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Journal articles on the topic '7-chloroquinoline'

Author: Grafiati

Published: 4 May 2022

Last updated: 5 May 2022

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1

Arsanious, Mona, Shaban Darwish, El-Sayed Shalaby, and Dina El-Ghwas. "Synthesis, X-ray, DFT Studies and Antimicrobial Properties of New Quinolinylphosphonates." Letters in Organic Chemistry 16, no. 8 (2019): 668–75. http://dx.doi.org/10.2174/1570178616666181231161801.

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The phosphorus atom in hexamethyl phosphorus triamide 5 attacks the carbonyl function in 2-chloroquinoline-3-carbaldehyde 4a to give the bis-quinolinyl ethanone product 6. On the other hand, quinoline ring-attack proceeds by the same phosphorus reagent upon reaction with 2-chloroquinoline- 3-aldoxime 4b yielding phosphonate 7. Meanwhile, the reaction of the tris-aminophosphine reagent 5 with 2-chloroquinoline- 3-(p-chlorophenyl)imine 4c affords the respective α-aminophosphonate 8. Moreover, the attack by phosphine 5 on 2-chloroquinoline-3-imines 4d and 4e produces the respective cyclic azophosphole derivatives 9a and 9b. [(2-chloroquinolin-3-yl)methylidene]propane dinitrile 4f reacts with phosphine 5 to yield [(2-chloroquinolinen-3-yl) 2,2-dicyanoethyl]tetramethylphosphonic diamide 10. Structural elucidations for the new products were based on compatible analytical and spectroscopic data. Moreover, the structures assigned for compounds 7 and 9a were unambiguously confirmed by X-ray crystallographic measurements. Biological evaluations indicated that compounds 4a,c exhibit antibacterial potency against Gram-positive bacteria and 4a,c and 9a show activity against Candida albicans strain.

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2

Motiwala, Hashim F., Raj Kumar, and Asit K. Chakraborti. "Microwave-Accelerated Solvent- and Catalyst-Free Synthesis of 4-Aminoaryl/alkyl-7-chloroquinolines and 2-Aminoaryl/alkylbenzothiazoles." Australian Journal of Chemistry 60, no. 5 (2007): 369. http://dx.doi.org/10.1071/ch06391.

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An efficient synthesis of 4-aminoaryl/alkyl-7-chloroquinolines and 2-aminoaryl/alkylbenzothiazoles has been developed by microwave-accelerated regioselective aromatic nucleophilic substitution of 4,7-dichloroquinoline and 2-chlorobenzothiazole with aromatic and aliphatic amines under solvent-free conditions in the absence of any added protic or Lewis acid catalyst. Chemoselective reaction with the amino group in preference to the phenolic hydroxy group was observed. Thus, the treatment of 4,7-dichloroquinoline (1 equiv.) with a mixture of aniline (2 equiv.) and phenol (2 equiv.) afforded exclusive formation of 4-aminophenyl-7-chloroquinoline. When 4,7-dichloroquinoline (1 equiv.) was separately treated with 2-aminophenol (2 equiv.) and 4-aminophenol (2 equiv.), 4-(2′-hydroxyphenyl)-7-chloroquinoline and 4-(4′-hydroxyphenyl)-7-chloroquinoline, respectively, were formed.

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3

Le, Trong Duc, Ngoc Nam Pham, and Tien Cong Nguyen. "Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives." Journal of Chemistry 2018 (2018): 1–7. http://dx.doi.org/10.1155/2018/4301847.

