Relevant bibliographies by topics / Quinoline compounds

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Academic literature on the topic 'Quinoline compounds'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Quinoline compounds"

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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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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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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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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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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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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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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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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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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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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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Dissertations / Theses on the topic "Quinoline compounds"

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Abner, Erik 1986. "Identification of HIV-1 reactivating quinoline compounds as bromodomain inhibitors." Doctoral thesis, Universitat Pompeu Fabra, 2016. http://hdl.handle.net/10803/565528.

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Tras la infección por VIH-1, el establecimiento de un depósito de células T en reposo infectadas latentemente con VIH impide la erradicación del virus en pacientes. Para lograr la erradicación, la terapia retroviral existente debe combinarse con medicamentos que reactiven los virus latentes. Previamente, nuestro grupo describió un nuevo compuesto químico, MMQO (8-metoxi-6-metilquinolin-4-ol) que es capaz de reactivar la transcripción viral a través de un mecanismo desconocido. El objetivo de este proyecto fue identificar los proteínas que interaccionan con MMQO e investigar su papel en la reactivación del VIH-1. Hemos establecido que MMQO es capaz de inducir la transcripción de minigenomas provirales que carecen de genes para los componentes virales, lo que nos permite plantear la hipótesis de que el compuesto funciona principalmente a través de factores del huésped. La caracterización de los perfiles de transcripción de MMQO mediante microarrays de expresión nos permitió identificar numerosos rasgos provocados por el compuesto. MMQO muestra una robusta naturaleza inmunosupresora que afecta a la proliferación celular debido a la disminución de los niveles proteicos de cMyc y Bcl-2 y la desregulación de genes sensibles a acetilación. Estas características indican que MMQO imita las lisinas acetiladas de histonas y funciona como un inhibidor de bromodominio y dominio extraterminal (BET). Análisis adicionales de la expresión génica y proteómica confirmaron esta hipótesis y demostramos que MMQO desplaza de la cromatina a Brd4, un miembro de la familia BET y antagoniza el papel pro-latente de Brd4 cerca del sitio de inicio de la transcripción de VIH-1. Modelos computacionales de docking también confirmaron la especificidad de MMQO hacia los bromodominios de la familia BET y un ensayo in vitro mediante FRET contra los miembros de la familia, identificó que MMQO tiene una mayor afinidad hacia la proteína Brd9. Por último, hemos establecido que la inhibición de Brd9 tiene un mínimo efecto sobre la expresión proviral, lo que sugiere que la principal función de MMQO sobre VIH-1 se puede atribuir al desplazamiento de Brd4. Debido a la amplia gama de propiedades de los inhibidores de la familia BET, estas moléculas se están evaluando actualmente en ensayos clínicos contra diversos tipos de cáncer y afecciones inmunitarias. MMQO, con un funcionamiento dual, es un nuevo miembro de esta clase de medicamentos. La estructura minimalista de MMQO puede ser muy prometedora ya que puede ser modificada para optimizar la afinidad hacia Brd9 / 4 y, potencialmente, podría ser de utilidad en la investigación contra una gran variedad de enfermedades, incluyendo el VIH.
Upon HIV-1 infection, a reservoir of HIV latently infected resting T cells prevents the eradication of the virus from patients. To achieve eradication, the existing virus suppressing antiretroviral therapy must be combined with drugs that reactivate the dormant viruses. Our group previously described a novel chemical scaffold compound, MMQO (8-methoxy-6-methylquinolin-4-ol), which is capable of reactivating viral transcription through an unknown mechanism. The objective of this project was to identify the molecular binding partners of MMQO and elaborate their role in the reactivation of HIV-1. We established that MMQO is capable of inducing HIV-1 independently of viral proteins by inducing transcription from proviral minigenomes lacking genes for viral components, allowing us to hypothesize that the compound primarily functions through host factors. Characterizing MMQO’s transcriptional profiles with total mRNA expression microarrays, we were able to identify numerous traits provoked by the drug. MMQO displayed a robust immunosuppressive nature, it affected cell proliferation by diminishing cMyc and Bcl-2 protein levels and increased the dysregulation of acetylation sensitive genes. These hallmarks indicated that MMQO mimics acetylated lysines of core histones and functions as a bromodomain and extraterminal domain (BET) protein family inhibitor. Further gene expression and proteomic analysis confirmed this supposition and we demonstrated that MMQO deposes of the BET family member Brd4 from global chromatin and antagonizes the pro-latent role of Brd4 near the transcription start site of HIV-1. Computational docking models also confirmed MMQO’s specificity towards the BET family bromodomains and an in vitro screening against the family members by FRET identified MMQO to have the highest affinity towards the Brd9 protein. Finally, we established that the inhibition of Brd9 had minimal effect on the proviral expression, suggesting that the primary function of MMQO on HIV-1 can be attributed to the displacement of Brd4. Due to the broad range of properties characteristic to BET family inhibitors, these molecules are currently being evaluated in clinical trials against various types of cancers and immune conditions. The dual functioning scaffold compound MMQO is a new member of this class of drugs. The minimalistic structure of MMQO shows promise for it to be further optimized for higher affinities towards Brd9 / 4 and could potentially be of use in research against a variety of diseases, including HIV.
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Pakade, Vusumzi Emmanuel. "Application of the Baylis-Hillman reaction in the preparation of quinoline derivatives." Thesis, Rhodes University, 2006. http://hdl.handle.net/10962/d1007669.

