close contacts, thereby aiding binding or interaction with a biological target.
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20

Rádl, Stanislav, and Viktor Zikán. "Synthesis and biological activity of some basic-substituted 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinolines." Collection of Czechoslovak Chemical Communications 53, no. 8 (1988): 1812–19. http://dx.doi.org/10.1135/cccc19881812.

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Compounds Ia, Ib were obtained by an alkylation of 4,9-dihydro-6-hydroxy-1,3,9-trimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (VIIb) with the respective dialkylaminoalkyl chloride. The same alkylation of 4,9-dihydro-6-hydroxy-2,3,9-trimethyl-4-oxo-2H-pyrazolo[3,4-b]quinoline (VIIIb) yielded compounds IIa and IIb. Similar alkylation of 4,9-dihydro-6-hydroxy-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (IXa) and its 6-methoxy derivative (IXb) afforded IIIa-IIId. Compound IV was prepared from 4-chloro-3-methyl-1H-pyrazolo[3,4-b]quinoline (Xa) via its 1-(3-dimethylaminopropyl)derivative (Xb). Compounds VIa, VIb were prepared from 4,9-dihydro-6-hydroxy-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (IXc) and the respective dialkylaminoalkyl chloride. The compounds prepared were tested for antiviral activity in vivo in mice against influenza virus A2-Hongkong and encephalomyocarditis virus.
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21

Smetanin, N. V., and A. V. Mazepa. "Functionalization of N-arylmaleimides by sp3 C–H bonds of hydroacridines(qinolines)." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 6 (December 2020): 165–70. http://dx.doi.org/10.32434/0321-4095-2020-133-6-165-170.

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The catalyst-free sp3 C–H functionalization of tetrahydroacridine(quinolines) derivatives has been achieved using a Michael-type reaction with N-arylmaleimides. This method enables the facile synthesis of biologically important N-aryl bearing tetrahydroacridine(quinolines) moieties in a single step with high yields. The reaction occurs under non-catalytic conditions by heating of hydroacridines(quinolines) in DMSO within 4 h at 100–1200C. The reaction between starting compounds allows synthesizing (3S/4R)-3-[(3R/4S)-9-chloroacridine(quinoline)-4-yl]-1(-N-aryl)pyrrolidine-2,5-diones with a good yield. The structure of compounds was proved by spectral methods of analysis. The 1H NMR spectrum shows characteristic signals of protons of the CH-groups in acridine(quinoline) (3.4–3.5 ppm) and pyrrolidine (3.8–3.9 ppm) cycles. It is interesting to note that the main direction of the fragmentation is the Michael retro-reaction, which is accompanied by the elimination of 1-(2-nitrophenyl)-1H-pyrrole-2,5-dione and leads to the formation of m/z ions of starting chloroacridines(quinolines).
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22

Ramasamy, A. K., V. Balasubramaniam, and K. Mohan. "Synthesis and Characterization of Substituted 4-Methoxy-1H-quinolin-2-ones." E-Journal of Chemistry 7, no. 3 (2010): 1066–70. http://dx.doi.org/10.1155/2010/317391.

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An efficient method for the synthesis of various substituted 4-methoxy-1H-quinolin-2-ones from various substituted aniline with malonic acid, phosphorous oxychloride, sodium methoxide and glacial acetic acid under different conditions is described. The title compounds were synthesized from three steps; the first step involved the synthesis of substituted 2, 4-dichloro quinoline from aniline (substituted), with malonic acid and phosphorous-oxychloride. In the second step, the substituted 2, 4 dichloro compounds was heated with freshly prepared methanolic sodium methoxide solution to give 2, 4-dimethoxy quinoline compounds, it was then refluxed with glacial acetic acid and hydrochloric acid to give the titled compounds in the final step. The purity of the synthesized compounds was confirmed by their C, H and N analysis and the structure was analyzed on the basics of Mass, FT-IR and1H NMR.
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23

Suman, Kancharla, Jyothi Prashanth, Koya Prabhakara Rao, Madala Subramanyam, Vejendla Anuradha, and Mandava Venkata Basaveswara Rao. "Facile Synthesis of 6-Phenyl-6h-chromeno [4, 3-b] Quinoline Derivatives using NaHSO4@SiO2 Re-usable Catalyst and Their Antibacterial Activity Study Correlated by Molecular Docking Studies." Letters in Drug Design & Discovery 17, no. 7 (July 6, 2020): 929–38. http://dx.doi.org/10.2174/1570180816666190731115809.