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N-(4-Substituted phenyl)acetamides, which were prepared from acetic anhydride and p-substituted anilines, were utilized as precursors for reactions to Vilsmeier-Haack reagent to form 6-substituted-2-chloroquinoline-3-carbaldehydes 3a–c. Meanwhile, a similar reagent was applied to 1-[1-(4-substituted phenyl)ethylidene]-2-phenylhydrazines as substrates, which were synthesized from phenylhydrazine hydrochloride and p-substituted acetophenones, and 1,3-diarylpyrazole-4-carbaldehydes 3d–f were observed as a result. Reactions between the aldehydes 3a–f and 7-chloro-4-hydrazinylquinoline 2, obtained from reaction of 4,7-dichloroquinoline 1 and hydrazine hydrate, formed six new hydrazone compounds, namely, 4-{2-[(6-substituted-2-chloroquinolin-3-yl)methylidene]hydrazinyl}-7-chloroquinolines 4a–c and 4-(2-{[3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl]methylene}hydrazinyl)-7-chloroquinolines 4d–f. The chemical structures of all synthesized compounds were elucidated by the analysis of IR, 1H, 13C-NMR, and HRMS spectral data. Additionally, all of the synthesized hydrazones were evaluated in terms of cytotoxic activity against four strains of bacteria and four strains of fungus at several concentrations of substrates. As a result, three of them, 4a–c, possess the good ability as growth inhibitor of Bacillus subtilis and Aspergillus niger at the concentration of 25 μg/mL and 50 μg/mL, respectively, while compound 4e only shows a cytotoxic activity against Aspergillus niger at the concentration of 25 μg/mL.

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4

Barlin, GB, SJ Ireland, TMT Nguyen, B. Kotecka, and KH Rieckmann. "Potential Antimalarials. XVIII. Some Mono- and Di-Mannich Bases of 3-[7-Chloro(and trifluoromethyl)quinolin-4-ylamino]phenol." Australian Journal of Chemistry 46, no. 11 (1993): 1685. http://dx.doi.org/10.1071/ch9931685.

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Syntheses are reported for mono- and di-Mannich base derivatives of 3-[7-chloro(and trifluoro-methyl)quinolin-4-ylamino]phenols by Mannich reaction on 3-[7-chloro(and trifluoromethyl )-quinolin-4-ylamino]phenols or by condensation of Mannich base derivatives of 3-aminophenol, prepared from 3-nitrophenol, with the appropriate 4-chloroquinoline. The antimalarial activity of 3-(7′-chloroquinolin-4′-ylamino)-2,6-bis[ pyrrolidin-1″-ylmethyl -(or piperidin-1″-ylmethyl)]phenol against the FC-27 isolate of Plasmodium falciparum was comparable to that of chloroquine, and it was not significantly diminished in tests against the chloroquine -resistant K-1 isolate.

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5

Yanni, Amal S., and Zarif H. Khalil. "Synthesis of some new 7-substituted aminomethyl-6-chloroquinoline-5,8-quinone." Collection of Czechoslovak Chemical Communications 56, no. 3 (1991): 702–5. http://dx.doi.org/10.1135/cccc19910702.

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6

Raj, Raghu, Anu Saini, Jiri Gut, Philip J. Rosenthal, and Vipan Kumar. "Synthesis and in vitro antiplasmodial evaluation of 7-chloroquinoline–chalcone and 7-chloroquinoline–ferrocenylchalcone conjugates." European Journal of Medicinal Chemistry 95 (May 2015): 230–39. http://dx.doi.org/10.1016/j.ejmech.2015.03.045.

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7

Yanni, Amal S., Zarif H. Khalil, and Ahmed A. Timmawy. "Synthesis of some new sulfonamide derivatives of 7-chloroquinoline-5,8-dione and pyridocarbazolediones." Collection of Czechoslovak Chemical Communications 56, no. 7 (1991): 1489–94. http://dx.doi.org/10.1135/cccc19911489.

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Interaction of 6-chloroquinoline-5,8-dione hydrochloride (I) or 6,7-dichloroquinoline-5,8-dione (II) with sulfa drug in ethanol containing diethylaniline afforded 7-substituted sulfonamide-10H-pyrido[3,2-b]carbazole-5,11-dione (III), and sulfonamide derivatives of 7-chloroquinoline-5,8-diones (IV). Moreover the reaction of II with arylamine in pyridine afforded substituted 6H-pyrido[2,3-b]carbazole-5,11-dione (V). The structure of the compounds was determined by elemental and spectral analysis, and by chemical reaction.