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The reaction of various 2-nitrobenzaldehyde derivatives with methyl vinyl ketone (MVK) in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) has afforded the Baylis-Hillman adducts in moderate to good yield. Dissolution of the catalyst in the solvent before the addition of the aldehyde was observed to improve the yield. Reduction of the Baylis-Hillman adducts was effected by catalytic hydrogenation using a 10% palladium-on- carbon catalyst in ethanol to give quinoline and quinoline-N-oxide derivatives and, in some cases, acyclic reduction products. All products were characterised using NMR and, where appropriate, HRMS methods. Selected quinoline-N-oxides were successfully converted to their corresponding quinoline derivatives using phosphorus tribromide (PBr₃) and DMF as solvent. Conjugate addition of the benzylamine and piperidine nucleophiles to the Baylis-Hillman adducts was also investigated but proved problematic, with one of the substrates undergoing a retro-Baylis-Hillman reaction to afford the aldehyde in ca. 40% yield, but seemingly only traces of the required product. Perkin-type coupling of two 2-methylquinolines with benzaldehyde was successfully effected to afford the desired styrylquinoline derivatives confirming the potential of the Baylis-Hillman approach to the construction of the analogues of known HIV-1 integrase inhibitors. Three ¹³C NMR chemical shift prediction programmes, viz., Chem Window, neural network and HOSE (hierarchically ordered spherical description of environment) methods were applied to selected representative compounds prepared in the project. The results from the three programmes correlated reasonably well with the experimental carbon-13 chemical shift data for each of the selected compounds.
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Harris, Tyler. "Photo-induced isomerization and dimerization of various styryl quinolines." View electronic thesis (PDF), 2009. http://dl.uncw.edu/etd/2009-2/harrist/tylerharris.pdf.

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Banini, Serge R. "Palladium-catalyzed syntheses of indoles, pyrroloindoles, quinolines a base-mediated formation of N-alkoxyindoles, and progress toward the first total synthesis of echinosulfone A /." Morgantown, W. Va. : [West Virginia University Libraries], 2008. https://eidr.wvu.edu/etd/documentdata.eTD?documentid=5710.

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Thesis (Ph. D.)--West Virginia University, 2008.
Title from document title page. Document formatted into pages; contains xv, 275 p. : ill. Includes abstract. Includes bibliographical references (p. 107-113).
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Kaschula, Catherine Hart. "Haematin-Quinoline interactions and structure-activity relationships in the antimalarial chloroquine and related compounds." Doctoral thesis, University of Cape Town, 2002. http://hdl.handle.net/11427/6316.