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Background: Heterocyclic compounds containing heteroatoms (O, N and S) as part of five or six-membered cyclic moieties exhibited various potential applications, such as pharmaceutical drugs, agrochemical products and organic materials. Among many known heterocyclic moieties, quinoline and its derivatives are one of the privileged scaffolds found in many natural products. In general, quinoline derivatives could be prepared by utilizing ortho-substituted anilines and carbonyl compounds containing a reactive α-methylene group of well-known reaction routes like Friedlander synthesis, Niemantowski synthesis and Pfitzinger synthesis. Moreover, polysubstituted quinolones and their derivatives also had shown considerable interest in the fields of organic and pharmaceutical chemistry in recent years. Objective: The main objective of our research work is towards the design and synthesis of divergent biological-oriented, proactive analogues with potential pharmacological value inspired by the anti-tubercular activity of 2-phenylquinoline analogues. In this study, we have been interested in the design and synthesis of bioactive, 2, 4-diphenyl, 8-arylated quinoline analogues. Methods: 6-phenyl-6h-chromeno [4, 3-b] quinoline derivatives were synthesized from 4-chloro-2- phenyl-2H-chromene-3-carbaldehyde and various substituted aromatic anilines as starting materials using sodium bisulfate embedded SiO2 re-usable catalyst. All these fifteen new compound structures confirmed by spectral data 1H & 13C NMR, Mass, CHN analysis etc. Furthermore, all these new compounds antibacterial activity strains recorded using the paper disc method. The compound molecular structures were designed using molecular docking study by utilizing the crystallographic parameters of S. Areus Murb protein. Results: A series of fifteen new quinoline derivatives synthesized in moderate to good yields using sodium bisulfate embedded SiO2 re-usable catalyst. The molecular structures of these newly synthesized compounds elucidated by the combination of spectral data along with the elemental analysis. These compounds antibacterial activity study have shown moderate to good activity against, Escherichia coli (Gram-negative) and Staphylococcus aureus (gram-positive) organisms. These antibacterial activity results were also a very good correlation with molecular docking studies. Conclusion: In this study, fifteen new quinoline derivatives synthesized and structures confirmed by spectral data. In fact, all the compounds have shown moderate to good antibacterial activity. In general, the compounds containing the electron donor group at R1 position (R1 = OMe) and the acceptor group at R2 positions (R2 = F or Cl) had shown good antibacterial activity. These antibacterial activity results were also a very good correlation with molecular docking studies showing strong binding energies with the highest value being, -12.45 Kcal mol-1 with S. aureus MurB receptor.
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24

Yurttaş, Leyla, and Gülşen A. Çiftçi. "New Quinoline Based Sulfonamide Derivatives: Cytotoxic and Apoptotic Activity Evaluation Against Pancreatic Cancer Cells." Anti-Cancer Agents in Medicinal Chemistry 18, no. 8 (December 28, 2018): 1122–30. http://dx.doi.org/10.2174/1871520618666180307142629.

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Background: Quinoline is a privileged scaffold especially known with antimalarial and antibacterial drugs before, presently followed anticancer efficiency with a new group of protein kinase inhibitors. Objective: In this work, combining quinoline ring, hydrazone and sulphonamide groups, we have synthesized N'-arylidene-2-[4-(quinolin-8-ylsulfonyl)piperazin-1-yl]acetohydrazide derivatives (3a-o) and evaluated their in vitro anticancer activity against cancerous cell lines PANC-1, CAPAN-1, and healthy cell line hTERT-HPNE. Method: Fifteen compounds were synthesized a simple, well-known three-step synthetic procedure starting from 8-quinolinesulfonylchloride. Cytotoxicity studies were performed according to the conventional MTT method. As a second stage, flow cytometric analysis was done to the nine most cytotoxic compounds for determining the mechanism of action which could be apoptosis and/or necrosis. </P><P> Results/Conclusion: According to anticancer activity evaluation, compound 3b bearing 4-methyl phenyl moiety exhibited significant cytotoxicity which has an IC50 value nearly four-fold lower than cisplatin displayed, whereas compound 3f bearing 4-trifluoromethyl phenyl moiety showed two-fold potency of the standard drug against PANC-1 cell line. Compounds 3h, 3k and 3n against CAPAN-1 also showed significant cytotoxicity, selectively. The most active compounds 3b, 3c, 3d, 3f, 3g, 3h, 3k and 3n against PANC-1 and compounds 3f, 3g, 3h, 3k and 3n against CAPAN-1 were selected to be studied in flow cytometry. Compound 3b induced apoptosis of PANC-1 cells with a percentage of 16.0%, whereas compound 3h induced apoptosis of CAPAN-1 cells with a value of 20.6%.
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25

Battista, Sara, Vincenzo Marsicano, Antonio Arcadi, Luciano Galantini, Massimiliano Aschi, Elena Allegritti, Alessandra Del Giudice, and Luisa Giansanti. "UV Properties and Loading into Liposomes of Quinoline Derivatives." Colloids and Interfaces 5, no. 2 (May 7, 2021): 28. http://dx.doi.org/10.3390/colloids5020028.

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The scientific relevance of quinolines is strictly linked to the fine-tuning of their features by functionalizing the heterocyclic core. Consequently, the compounds of this class are very versatile and can be used as possible drugs for a lot of medical applications. In this work, the inclusion of eight synthetic quinoline derivatives in liposomes formulated with different lipids was investigated in terms of the encapsulation efficiency and to highlight the effect on the liposome size distribution and thermotropic behavior. Excellent encapsulation was accomplished with all the quinoline/phospholipid combinations. Differences in the interactions at the molecular level, dependent on the quinoline molecular scaffolds and lipid structure, were observed, which could significantly bias the interaction with the drug and its release in pharmaceutical applications. Experiments in combination with computational studies demonstrated that the UV absorption of quinolines with expanded conjugation could be affected by the environment polarity. This was probably due to a solvent-dependent ability of these quinolines to stack into aggregates, which could also occur upon inclusion into the lipid bilayer.
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26

Nasseri, Mohammad Ali, Batol Zakerinasab, and Sayyede Kamayestani. "Proficient Procedure for Preparation of Quinoline Derivatives Catalyzed by NbCl5 in Glycerol as Green Solvent." Journal of Applied Chemistry 2015 (January 21, 2015): 1–7. http://dx.doi.org/10.1155/2015/743094.