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8

Raj, Raghu, Jiri Gut, Philip J. Rosenthal, and Vipan Kumar. "1H-1,2,3-Triazole-tethered isatin-7-chloroquinoline and 3-hydroxy-indole-7-chloroquinoline conjugates: Synthesis and antimalarial evaluation." Bioorganic & Medicinal Chemistry Letters 24, no. 3 (2014): 756–59. http://dx.doi.org/10.1016/j.bmcl.2013.12.109.

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9

Devi, Kavita, Yumna Asmat, Sonika Jain, Swapnil Sharma, and Jaya Dwivedi. "An Efficient Approach to the Synthesis of Novel Oxazolidinones as Potential Antimicrobial Agents." Journal of Chemistry 2013 (2013): 1–5. http://dx.doi.org/10.1155/2013/252187.

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Oxazolidinone, either mononuclear or condensed with other heterocyclics, has established its importance in medicinal chemistry. A variety of biological activities have been reported by oxazolidinone derivatives. The present work describes the synthesis of several oxazolidinone derivatives, 3-(2-(7-chloroquinoline-4-ylamino)ethyl)-2-imino-5-(4-chloro/nitro/methoxy benzylidene)oxazolidin-4-one 4(a–c) and 4-(2-(7-chloroquinolin-4-ylamino)ethyl)-2(4-chloro/nitro/methoxy-benzylidene)-1,6-diox-4,9-di-azaspiro[4,4]nonane-3,8-dione 5(a–c). Synthesized compounds (1, 3, 4a, 5a, and 5c) were screened against bacterial strains such asS. aureus(MTCC 96) andE. coli(MTCC119) and fungal strainsA. niger(MTCC 1344) andC. albicans(MTCC 871) compared with penicillin for bacteria and fluconazole for fungi as reference drugs by disk diffusion method. All synthesized compounds were identified by the means of IR, NMR, and MS.

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10

Bueno, Juan, Fernando A. Rojas Ruiz, Santiago Villabona Estupinan, and Vladimir V. Kouznetsov. "In Vitro Antimycobacterial Activity of New 7-Chloroquinoline Derivatives." Letters in Drug Design & Discovery 9, no. 2 (2012): 126–34. http://dx.doi.org/10.2174/157018012799079761.

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11

Raj, Raghu, Christophe Biot, Séverine Carrère-Kremer, et al. "7-Chloroquinoline-isatin Conjugates: Antimalarial, Antitubercular, and Cytotoxic Evaluation." Chemical Biology & Drug Design 83, no. 5 (2014): 622–29. http://dx.doi.org/10.1111/cbdd.12273.

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12

Melis, Diana R., Christopher B. Barnett, Lubbe Wiesner, Ebbe Nordlander, and Gregory S. Smith. "Quinoline-triazole half-sandwich iridium(iii) complexes: synthesis, antiplasmodial activity and preliminary transfer hydrogenation studies." Dalton Transactions 49, no. 33 (2020): 11543–55. http://dx.doi.org/10.1039/d0dt01935f.

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Iridium(iii) half-sandwich complexes containing 7-chloroquinoline-1,2,3-triazole hybrid ligands were synthesised and their inhibitory activities evaluated against the Plasmodium falciparum malaria parasite.

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13

Hirner, Joshua J., and Michael J. Zacuto. "7-Chloroquinoline: a versatile intermediate for the synthesis of 7-substituted quinolines." Tetrahedron Letters 50, no. 35 (2009): 4989–93. http://dx.doi.org/10.1016/j.tetlet.2009.06.077.