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Includes bibliographical references.
The nature of the ferriprotoporphyrin IX (Fe(III)PPIX) antimalarial drug target and its interactions with aminoquinolines was investigated spectrophotometrically. The antiquity of malaria, which is caused by protozoan parasites of the genus Plasmodium, is demonstrated by the host specificity of over 100 parasite species found in reptiles, birds and mammals. The four species of plasmodia that infect man are P. vivax, P. malariae, P. ovale and P. falciparum; of which P. falciparum is the most deadly (Bruce-Chwatt 1981 ).
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Evans, Alba Pilar. "New Ruthenium(II) Polypyridyl Compounds with Quinoline Type Ligands for the Treatment of Cutaneous Leishmaniasis." The Ohio State University, 2017. http://rave.ohiolink.edu/etdc/view?acc_num=osu1511881725973833.

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Huang, Jinqing, and 黃普卿. "A study of the reaction mechanisms and reactive intermediates involved in halogenated compounds : trichloroethylene oxide, halogenated benzophenones, and halogenated quinoline-based phototriggers." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2014. http://hdl.handle.net/10722/208036.

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UV/Vis absorption spectroscopy (UV/Vis), femtosecond transient absorption spectroscopy (fs-TA), nanosecond transient absorption spectroscopy (ns-TA), and nanosecond time-resolved resonance Raman spectroscopy (ns-TR3), as well as density functional theory (DFT) computations were employed to study the mechanisms and the intermediates in reactions of selected halogenated compounds, including trichloroethylene oxide (TCE oxide), halogenated benzophenones (4-FBP, 4-ClBP, 4-BrBP, 3-FBP, 33’-DFBP, 3-ClBP, 3-BrBP, 2-FBP, 2-ClBP, and 2-BrBP), and halogenated quinoline-based phototriggers (BHQ-OPh and BHQ-OAc). This study investigated the halogen substituent effect on the mechanisms of various water-involved reactions and the influences from the number of halogens present, the type of halogen and the substituent position of the halogen in the molecules of interest. The general mechanisms for the reactions of these halogenated compounds were summarized along with discussion of the driving forces from the substituted halogen. First, TCE oxide was hydrolyzed to release chloride ions one by one which led to a complicated water-catalyzed decomposition. To account for the dehalogenation and the formation of CO with three kinds of carboxylic acids (formic acid, glyoxylic acid, and dichloroacetic acid), the predominant decomposition pathways were examined by comparing the computed activation energies for the formation of different products. From these comparisons, the ring-opening reaction was identified as the rate-determining step, which is also supported by previous experimental observations reported in the literature. Based on all of these analyses, the mechanisms of the water-catalyzed decomposition reactions were determined and a water-assisted HCl elimination model has been proposed. Second, some halogen-substituted benzophenones demonstrated an efficiency for a photosubstitution reaction and the related photohydration reactions. Interestingly, the efficient photosubstitution reactions of 3-FBP and 33’-DFBP were dependent on the solution acidity and reached a maximum in 1 M HClO4 CH3CN/H2O (1/1) solution. Only the photohydration reaction took place for the 3-ClBP, 3-BrBP, 4-FBP, 4-ClBP, and 4-BrBP molecules. Nevertheless, no special photochemical reaction occurred for 2-FBP, 2-ClBP, and 2-BrBP. The mechanisms and intermediates were directly characterized by spectroscopic observations and rationalized by results from DFT computations. According to these results, the general mechanisms for the photosubstitution reaction and the related photohydration reactions of halogenated benzophenone derivatives were summarized. These results reveal that the efficiency in forming the corresponding hydroxy benzophenone is influenced by the solution acidity, substituent positions, and the character of the substituted halogens. The substituted halogen is the driving force of this photosubstitution reaction. This conclusion provides insight into several possible applications that are also briefly discussed in this thesis. Lastly, the BHQ-OPh system was found to undergo an extraordinary efficient excited-state proton transfer (ESPT) to initiate a dehalogenation reaction. The fs-TA and ns-TA spectra indicate clearly the interactions between four prototropic forms of BHQ-OPh, which were characterized by UV-Vis spectra under different pH values. These prototropic forms play important roles in inducing further dehalogenation, thus their structural configurations were also investigated by DFT computations. Besides, competing with the dehalogenation reaction, BHQ-OAc underwent another photodeprotection to release the OAc group. The comparison between BHQ-OPh and BHQ-OAc provides further information in understanding the mechanisms of dehalogenation reactions and photodeprotection reactions of these quinoline-based phototriggers.
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Chemistry
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Doctor of Philosophy
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8

Vezmar, Marko. "Pharmacological effects of quinoline-related compounds in human tumour cells overexpressing the multidrug resistance protein (MRP)." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 1997. http://www.collectionscanada.ca/obj/s4/f2/dsk2/tape16/PQDD_0003/MQ37175.pdf.