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Quinolines, an important class of potentially bioactive compounds, have been synthesized by treatment of o-aminoaryl ketones and carbonyl compound utilizing niobium (V) chloride (NbCl5) as an available and inexpensive catalyst. The quinoline derivatives were prepared in glycerol, an excellent solvent in terms of environmental impact, with high yields (76–98%) and short reaction times (20–90 min). Not only diketones but also ketones afforded the desired products in good to excellent yields. The reaction time of 2-amino-5-chlorobenzophenone and dicarbonyl compounds was longer than that of 2-aminobenzophenone. The reaction of cyclic diketones took place faster than open chain analogues. These reactions also proceeded with acetophenone derivatives. In these cases the reaction times are longer.
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27

Abd El-Aal, Hassan A. K., and Talaat I. El-Emary. "Synthesis of Tetracyclic Fused Quinolines via a Friedel–Crafts and Beckmann Ring Expansion Sequence." Australian Journal of Chemistry 72, no. 12 (2019): 945. http://dx.doi.org/10.1071/ch19363.

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An efficient protocol for the construction of tetracyclic fused quinolines (pyrazole-fused azepino-, azocino-, and azonino[3,2-b]quinolinones) via consecutive Friedel–Crafts and Beckmann reactions has been developed. The key steps in the syntheses of these new molecular scaffolds involve acid-mediated cyclization of 2-(pyrazol-3-yl)quinoline based carboxylic acids 6a–c, 8, and 12 to ketones 13a–e, followed by Beckmann rearrangements of the corresponding oximes 14a–e to provide the tetracyclic-fused quinoline skeletons 15a–e. Structures of synthesised compounds without stereochemical implication were confirmed by NMR and elemental analyses.
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28

Abd El-Aal, Hassan A. K., and Talaat I. El-Emary. "Corrigendum to: Synthesis of Tetracyclic Fused Quinolines via a Friedel–Crafts and Beckmann Ring Expansion Sequence." Australian Journal of Chemistry 72, no. 12 (2019): 990. http://dx.doi.org/10.1071/ch19363_co.

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An efficient protocol for the construction of tetracyclic fused quinolines (pyrazole-fused azepino-, azocino-, and azonino[3,2-b]quinolinones) via consecutive Friedel–Crafts and Beckmann reactions has been developed. The key steps in the syntheses of these new molecular scaffolds involve acid-mediated cyclization of 2-(pyrazol-3-yl)quinoline based carboxylic acids 6a–c, 8, and 12 to ketones 13a–e, followed by Beckmann rearrangements of the corresponding oximes 14a–e to provide the tetracyclic-fused quinoline skeletons 15a–e. Structures of synthesised compounds without stereochemical implication were confirmed by NMR and elemental analyses.
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29

Kwak, Sang Woo, Ju Hyun Hong, Sang Hoon Lee, Min Kim, Yongseog Chung, Kang Mun Lee, Youngjo Kim, and Myung Hwan Park. "Synthesis and Photophysical Properties of a Series of Dimeric Indium Quinolinates." Molecules 26, no. 1 (December 23, 2020): 34. http://dx.doi.org/10.3390/molecules26010034.

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A novel class of quinolinol-based dimeric indium complexes (1–6) was synthesized and characterized using 1H and 13C(1H) NMR spectroscopy and elemental analysis. Compounds 1–6 exhibited typical low-energy absorption bands assignable to quinolinol-centered π–π* charge transfer (CT) transition. The emission spectra of 1–6 exhibited slight bathochromic shifts with increasing solvent polarity (p-xylene < tetrahydrofuran (THF) < dichloromethane (DCM)). The emission bands also showed a gradual redshift, with an increase in the electron-donating effect of substituents at the C5 position of the quinoline groups. The absolute emission quantum yields (ΦPL) of compounds 1 (11.2% in THF and 17.2% in film) and 4 (17.8% in THF and 36.2% in film) with methyl substituents at the C5 position of the quinoline moieties were higher than those of the indium complexes with other substituents.
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30

Heleyová, Katarína, and Dušan Ilavský. "Gould-Jacobs Reaction of 5- and 6-Amino-2-substitutedBenzoxazoles. III. Reaction with 3-Ethoxy-2-cyanopropenonitrile and Ethyl 3-Ethoxy-2-cyanopropenoate." Collection of Czechoslovak Chemical Communications 62, no. 1 (1997): 99–108. http://dx.doi.org/10.1135/cccc19970099.

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Nucleophilic reaction of 5-amino- (1) and 6-amino-2-substituted benzoxazoles (2) with 3-ethoxy-2-cyanopropenonitrile (3) afforded the respective benzoxazolylaminomethylenemalononitriles 5 and 6. The amino derivatives 1 and 2 reacted with ethyl 3-ethoxy-2-cyanopropenoate (4) to give the corresponding esters of benzoxazolylamino-2-cyanopropenoic acid 7 and 8, respectively. The products 7 on thermal cyclization at 250-260 °C in a mixture of diphenyl ether and biphenyl afforded a mixture of angularly and linearly annelated 5-nitrile-4-oxooxazolo[4,5-f]quinoline 9 and 7-nitrile-8-oxooxazolo[5,4-g]quinoline 10; under the same conditions compounds 8 were converted into 8-nitrile-9-oxooxazolo[5,4-f]quinolines 11 and 6-nitrile-5-oxooxazolo[4,5-g]quinolines 12.
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31

V, Sangeetha. "SYNTHESIS OF ISOXAZOLO AND PYRAZOLINO ANNELATED CARBAZOLES FROM 2-(3'-(2'-CHLORO) QUINOLIDINE)-1-OXO-1, 2, 3, 4-TETRAHYDROCARBAZOLE AND 2-CHLORO-3-FORMYLQUINOLINE." Kongunadu Research Journal 2, no. 1 (June 30, 2015): 29–31. http://dx.doi.org/10.26524/krj61.