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14

Gomes, Ligia R., John Nicolson Low, James L. Wardell, Laura N. de F. Cardoso та Marcus V. N. De Souza. "Substituted 4-alkoxy-7-Cl-quinolines exhibiting π–π stacking". Acta Crystallographica Section C Crystal Structure Communications 69, № 2 (2013): 191–94. http://dx.doi.org/10.1107/s0108270113001510.

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The molecules of 4-allyloxy-7-chloroquinoline, C12H10ClNO, (I), 7-chloro-4-methoxyquinoline, C10H8ClNO, (II), and 7-chloro-4-ethoxyquinoline, C11H10ClNO, (III), are all planar. In all three structures, π–π interactions between the quinoline ring systems are generated by unit-cell translations along theaaxes, irrespective of space group. These structures are the first reported for 4-alkoxyquinolines.

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15

Yanni, A. S., and Z. H. Khalil. "Synthesis of some new 7-substituted aminomethyl-6-chloroquinoline-5,8-quinones." Journal of Chemical Technology & Biotechnology 51, no. 1 (2007): 67–70. http://dx.doi.org/10.1002/jctb.280510107.

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16

Raj, Raghu, Vishu Mehra, Jiri Gut, et al. "Discovery of highly selective 7-chloroquinoline-thiohydantoins with potent antimalarial activity." European Journal of Medicinal Chemistry 84 (September 2014): 425–32. http://dx.doi.org/10.1016/j.ejmech.2014.07.048.

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17

Kim, Chun-Hyung, Pierre Leblanc, and Kwang-Soo Kim. "4-amino-7-chloroquinoline derivatives for treating Parkinson’s disease: implications for drug discovery." Expert Opinion on Drug Discovery 11, no. 4 (2016): 337–41. http://dx.doi.org/10.1517/17460441.2016.1154529.

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18

YANNI, A. S., and Z. H. KHALIL. "ChemInform Abstract: Synthesis of Some New 7-Substituted Aminomethyl-6-chloroquinoline-5,8- quinones." ChemInform 22, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199144193.

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19

YANNI, A. S., and Z. H. KHALIL. "ChemInform Abstract: Synthesis of Some New 7-Substituted Aminomethyl-6-chloroquinoline-5,8- quinones." ChemInform 22, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199127179.

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20

Shalini, Matt D. Johansen, Laurent Kremer, and Vipan Kumar. "Variedly connected 1,8-naphthalimide-7-chloroquinoline conjugates: Synthesis, anti-mycobacterial and cytotoxic evaluation." Bioorganic Chemistry 92 (November 2019): 103241. http://dx.doi.org/10.1016/j.bioorg.2019.103241.

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21

Shalini, Albertus Viljoen, Laurent Kremer, and Vipan Kumar. "Alkylated/aminated nitroimidazoles and nitroimidazole-7-chloroquinoline conjugates: Synthesis and anti-mycobacterial evaluation." Bioorganic & Medicinal Chemistry Letters 28, no. 8 (2018): 1309–12. http://dx.doi.org/10.1016/j.bmcl.2018.03.021.

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22

Coghi, Paolo, Jerome P. L. Ng, Ali Adnan Nasim, and Vincent Kam Wai Wong. "N-[7-Chloro-4-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]quinoline]-acetamide." Molbank 2021, no. 2 (2021): M1213. http://dx.doi.org/10.3390/m1213.

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The 1,2,3-triazole is a well-known biologically active pharmacophore constructed by the copper-catalyzed azide–alkyne cycloaddition. We herein reported the synthesis of 4-amino-7-chloro-based [1,2,3]-triazole hybrids via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of 4-azido-7-chloroquinoline with an alkyne derivative of acetaminophen. The compound was fully characterized by Fourier-transform infrared (FTIR), proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV) and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro with different normal and cancer cell lines. The drug likeness of the compound was also investigated by predicting its pharmacokinetic properties.