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Tittle, James Alfred. "Ab Initio Studies of High Temperature Pyrolysis Mechanisms in Heterocyclic Nitrogen-Containing Compounds." Digital Commons @ East Tennessee State University, 2000. https://dc.etsu.edu/etd/21.

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The decomposition mechanisms of various coal constituents undergoing pyrolysis are of great concern in environmental circles (especially those coal constituents containing nitrogen). Most methods of burning coal that are efficient involve doing so at high temperatures. This invariably results in a large portion of non-combusting coal being heated to high temperatures also causing pyrolysis of the original coal constituents. The end result of such pyrolysis is the production of a number of noxious gaseous products. If we are to design methods of reducing the amount of toxins that are produced from the industrial use of coal, it is necessary to understand the pyrolysis process mechanistically. Due to the great number of coal constituents, a reasonable approach to such a mechanistic study is to use a simpler model. Pyridine makes an excellent starting model upon which to build. Our study focuses on interpretation of proposed reaction channels from experimental work on pyridine, quinoline and isoquinoline shock-tube decomposition in light of new ab initio energy calculations using Gaussian 98. The pathways thus determined support the proposed pyrolysis mechanisms and agree with experimental evidence obtained from independent groups of researchers performing shock tube pyrolysis.
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10

Gibhard, Liezl. "The effect of Pheroid™ technology on the bioavailability of quinoline-based anti-malarial compounds in primates." Thesis, North-West University, 2012. http://hdl.handle.net/10394/9025.

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Resistance against anti-malarial drugs remains one of the greatest obstacles to the effective control of malaria. The current first-line treatment regimen for uncomplicated P.falciparum malaria is based on artemisinin combination therapies (ACTs). However, reports of an increase in tolerance of the malaria parasite to artemisinins used in ACTs have alarmed the malaria community. The spread of artemisinin-resistant parasites would impact negatively on malaria control. Chloroquine and amodiaquine are 4-aminoquinolines. Chloroquine and amodiaquine were evaluated in a primate model by comparing the bioavailability of these compounds in a reference formulation and also in a Pheroid® formulation. In vivo pharmacokinetic studies were conducted for chloroquine, and in vitro and in vivo drug metabolism and pharmacokinetic (DMPK) studies were conducted for amodiaquine. Pheroid® technology forms the basis of a colloidal drug delivery system, and it is the potential application of this technology in combination with the 4-aminoquinolines that was the focus of this thesis. Pheroid® is a registered trademark but for ease of reading will be referred to as pheroid(s) or pro-pheroid(s) throughout the rest of the thesis. The non-human primate model used for evaluation of the pharmacokinetic parameters was the vervet monkey (Chlorocebus aethiops). Chloroquine was administered orally at 20 mg/kg. A sensitive and selective LC-MS/MS method was developed to analyze the concentration of chloroquine in both whole blood and plasma samples. The Cmax obtained for whole blood was 1039 ± 251.04 ng/mL for the unformulated reference sample of chloroquine and 1753.6 ± 382.8 ng/mL for the pheroid formulation. The AUC0-inf was 37365 ± 6383 ng.h/mL (reference) and 52047 ± 11210 ng.h/mL (pheroid). The results indicate that the use of pheroid technology enhances the absorption of chloroquine. The effect of pheroid technology on the bioavailability of amodiaquine and N-desethylamodiaquine was determined in two groups of vervet monkeys, with the reference group receiving capsules containing the hydrochloride salt of amodiaquine and the test group receiving capsules containing a pro-pheroid formulation of amodiaquine. Amodiaquine was administered at 60 mg/kg. Blood concentrations of amodiaquine and N-desethylamodiaquine samples were monitored over 13 time points from 0.5 to 168 hours. Amodiaquine and pro-pheroid formulated amodiaquine were incubated in vitro with human and monkey liver (HLM and MLM) and intestinal (HIM and MIM) microsomes and recombinant cytochrome P450 enzymes. The in vitro metabolism studies confirm the rapid metabolism of amodiaquine to the main metabolite N-desethylamodiaquine in monkeys. Although the pharmacokinetic parameters varied greatly, parameters for both the parent compound and main metabolite were lower in the test formulation compared to the reference formulation. For HLM, MLM and CYP2C8, the pro-pheroid test formulation showed significantly longer amodiaquine clearance and slower formation of N-desethylamodiaquine. However, the effect was reversed in MIM. Pheroid technology impacts differently on the bioavailability of the various pharmaceutical classes of anti-malarials. Pheroid technology did not enhance the bioavailability of amodiaquine or N-desethylamodiaquine. This is contrary to the observed effects of pheroid technology on the pharmacokinetics of other drugs such as artemisone and chloroquine where it increases the area under the curve and prolongs the drug half-life.
Thesis (PhD (Pharmaceutics))--North-West University, Potchefstroom Campus, 2013.
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Books on the topic "Quinoline compounds"