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1-Oxo-1,2,3,4-tetrahydrocarbazole (1) on mixed aldol condensation with 2-chloro-3-formylquinoline (2) ielded 2-(3'-(2'-chloro)quinolidine)-1-oxo-1,2,3,4-tetrahydrocarbazole (3), which was further treated with hydroxylamine hydrochloride and hydrazine hydrate in separate reactions to afford 4,5-dihydro-3-3'-(2'-chloro) quinoline -isoxazolo [3,4-a]carbazole (4) and 3'-(2'-chloro)- quinoline- 3,3a,4,5- tetrahydro- 2Hpyrazolino [3,4-a]carbazole (5). The prepared compounds were elaluated for their invitro antibacterial and antifungal activities against certain pathogenic fungal and bacterial strains.
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32

Ma, Xiangjuan, Lixia Bian, Jingfeng Ding, Yaping Wu, Huilong Xia, and Jionghui Li. "Electrochemical oxidation of quinoline aqueous solution on β-PbO2 anode and the evolution of phytotoxicity on duckweed." Water Science and Technology 75, no. 8 (January 31, 2017): 1820–29. http://dx.doi.org/10.2166/wst.2017.053.

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Electrochemical oxidation of quinoline on a β-PbO2 electrode modified with fluoride resin and the comprehensive toxicity of intermediates formed during oxidation on duckweed were investigated in detail. The results showed that quinoline was initially hydroxylated at the C-2 and C-8 positions by hydroxyl radicals (·OH) electro-generated on a β-PbO2 anode, yielding 2(1H)-quinolinone and 8-hydroxyquinoline, then undergoing ring cleavage to form pyridine, nicotinic acid, pyridine-2-carboxaldehyde and acetophenone, which were ultimately converted to biodegradable organic acids. NO3− was the final form of quinoline-N. The growth of duckweed exposed to the oxidized quinoline solution was gradually inhibited with the decrease in pH and the formation of intermediates. However, the growth inhibition of duckweed could be eliminated beyond 120 min of oxidation, indicating the comprehensive toxicity of the quinoline solution reduced when the amount of quinoline removed was above 80%. Additionally, the adjustment of the pH to 7.5 and the addition of nutrients to the treated quinoline solution before culturing duckweed could obviously alleviate the inhibition on duckweed. Thus, partial electrochemical degradation of quinoline offers a cost-effective and clean alternative for pretreatment of wastewater containing nitrogen-heterocyclic compounds before biological treatment. The duckweed test presents a simple method for assessing the comprehensive toxicity of intermediates.
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33

Marepu, Nagaraju, Mahesh Gosi, Santhoshi Sumana Vedula, Sunandamma Yeturu, and Manojit Pal. "Ultrasound-assisted Synthesis of 6-substituted indolo[2,3-b]quinolines: their Evaluation as Potential Cytotoxic Agents." Mini-Reviews in Medicinal Chemistry 19, no. 7 (March 28, 2019): 599–608. http://dx.doi.org/10.2174/1389557518666180727170055.

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<p>Background: The indolo[2,3-b]quinoline framework is often found in various natural products displaying a range of pharmacological activities. This is an attractive template for the design and discovery of potential drugs especially for the identification of new anticancer agents. Methods: The synthesis of 6-substituted indolo[2,3-b]quinolones was undertaken and carried out using a ultrasound assisted method involving two sequential C-N bond forming reactions between 3-(2- bromophenyl)-2-chloroquinoline and amines in a single pot in the presence of Pd(OAc)2 and a ligand (S)-BINAP. All the synthesized compounds were tested in vitro against two cancer cell lines e.g. MCF7 and HepG2 along with non-cancerous HEK293 cell lines. Results: Two of these compounds showed promising and selective growth inhibition of MCF7 cell lines and one induced significant apoptosis in cancer (MCF7) cells. Conclusion: Compounds based on indolo[2,3-b]quinolone framework may be useful for the identification of new cytotoxic agents thereby potential cure for breast cancer.</p>
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34

Guan, Yong-Feng, Xiu-Juan Liu, Xin-Ying Yuan, Wen-Bo Liu, Yin-Ru Li, Guang-Xi Yu, Xin-Yi Tian, et al. "Design, Synthesis, and Anticancer Activity Studies of Novel Quinoline-Chalcone Derivatives." Molecules 26, no. 16 (August 13, 2021): 4899. http://dx.doi.org/10.3390/molecules26164899.

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The chalcone and quinoline scaffolds are frequently utilized to design novel anticancer agents. As the continuation of our work on effective anticancer agents, we assumed that linking chalcone fragment to the quinoline scaffold through the principle of molecular hybridization strategy could produce novel compounds with potential anticancer activity. Therefore, quinoline-chalcone derivatives were designed and synthesized, and we explored their antiproliferative activity against MGC-803, HCT-116, and MCF-7 cells. Among these compounds, compound 12e exhibited a most excellent inhibitory potency against MGC-803, HCT-116, and MCF-7 cells with IC50 values of 1.38, 5.34, and 5.21 µM, respectively. The structure–activity relationship of quinoline-chalcone derivatives was preliminarily explored in this report. Further mechanism studies suggested that compound 12e inhibited MGC-803 cells in a dose-dependent manner and the cell colony formation activity of MGC-803 cells, arrested MGC-803 cells at the G2/M phase and significantly upregulated the levels of apoptosis-related proteins (Caspase3/9 and cleaved-PARP) in MGC-803 cells. In addition, compound 12e could significantly induce ROS generation, and was dependent on ROS production to exert inhibitory effects on gastric cancer cells. Taken together, all the results suggested that directly linking chalcone fragment to the quinoline scaffold could produce novel anticancer molecules, and compound 12e might be a valuable lead compound for the development of anticancer agents.
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35

Mehta, Jugal V., Sanjay B. Gajera, Dilip B. Raval, Vasudev R. Thakkar, and Mohan N. Patel. "Biological assessment of substituted quinoline based heteroleptic organometallic compounds." MedChemComm 7, no. 8 (2016): 1617–27. http://dx.doi.org/10.1039/c6md00251j.