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23

Singh, Pardeep, Raghu Raj, Parvesh Singh, Jiri Gut, Philip J. Rosenthal та Vipan Kumar. "Urea/oxalamide tethered β-lactam-7-chloroquinoline conjugates: Synthesis and in vitro antimalarial evaluation". European Journal of Medicinal Chemistry 71 (січень 2014): 128–34. http://dx.doi.org/10.1016/j.ejmech.2013.10.079.

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24

Begnini, Karine Rech, Wladimir R. Duarte, Liziane Pereira da Silva, et al. "Apoptosis induction by 7-chloroquinoline-1,2,3-triazoyl carboxamides in triple negative breast cancer cells." Biomedicine & Pharmacotherapy 91 (July 2017): 510–16. http://dx.doi.org/10.1016/j.biopha.2017.04.098.

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25

Šegan, Sandra, Igor Opsenica, Mario Zlatović, Dušanka Milojković-Opsenica, and Bogdan Šolaja. "Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds." Journal of Chromatography B 1012-1013 (February 2016): 144–52. http://dx.doi.org/10.1016/j.jchromb.2016.01.033.

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26

Singh, Amandeep, Albertus Viljoen, Laurent Kremer, and Vipan Kumar. "Synthesis and Antimycobacterial Evaluation of Piperazyl-alkyl-Ether Linked 7-Chloroquinoline-Chalcone/Ferrocenyl Chalcone Conjugates." ChemistrySelect 3, no. 29 (2018): 8511–13. http://dx.doi.org/10.1002/slct.201801453.

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27

YANNI, A. S., Z. H. KHALIL, and A. A. TIMMAWY. "ChemInform Abstract: Synthesis of Some New Sulfonamide Derivatives of 7-Chloroquinoline-5,8- dione and Pyridocarbazolediones." ChemInform 22, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199140154.

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28

Parthiban, A., J. Muthukumaran, Ashan Manhas, Kumkum Srivastava, R. Krishna, and H. Surya Prakash Rao. "Synthesis, in vitro and in silico antimalarial activity of 7-chloroquinoline and 4H-chromene conjugates." Bioorganic & Medicinal Chemistry Letters 25, no. 20 (2015): 4657–63. http://dx.doi.org/10.1016/j.bmcl.2015.08.030.

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29

Sonego, Mariana S., Natália V. Segatto, Lucas Damé, et al. "7-Chloroquinoline-1,2,3-triazoyl carboxamides induce cell cycle arrest and apoptosis in human bladder carcinoma cells." Investigational New Drugs 38, no. 4 (2019): 1020–30. http://dx.doi.org/10.1007/s10637-019-00861-w.

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30

Reis, Angélica S., Mikaela Pinz, Luis Fernando B. Duarte, et al. "4-phenylselenyl-7-chloroquinoline, a novel multitarget compound with anxiolytic activity: Contribution of the glutamatergic system." Journal of Psychiatric Research 84 (January 2017): 191–99. http://dx.doi.org/10.1016/j.jpsychires.2016.10.007.

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31

Silva, Vanessa D. G., Angélica S. Reis, Mikaela P. Pinz, et al. "Further analysis of acute antinociceptive and anti-inflammatory actions of 4-phenylselenyl-7-chloroquinoline in mice." Fundamental & Clinical Pharmacology 31, no. 5 (2017): 513–25. http://dx.doi.org/10.1111/fcp.12295.

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32

da Costa Rodrigues, Karline, Cristiani Folharini Bortolatto, Renata Leivas de Oliveira, et al. "4-Phenylselanyl-7-chloroquinoline attenuates hepatic injury triggered by neonatal exposure to monosodium glutamate in rats." Life Sciences 280 (September 2021): 119751. http://dx.doi.org/10.1016/j.lfs.2021.119751.

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33

Đức, Lê Trọng, Nguyễn Tiến Công та Nguyễn Quang Tùng. "Tổng hợp và xác định cấu trúc một số hợp chất 4-(2-arylidenehydrazinyl)-7-chloroquinoline". Tạp chí Khoa học 14, № 3 (2019): 5. http://dx.doi.org/10.54607/hcmue.js.14.3.2133(2017).