1

Ronne, Erik. Synthesis of imidazoazaarenes. Uppsala, Sweden: Swedish University of Agricultural Sciences, Dept. of Chemistry, 1994.

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Jones, Gurnos. Quinolines, Part 1. Wiley & Sons, Incorporated, John, 2009.

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Jones, Gurnos. Quinolines, Part 2. Wiley & Sons, Incorporated, John, 2009.

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The World Market for Heterocyclic Compounds with Nitrogen Hetero-Atom(s) Only, Containing a Quinoline or Isoquinoline Ring-System Not Further Fused: A 2004 Global Trade Perspective. Icon Group International, Inc., 2005.

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Parker, Philip M. The 2007 Import and Export Market for Heterocyclic Compounds with Nitrogen Hetero-Atom(s) Only, Containing a Quinoline or Isoquinoline Ring-System Not Further Fused in China. ICON Group International, Inc., 2006.

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Parker, Philip M. The 2007 Import and Export Market for Heterocyclic Compounds with Nitrogen Hetero-Atom(s) Only, Containing a Quinoline or Isoquinoline Ring-System Not Further Fused in India. ICON Group International, Inc., 2006.

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Parker, Philip M. The World Market for Heterocyclic Compounds with Nitrogen Hetero-Atom(s) Only, Containing a Quinoline or Isoquinoline Ring-System Not Further Fused: A 2007 Global Trade Perspective. ICON Group International, Inc., 2006.

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Greenhill, John V. The Chemistry of Heterocyclic Compounds, Quinolines. Wiley-Interscience, 1990.

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Parker, Philip M. The 2007 Import and Export Market for Heterocyclic Compounds with Nitrogen Hetero-Atom(s) Only, Containing a Quinoline or Isoquinoline Ring-System Not Further Fused in United States. ICON Group International, Inc., 2006.

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Book chapters on the topic "Quinoline compounds"

1

Greenhill, John V. "Quinoline Aldehydes." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 1–87. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470187043.ch1.

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Greenhill, John V. "Quinoline Ketones." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 89–516. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470187043.ch2.

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Jones, Gurnos. "Synthesis of the Quinoline Ring System." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 93–318. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470187029.ch2.

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Jones, Gurnos. "The Physical and Chemical Properties of Quinoline." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 1–92. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470187029.ch1.

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Pardasani, R. T., and P. Pardasani. "Magnetic properties of cobalt(II) 3-methylbenzoate adduct with quinoline." In Magnetic Properties of Paramagnetic Compounds, 752–53. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-54231-6_409.

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Pardasani, R. T., and P. Pardasani. "Magnetic properties of cobalt(II) 3-bromobenzoate adduct with quinoline." In Magnetic Properties of Paramagnetic Compounds, 758. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-54231-6_414.

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Pardasani, R. T., and P. Pardasani. "Magnetic properties of nickel(II) 3-methylbenzoate adduct with quinoline." In Magnetic Properties of Paramagnetic Compounds, 50. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-54234-7_21.