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Spectral changes accompanying addition of HS DNA to solution of quinoline nucleus based piano stool coordination compounds indicate intercalative mode of binding of the compound between DNA base pairs.
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36

Erguc, Ali, Mehlika Dilek Altintop, Ozlem Atli, Belgin Sever, Gokalp Iscan, Gozde Gormus, and Ahmet Ozdemir. "Synthesis and Biological Evaluation of New Quinoline-Based Thiazolyl Hydrazone Derivatives as Potent Antifungal and Anticancer Agents." Letters in Drug Design & Discovery 15, no. 2 (January 30, 2018): 193–202. http://dx.doi.org/10.2174/1570180814666171003145227.

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Background: In medicinal chemistry, thiazoles have gained great importance in antifungal and anticancer drug design and development. Objectives: The aim of this study was to synthesize new quinoline-based thiazolyl hydrazone derivatives and evaluate their anticandidal and anticancer effects. Methods: New thiazolyl hydrazone derivatives were evaluated for their anticandidal effects using disc diffusion method. Ames MPF assay was carried out to determine the genotoxicity of the most effective antifungal derivative. MTT assay was also performed to assess the cytotoxic effects of the compounds on A549 human lung adenocarcinoma, HepG2 human hepatocellular carcinoma, MCF- 7 human breast adenocarcinoma and NIH/3T3 mouse embryonic fibroblast (healthy) cell lines. Methods: Results: 4-(4-Fluorophenyl)-2-(2-((quinolin-4-yl)methylene)hydrazinyl)thiazole (4) showed antifungal activity against Candida albicans and Candida krusei in the concentration of 1 mg/mL. In MTT and Ames MPF tests, it was determined that compound 4 did not show cytotoxic and genotoxic effects. MTT assay indicated that 4-(naphthalen-2-yl)-2-(2-((quinolin-4-yl)methylene) hydrazinyl)thiazole (10) showed more selective anticancer activity than cisplatin against A549 and MCF-7 cell lines. Besides, 4-(4-chlorophenyl)-2-(2-((quinolin-4-yl)methylene)hydrazinyl)thiazole (5) exhibited more selective anticancer activity than cisplatin against HepG2 cell line. Conclusion: Due to their high selectivity index, these compounds are considered as candidate compounds to participate in further research.
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37

Fu, Hai-Gen, Zhi-Wen Li, Xin-Xin Hu, Shu-Yi Si, Xue-Fu You, Sheng Tang, Yan-Xiang Wang, and Dan-Qing Song. "Synthesis and Biological Evaluation of Quinoline Derivatives as a Novel Class of Broad-Spectrum Antibacterial Agents." Molecules 24, no. 3 (February 2, 2019): 548. http://dx.doi.org/10.3390/molecules24030548.

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Nineteen new quinoline derivatives were prepared via the Mannich reaction and evaluated for their antibacterial activities against both Gram-positive (G+) and Gram-negative (G−) bacteria, taking compound 1 as the lead. Among the target compounds, quinolone coupled hybrid 5d exerted the potential effect against most of the tested G+ and G− strains with MIC values of 0.125–8 μg/mL, much better than those of 1. Molecular-docking assay showed that compound 5d might target both bacterial LptA and Top IV proteins, thereby displaying a broad-spectrum antibacterial effect. This hybridization strategy was an efficient way to promote the antibacterial activity of this kind, and compound 5d was selected for the further investigation, with an advantage of a dual-target mechanism of action.
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38

Sultana, Rizuana, and Ravinder Reddy Tippanna. "A Novel and Different Approach for the Synthesis of Quinoline Derivatives Starting Directly from Nitroarenes and Their Evaluation as Anti-Cancer Agents." International Journal of Chemistry 12, no. 1 (February 13, 2020): 99. http://dx.doi.org/10.5539/ijc.v12n1p99.

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A series of new quinoline derivatives (6-phenyl-6H-chromeno, [4,3-b] quinoline) have been prepared by using 4-chloro-2-phenyl-2H-chromene-3-carbaldehyde and various substituted nitroarenes as starting materials in the presence of Tin (II) chloride dihydrate and ethanol. The conversion in this synthesis involves the following steps (i) reduction of nitroarenes to anilines, (ii) Coupling of the anilines, chromene aldehydes (iii) Cyclization of resulting species and (iv) dehydration of cyclic intermediates. Several new quinolones have been prepared. We screened eight compounds of this novel series (6a-r) in three different cancer cell lines (B16F10, MCF7 and A549). The screened compounds showed moderate anticancer activity on two of the studied cell lines with best IC50 values of compound 6i (6.10&plusmn;1.23 &micro;M) and 6m (8.21&plusmn;2.31 &micro;M) on MCF7 cells. The selected compounds 6i and 6m led to morphological changes after treatment on MCF7 cell line. Interestingly, detailed studies suggested that the compounds 6i and 6m induced apoptosis in MCF7 cells in an oxidative stress independent manner without causing necrosis. In addition, we found destabilization of mitochondrial membrane potential behind the observed anticancer activity. Our results clearly indicate the promising anticancer potential of this novel series. This method is operationally simple and works with a diverse range of substrates.
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39

Vandekerckhove, Stéphanie, and Matthias D’hooghe. "Quinoline-based antimalarial hybrid compounds." Bioorganic & Medicinal Chemistry 23, no. 16 (August 2015): 5098–119. http://dx.doi.org/10.1016/j.bmc.2014.12.018.