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7-Chloro-4-hydrazinylquinoline and seven hydrazone derivatives were synthesized from 4,7-dichloroquinoline. The structures of the compounds were determined by IR, 1H-NMR, 13C-NMR and HR-MS spectral data

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34

Abdi, Bayan, Mona Fekadu, Digafie Zeleke, Rajalakshmanan Eswaramoorthy, and Yadessa Melaku. "Synthesis and Evaluation of the Antibacterial and Antioxidant Activities of Some Novel Chloroquinoline Analogs." Journal of Chemistry 2021 (December 30, 2021): 1–13. http://dx.doi.org/10.1155/2021/2408006.

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Quinoline heterocycle is a useful scaffold to develop bioactive molecules used as anticancer, antimalaria, and antimicrobials. Inspired by their numerous biological activities, an attempt was made to synthesize a series of novel 7-chloroquinoline derivatives, including 2,7-dichloroquinoline-3-carbonitrile (5), 2,7-dichloroquinoline-3-carboxamide (6), 7-chloro-2-methoxyquinoline-3-carbaldehyde (7), 7-chloro-2-ethoxyquinoline-3-carbaldehyde (8), and 2-chloroquinoline-3-carbonitrile (12) by the application of Vilsmeier–Haack reaction and aromatic nucleophilic substitution of 2,7-dichloroquinoline-3-carbaldehyde. The carbaldehyde functional group was transformed into nitriles using POCl3 and NaN3, which was subsequently converted to amide using CH3CO2H and H2SO4. The compounds synthesized were screened for their antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Streptococcus pyogenes. Compounds 6 and 8 showed good activity against E. coli with an inhibition zone of 11.00 ± 0.04 and 12.00 ± 0.00 mm, respectively. Compound 5 had good activity against S. aureus and P. aeruginosa with an inhibition zone of 11.00 ± 0.03 mm relative to standard amoxicillin (18 ± 0.00 mm). Compound 7 displayed good activity against S. pyogenes with an inhibition zone of 11.00 ± 0.02 mm. The radical scavenging activity of these compounds was evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH), and compounds 5 and 6 displayed the strongest antioxidant activity with IC50 of 2.17 and 0.31 µg/mL relative to ascorbic acid (2.41 µg/mL), respectively. The molecular docking study of the synthesized compounds was conducted to investigate their binding pattern with topoisomerase IIβ and E. coli DNA gyrase B. Compounds 6 (−6.4 kcal/mol) and 8 (−6.6 kcal/mol) exhibited better binding affinity in their in silico molecular docking against E. coli DNA gyrase. The synthesized compounds were also found to have minimum binding energy ranging from −6.9 to −7.3 kcal/mol against topoisomerase IIβ. The SwissADME predicted results showed that the synthesized compounds 5–8 and 12 satisfy Lipinski’s rule of five with zero violations. The ProTox-II predicted organ toxicity results revealed that all the synthesized compounds were inactive in hepatotoxicity, immunotoxicity, mutagenicity, and cytotoxicity. The findings of the in vitro antibacterial and molecular docking analysis suggested that compound 8 might be considered a hit compound for further analysis as antibacterial and anticancer drug. The radical scavenging activity displayed by compounds 5 and 6 suggests these compounds as a radical scavenger.

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35

Yun, Xiaoyun, Yuhan Xie, Jerome P. L. Ng, Betty Yuen Kwan Law, Vincent Kam Wai Wong, and Paolo Coghi. "2-Bromo-3-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)-methoxy)-benzaldehyde." Molbank 2022, no. 1 (2022): M1351. http://dx.doi.org/10.3390/m1351.