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Pardasani, R. T., and P. Pardasani. "Magnetic properties of nickel(II) 3-chlorobenzoate adduct with quinoline." In Magnetic Properties of Paramagnetic Compounds, 53. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-54234-7_24.

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Pardasani, R. T., and P. Pardasani. "Magnetic properties of nickel(II) 3-bromobenzoate adduct with quinoline." In Magnetic Properties of Paramagnetic Compounds, 54. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-54234-7_25.

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Pardasani, R. T., and P. Pardasani. "Magnetic properties of nickel(II) 3-nitrobenzoate adduct with quinoline." In Magnetic Properties of Paramagnetic Compounds, 57. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-54234-7_28.

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Conference papers on the topic "Quinoline compounds"

1

Ustinov, Ilya, Nikolaj Khlytin, Yurij Atroshchenko, and Irina Shahkeldyan. "NEW THIAZOL DERIVATIVES CONTAINING NITRO QUINOLINE FRAGMENT." In Chemistry of nitro compounds and related nitrogen-oxygen systems. LLC MAKS Press, 2019. http://dx.doi.org/10.29003/m797.aks-2019/383-384.

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Christie, D. J., H. Diaz-Arauzo, and J. M. Cook. "REACTIONS OF DRUG-DEPENDENT ANTIBODIES WITH METABOLITES OF QUININE (Qn) AND QUINIDINE (Qd)." In XIth International Congress on Thrombosis and Haemostasis. Schattauer GmbH, 1987. http://dx.doi.org/10.1055/s-0038-1644578.

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In many cases of drug-induced immunologic thrombocytopenia (DITP), a metabolite, rather than the native drug, is suspected of provoking the destructive drug-dependent antibodies (DDAB) responsible for this severe hemorrhagic disorder. However, this has not previously been investigated for Qn- and Qd-DDAB. We report evidence that the native drugs, and not their metabolites, are the provocative agents in Qn and Qd DITP. Reactions of Qn- and Qd-DDAB with platelets were studied with the native drugs and four of their metabolites: the N-oxide and 10,11-diol derivatives (quinuclidine ring modifications), the des-methyl derivatives (aromatic quinoline ring modification), and 2'-quininone and 2'-quinidinone (2'-oxo derivatives) (also quinoline ring modifications on Qn and Qd, respectively). Five antibodies were studied:two Group 1 DDAB (specific for compounds with native configuration at asymmetric carbon positions), two Group 2 DDAB (similar to Group 1 DDAB but also known to require the methoxy group on the quinuclidine ring for full activity), and one Group 3 DDAB (reactive with the native drug, its stereoisomer, and several nonmetabolic analogs of both compounds) . Using a complement-dependent 51Cr-lysis assay, the reactions of all DDAB with platelets and the four metabolites were similar to 100-fold weaker when compared to reactions obtained with the native drug, with these exceptions:Group 2 DDAB failed to react with the desmethyl and 2'-oxo metabolites and the Group 3 DDAB failed to react with 2'-oxo Qd. This observation shows that the activity of certain DDAB is critically dependent on the native quinoline ring structure. Importantly, none of the DDAB reacted more strongly with any of the metabolites tested when compared with reactions in the presence of the native drug. These findings indicate that DDAB react with platelets preferentially in the presence of the unaltered Qn and Qd molecules and suggest that, while the role of metabolites cannot be entirely ruled out, the native structure of the drug molecule is sufficient to stimulate production of the antibodies responsible for DITP.
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Andrade, Karine N. de, Amanda R. P. Costa, Rodolfo I. Teixeira, Micaeli L. da S. Moreira, José Walkimar M. Carneiro, Nanci C. L. Garden, Fernanda da C. S. Boechat, Maria Cecília B. V. de Souza, Pedro N. Batalha, and Rodolfo G. Fiorot. "Photophysical characterization of 3-acyl-4-quinolones." In VIII Simpósio de Estrutura Eletrônica e Dinâmica Molecular. Universidade de Brasília, 2020. http://dx.doi.org/10.21826/viiiseedmol202006.