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40

Milićević, David, Roman Kimmel, Martin Gazvoda, Damijana Urankar, Stanislav Kafka, and Janez Košmrlj. "Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones." Molecules 23, no. 9 (September 10, 2018): 2310. http://dx.doi.org/10.3390/molecules23092310.

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Derivatives of 3-(1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione unsubstituted on quinolone nitrogen atom, which are available by the previously described four step synthesis starting from aniline, were exploited as intermediates in obtaining the title compounds. The procedure involves the introduction of propargyl group onto the quinolone nitrogen atom of mentioned intermediates by the reaction of them with propargyl bromide in N,N-dimethylformamide (DMF) in presence of a potassium carbonate and the subsequent formation of a second triazole ring by copper catalyzed cyclisation reaction with azido compounds. The products were characterized by 1H, 13C and 15N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (1H–1H gs-COSY, 1H–13C gs-HSQC, 1H–13C gs-HMBC) with 1H–15N gs-HMBC as a practical tool to determine 15N NMR chemical shifts at the natural abundance level of 15N isotope.
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41

Nakayama, Hector, Philippe M. Loiseau, Christian Bories, Susana Torres de Ortiz, Alicia Schinini, Elsa Serna, Antonieta Rojas de Arias, et al. "Efficacy of Orally Administered 2-Substituted Quinolines in Experimental Murine Cutaneous and Visceral Leishmaniases." Antimicrobial Agents and Chemotherapy 49, no. 12 (December 2005): 4950–56. http://dx.doi.org/10.1128/aac.49.12.4950-4956.2005.

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ABSTRACT We report in this study the in vivo efficacy of nine 2-substituted quinolines on the Leishmania amazonensis cutaneous infection murine model and on the Leishmania infantum and Leishmania donovani visceral infection murine models. In the case of the L. amazonensis model, quinolines were administered orally at 25 mg/kg twice daily for 15 days. Quinolines 1, 2, 3, and 7 reduced by 80 to 90% the parasite burdens in the lesion, whereas N-methylglucamine antimoniate (Glucantime), administered by subcutaneous injections at 100 mg [28 mg Sb(V)] per kg of body weight daily, reduced the parasite burdens by 98%. In visceral leishmaniasis due to L. infantum, mice treated orally at 25 mg/kg daily for 10 days with quinolines 1, 4, 5, and 6 showed a significant reduction of parasite burdens in the liver and spleen. These quinolines were significantly more effective than meglumine antimoniate to reduce the parasite burden in both the liver and spleen. Also, the oral in vivo activity of three quinolines (quinolines 4, 5, and 2-n-propylquinoline) were determined against L. donovani (LV 9) at 12.5 and 25 mg/kg for 10 days. Their activity was compared with that of miltefosine at 7.5 mg/kg. Miltefosine, 2-n-propylquinoline, and quinoline 5 at 12.5 mg/kg significantly reduced the parasite burdens in the liver by 72, 66, and 61%, respectively. From the present study, quinoline 5 is the most promising compound against both cutaneous and visceral leishmaniasis. The double antileishmanial and antiviral activities of these compounds suggest that this series could be a potential treatment for coinfection of Leishmania-human immunodeficiency virus.
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Tempone, André Gustavo, Ana Cláudia Melo Pompeu da Silva, Carlos Alberto Brandt, Fernanda Scalzaretto Martinez, Samanta Etel Treiger Borborema, Maria Amélia Barata da Silveira, and Heitor Franco de Andrade. "Synthesis and Antileishmanial Activities of Novel 3-Substituted Quinolines." Antimicrobial Agents and Chemotherapy 49, no. 3 (March 2005): 1076–80. http://dx.doi.org/10.1128/aac.49.3.1076-1080.2005.

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ABSTRACT The antileishmanial efficacy of four novel quinoline derivatives was determined in vitro against Leishmania chagasi, using extracellular and intracellular parasite models. When tested against L. chagasi-infected macrophages, compound 3b demonstrated 8.3-fold greater activity than did the standard pentavalent antimony. No significant activity was found for compounds 3a, 4a, and 4b. The antilesihmanial effect of compound 3b was independent of host cell activation, as demonstrated by nitric oxide production. Ultrastructural studies of promastigotes treated with compound 3b showed mainly enlarged mitochondria, with matrix swelling and reduction in the number of cristae. Synthetic analogues based on the quinoline ring structure, already an established template for antiparasitic drugs, could provide further useful compounds.
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43

Heydari, Zahra, Maryam Mohammadi-Khanaposhtani, Somaye Imanparast, Mohammad A. Faramarzi, Mohammad Mahdavi, Parviz R. Ranjbar, and Bagher Larijani. "Pyrano[3,2-c]quinoline Derivatives as New Class of α-glucosidase Inhibitors to Treat Type 2 Diabetes: Synthesis, in vitro Biological Evaluation and Kinetic Study." Medicinal Chemistry 15, no. 1 (January 7, 2019): 8–16. http://dx.doi.org/10.2174/1573406414666180528110104.

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Background: Pyrano[3,2-c]quinoline derivatives 6a–n were synthesized via simple two-step reactions and evaluated for their in vitro α-glucosidase inhibitory activity. </P><P> Methods: Pyrano[3,2-c]quinoline derivatives 6a–n derivatives were prepared from a two-step reaction: cycloaddition reaction between 1-naphthyl amine 1 and malonic acid 2 to obtain benzo[h]quinoline-2(1H)-one 3 and reaction of 3 with aryl aldehydes 4 and Meldrum’s acid 5. The anti- α-glucosidase activity and kinetic study of the synthesized compounds were evaluated using α-glucosidase from Saccharomyces cerevisiae and p-nitrophenyl-a-D-glucopyranoside as substrate. The α-glucosidase inhibitory activity of acarbose was evaluated as positive control. Results: All of the synthesized compounds, except compounds 6i and 6n, showed more inhibitory activity than the standard drug acarbose and were also found to be non-cytotoxic. Among the synthesized compounds, 1-(2-bromophenyl)-1H-benzo[h]pyrano[3,2-c]quinoline-3,12(2H,11H)-dione 6e displayed the highest α-glucosidase inhibitory activity (IC50 = 63.7 ± 0.5 µM). Kinetic study of enzyme inhibition indicated that the most potent compound, 6e, is a non-competitive inhibitor of α-glucosidase with a Ki value of 72 µM. Additionally, based on the Lipinski rule of 5, the synthesized compounds were found to be potential orally active drugs. Conclusion: Our results suggest that the synthesized compounds are promising candidates for treating type 2 diabetes.
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T G, Shruthi, Sangeetha Subramanian, and Sumesh Eswaran. "Design, Synthesis and Study of Antibacterial and Antitubercular Activity of Quinoline Hydrazone Hybrids." Heterocyclic Communications 26, no. 1 (October 15, 2020): 137–47. http://dx.doi.org/10.1515/hc-2020-0109.

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AbstractEmerging bacterial resistance is causing widespread problems for the treatment of various infections. Therefore, the search for antimicrobials is a never-ending task. Hydrazones and quinolines possess a wide variety of biological activities. Herewith, eleven quinoline hydrazone derivatives have been designed, synthesized, characterized and evaluated for their antibacterial activity and antitubercular potential against Mtb WT H37Rv. Compounds QH-02, QH-04 and QH-05 were found to be promising compounds with an MIC value of 4 μg/mL against Mtb WT H37Rv. Compounds QH-02, QH-04, QH-05, and QH-11 were also found to be active against bacterial strains including Acinetobacter baumanii, Escherichia coli and Staphylococcus aureus. Further, we have carried out experiments to confirm the cytotoxicity of the active compounds and found them to be non-toxic.
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45

Tasqeeruddin, Syed, Yahya Asiri, and Jaber Abdullah Alsherhri. "An Efficient and Green Microwave-Assisted Synthesis of Quinoline DerivativesviaKnoevengal Condensation." Letters in Organic Chemistry 17, no. 2 (January 7, 2020): 157–63. http://dx.doi.org/10.2174/1570178616666190618153721.

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:We have developed an efficient and green synthesis of quinoline derivatives using L-proline under Knoevenagel condensation. L-proline was found to be an efficient catalyst for the Knoevenagel condensation of substituted 2-aminoaryl ketones 1 with the active methylene compounds 2, affording quinolone derivatives 3. The reaction has been done under conventional as well as under microwave conditions. The latter procedure has been found to be much more efficient in terms of time and yield.
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46

Venugopala, Katharigatta N., Vijayakumar Uppar, Sandeep Chandrashekharappa, Hassan H. Abdallah, Melendhran Pillay, Pran Kishore Deb, Mohamed A. Morsy, et al. "Cytotoxicity and Antimycobacterial Properties of Pyrrolo[1,2-a]quinoline Derivatives: Molecular Target Identification and Molecular Docking Studies." Antibiotics 9, no. 5 (May 7, 2020): 233. http://dx.doi.org/10.3390/antibiotics9050233.

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A series of ethyl 1-(substituted benzoyl)-5-methylpyrrolo[1,2-a]quinoline-3-carboxylates 4a–f and dimethyl 1-(substituted benzoyl)-5-methylpyrrolo[1,2-a]quinoline-2,3-dicarboxylates 4g–k have been synthesized and evaluated for their anti-tubercular (TB) activities against H37Rv (American Type Culture Collection (ATCC) strain 25177) and multidrug-resistant (MDR) strains of Mycobacterium tuberculosis by resazurin microplate assay (REMA). Molecular target identification for these compounds was also carried out by a computational approach. All test compounds exhibited anti-tuberculosis (TB) activity in the range of 8–128 µg/mL against H37Rv. The test compound dimethyl-1-(4-fluorobenzoyl)-5-methylpyrrolo[1,2-a]quinoline-2,3-dicarboxylate 4j emerged as the most promising anti-TB agent against H37Rv and multidrug-resistant strains of Mycobacterium tuberculosis at 8 and 16 µg/mL, respectively. In silico evaluation of pharmacokinetic properties indicated overall drug-likeness for most of the compounds. Docking studies were also carried out to investigate the binding affinities as well as interactions of these compounds with the target proteins.
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47

Kuchař, Miroslav, Vojtěch Kmoníček, Vladimíra Panajotová, Antonín Jandera, Bohumila Brunová, Richard Junek, Věra Bucharová, Jan Čejka, and Dalibor Šatinský. "Derivatives of (Phenylsulfanyl)benzoic Acids with Multiple Antileukotrienic Activity." Collection of Czechoslovak Chemical Communications 69, no. 11 (2004): 2098–120. http://dx.doi.org/10.1135/cccc20042098.

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A series of derivatives of (phenylsulfanyl)benzoic acids bearing quinoline, 2,4-dihydroxy-3-propylacetophenone and 2,4-difluorobiphenyl moieties were prepared and their antileukotrienic activities evaluated. Some of the compounds were found to display multiple antileukotrienic effect in the inhibition of LTB4biosynthesis, binding to LTD4and LTB4receptors, superior to the standards (zileuton and zafirlukast) used. The compounds had an antiinflammatory effect, manifested with quinoline derivatives by a significant inhibition of bronchospasm induced by LTD4and/or albumin. The results of regression analysis correspond to the observation that the most active compounds belong to quinoline derivatives with the lowest lipophilicity. X-ray analysis of the quinoline compounds revealed that an intramolecular hydrophobic interaction of their aromatic rings does not occur in the solid state.
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48

Singh, Archana, Karuna S. Shukla, and Monika Chaudhary. "Design, Synthesis and Characterization of Novel Quinoline Derivatives from Substituted Acetophenone as an Antioxidant Agent." Natural Products Journal 10, no. 4 (August 21, 2020): 495–501. http://dx.doi.org/10.2174/2210315509666190725141334.