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4-quinolones derivatives can present fluorescent properties, depending on their substituents and on the chemical environment (e.g., acidic medium), allowing their application as ion sensors. We theoretically evaluated the photophysical properties of previously synthesized 3-acyl-4-quinolones to verify how different substituents (R1=H, NH2 and R2 = OEt, OH, NHPh) affect their absorption profiles and the emission profile of a reference compound, PB3. All DFT and TD-DFT calculations were performed at B3LYP-D3/6-311++G(d,p) level and continuum polarization model for simulated acetonitrile as solvent. For PB2 (R1 = H, R2 = OEt), we observed hypsochromic shift compared to PB3 due to the increase of the gap between HOMO/LUMO (absence of electron-donating group), in accordance with experimental data. For R1=NH2 and R2=OH, NHPh (PB6 and PB10, respectively), the gap between HOMO/LUMO increases, resulting in a soft bathochromic shift for the simulated absorption spectra. In addition, we evaluated the effect of acid addition on the absorption and emission profile of PB3 and the results were compared with experimental data. Our thermodynamic results suggest that protonation occurs on the endocyclic carbonyl of the quinolone moiety, probably due to an increased aromatic character, as suggested by our NICS calculations. Finally, we associate the increase of the fluorescence in the acidic medium to the establishment of an intramolecular hydrogen bond and, thus, increased rigidity.
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Manabe, S., H. Yanagisawa, S. Ishikawa, Y. Kitagawa, K. Tohyama, S. Abe, and O. Wada. "TRYPTOPHAN PYROLYSIS PRODUCTS FOUND IN COOKED FOODS INHIBIT HUMAN PLATELET AGGREGATION BY INHIBITING CYCLOOXYGENASE." In XIth International Congress on Thrombosis and Haemostasis. Schattauer GmbH, 1987. http://dx.doi.org/10.1055/s-0038-1643402.

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Humans are exposed to numerous toxic compounds in foods. During the past decade, several carcinogenic heterocyclic amines have been reported to be present in the cooked foods. Recently, we reported that some of the carcinogenic heterocyclic amines isolated from foods were present in human plasma. In order to know the effects of the carcinogens isolated from foods on the cell function, we investigated the effects of the carcinogenic heterocyclic amines including Trp-P-1(3-amino-l,4-dimethyl-5H-pyrido❘4,3-b❘indole) and Trp-P-2(3-amino-1-methyl-5H-pyrido❘4,3-b❘indole) on human platelet aggregation and polymorphonuclear leukocyte aggregation. Only tryptophan pyrolysis products, Trp-P-1 and Trp-P-2, had potent inhibitory effects on human platelet aggregation when platelets were preincubated with the carcinogens for 15 min. Other carcinogenic heterocyclic amines such as glutamic acid pyrolysates (Glu-P-1 and Glu-P-2) and 3H-imidazo ❘4,5-f❘quinoline-2-amines(IQ and MelQ) did show no effect on platelet aggregation even at 100 μM.The autoradiogram demonstrated that Tryptophan pyrolysis products, Trp-P-1 and Trp-P-2, dose-dependently inhibited the formation of HHT,PGD2,PGE2 and TXB2 induced by sodium arachidonate in human platelets labeled with ❘ 14c❘ arachidonic acid. Moreover, Trp-P-1 and Trp-P-2 did not show significant effects on leukocyte aggregation induced by sodium arachidonate (0.75mM) even at lOOnM. It is concluded that Trp-P-1 and Trp-P-2 isolated from cooked foodstuffs have potent inhibitory effects on the cyclo-oxygenase pathway of the platelet. Therefore, human platelet function might be affected with daily foods containing tryptophan pyrolysis products in vivo.
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Rylova, Gabriela, Petr Dzubak, Anna Janostakova, Ivo Frydrych, Petr Konecny, Dusan Holub, Tomas Ozdian, et al. "Abstract 4624: Molecular target identification of quinolinone based anticancer compounds." In Proceedings: AACR Annual Meeting 2014; April 5-9, 2014; San Diego, CA. American Association for Cancer Research, 2014. http://dx.doi.org/10.1158/1538-7445.am2014-4624.

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