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Background:: In a search for new antioxidant agents, a series of eleven diversely substituted quinoline containing chalcone derived from a quinoline scaffold were synthesized and evaluated as antioxidant agents. Methods:: Compounds were prepared via Claisen-Schmidt condensations of 2, 6-dichloroquinoline- 3-carbaldehyde with appropriately substituted acetophenones. All the synthesized compounds were characterized by spectral (FTIR, mass by ESI and 1H NMR) and elemental analysis. The synthesized compounds were investigated for their in vitro antioxidant activity by FRAP assay method. Results:: Among the screened compounds QHM-1, QH-1, QDB-1 and QE-1 exhibited significant antioxidant activities. Conclusion:: It can be predicted that electron releasing groups with higher resonating structures makes the compound more potent than the compounds with electron releasing group and less resonating structures. The electron releasing behavior of compounds proved them good terminators of radical chain reactions.
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Peerzade, Nargisbano Ayyub, Shravan Yegu Jadhav, Raghunath Bhikaji Bhosale, Amol Anantrao Kulkarni, and Bhushan Dnyandeo Varpe. "Synthesis, Docking, in silico ADMET and Pharmacological Evaluation of Some N-acetyl Pyrazole and Quinoline Conjugates." Letters in Drug Design & Discovery 17, no. 8 (July 29, 2020): 1015–26. http://dx.doi.org/10.2174/1570180817666200228123347.

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Background: Pyrazolines are reported having anti-inflammatory, anti-oxidant and antidiabetic activities in the literature. Drugs like celecoxib, antipyrine, etc. are structurally similar to the designed compounds. Objectives: To synthesize and characterize N-acetyl pyrazole and quinoline conjugates and test them for Anti-inflammatory, Antioxidant, Antibacterial, Antiamylase and Antimalarial activities. Methods: A series of methoxy substituted quinoline based pyrazoline derivatives (2a-2j) were synthesized in good to excellent yield from corresponding quinoline chalcones (1a-1j). The synthesized compounds were characterized and screened for their in vitro anti-inflammatory, antioxidant, antiamylase, antibacterial and antimalarial activities. Docking and in silico ADMET studies were performed with PDB: 3LN1. Results: Compounds 2b, 2i and 2j showed significant anti-inflammatory activity as compared to standard sodium diclofenac. All compounds (2a-2j) showed excellent antioxidant activity for DPPH even more than standard ascorbic acid. Compounds 2e, 2f, 2h and 2i showed excellent antioxidant activity for NO. as compared to standard ascorbic acid. Compound 2f showed significant antioxidant activity for SOR. Almost all the compounds showed significant antibacterial as well as anti-amylase activity with few exceptions, whereas compounds 2f, 2h and 2j showed potent antimalarial activity. Conclusion: Compounds have shown good anti-inflammatory activities as compared with diclofenac. All the synthesized pyrazoline derivatives showed excellent anti-amylase activity as compared to standard acarbose. Also, compounds have shown good antioxidant antibacterial and antimalarial activities.
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Naga Raju, Gollapalli. "GREEN SYNTHESIS, CHARACTERIZATION, AND ANTHELMINTHIC ACTIVITY OF NEWER QUINOLINE DERIVATIVES CONTAINING ACRIDINE MOIETY." Asian Journal of Pharmaceutical and Clinical Research 10, no. 9 (September 1, 2017): 377. http://dx.doi.org/10.22159/ajpcr.2017.v10i9.17226.

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Objectives: Synthesis of newer 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(2-chloro-6-substituted-quinolin-3-yl)-acridine-1,8(2H,5H,9H,10H)-diones were synthesized by reacting 5,5-dimethylcyclohexane-1,3-dione with substituted 2-chloro-quinoline-3-carbaldehyde in presence of ammonium acetate.Methods: Synthesis was carried out by microwave irradiation method and the synthesized compounds have been characterized using elemental analysis, FT-IR, 1H NMR, and 13C NMR spectroscopy and further supported by mass spectroscopy. Purity of all the compounds has been checked on thin layer chromatographic plate and high-performance liquid chromatography technique. All the synthesized compounds were tested for antibacterial and anthelminthic activities.Results: The results were revealed that the compounds AQ-4 and AQ-5 have showed good activity against both Gram-positive and Gram-negative bacteria. Compounds AQ-4 and AQ-5 showed moderate activity against all the organisms. However, all the derivatives have shown less antibacterial activity when compared to the standard drug amikacin. The compounds AQ-3 and AQ-5 showed good anthelminthic activity and compounds AQ-9 and AQ-10 showed moderate anthelminthic activity. However, all the compounds have shown less anthelmintic activity when compared to the standard drug albendazole.Conclusion: The study reveals that compounds containing quinoline derivatives with acridine moiety shown the antibacterial activity against the pathogens Bacillus subtilis, Bacillus cereus, Staphylococcus epidermidis, Salmonella typhi, Pseudomonas aeruginosa and Klebsiella pneumoniae. These derivatives also possess the good anthelmintic activity. The above green synthesis technique could be a right solution for industrial applications in the future and therapeutic needs.
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