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The 1,2,3-triazole ring system can be easily obtained by copper-catalyzed click reaction of azides with alkynes. 1,2,3-Triazole exhibits a myriad of biological activities, including antimalarial, antibacterial, and antiviral activities. We herein reported the synthesis of quinoline-based [1,2,3]-triazole hybrid via Cu(I)-catalyzed click reaction of 4-azido-7-chloroquinoline with alkyne derivative of 2-bromobenzaldehyde. The compound was fully characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV), and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro against two different normal cell lines. Preliminary studies attempted to evaluate its interaction with Delta RBD of spike protein of SARS-CoV-2 by bio-layer interferometry. Finally, the drug-likeness of the compound was also investigated by predicting its pharmacokinetic properties.

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36

Aboelnaga, Asmaa, and Taghreed H. EL-Sayed. "Click synthesis of new 7-chloroquinoline derivatives by using ultrasound irradiation and evaluation of their biological activity." Green Chemistry Letters and Reviews 11, no. 3 (2018): 254–63. http://dx.doi.org/10.1080/17518253.2018.1473505.

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37

Wadi, Ishan, Davinder Prasad, Neha Batra, et al. "Targeting Asexual and Sexual Blood Stages of the Human Malaria ParasiteP. falciparumwith 7‐Chloroquinoline‐Based 1,2,3‐Triazoles." ChemMedChem 14, no. 4 (2019): 484–93. http://dx.doi.org/10.1002/cmdc.201800728.

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38

Pinz, Mikaela, Angélica S. Reis, Vanessa Duarte, et al. "4-Phenylselenyl-7-chloroquinoline, a new quinoline derivative containing selenium, has potential antinociceptive and anti-inflammatory actions." European Journal of Pharmacology 780 (June 2016): 122–28. http://dx.doi.org/10.1016/j.ejphar.2016.03.039.

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39

Wilhelm, Ethel A., Niége C. Machado, Andrieli B. Pedroso, et al. "Organocatalytic synthesis and evaluation of 7-chloroquinoline-1,2,3-triazoyl carboxamides as potential antinociceptive, anti-inflammatory and anticonvulsant agent." RSC Adv. 4, no. 78 (2014): 41437–45. http://dx.doi.org/10.1039/c4ra07002j.

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40

Burnett, James C., Dejan Opsenica, Kamaraj Sriraghavan, et al. "A Refined Pharmacophore Identifies Potent 4-Amino-7-chloroquinoline-Based Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease." Journal of Medicinal Chemistry 50, no. 9 (2007): 2127–36. http://dx.doi.org/10.1021/jm061446e.

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41

da Silva Caleffi, Guilherme, João Paulo Gomes de Oliveira, Everton da Paz Silva, et al. "Synthesis and structural characterization by NMR and X-ray of new Morita-Baylis-Hillman adducts derived from 7-chloroquinoline." Journal of Molecular Structure 1133 (April 2017): 358–68. http://dx.doi.org/10.1016/j.molstruc.2016.12.022.

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42

Raj, Raghu, Pardeep Singh, Parvesh Singh, Jiri Gut, Philip J. Rosenthal, and Vipan Kumar. "Azide-alkyne cycloaddition en route to 1 H -1,2,3-triazole-tethered 7-chloroquinoline-isatin chimeras: Synthesis and antimalarial evaluation." European Journal of Medicinal Chemistry 62 (April 2013): 590–96. http://dx.doi.org/10.1016/j.ejmech.2013.01.032.

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Freier, C., G. Alberici, P. Turk, F. Baud, and C. Bohuon. "A radioimmunoassay for the antimalarial drug chloroquine." Clinical Chemistry 32, no. 9 (1986): 1742–45. http://dx.doi.org/10.1093/clinchem/32.9.1742.

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Abstract We describe a 3H-based RIA for the antimalarial drug chloroquine (CLQ), the most commonly used antimalarial drug. In the assay a monoclonal antibody is used that is directed against 4-amino-7-chloroquinoline conjugated to keyhole limpet hemocyanin by the glutaraldehyde method. Besides CLQ, this antibody also recognizes with good affinity the 4-aminoquinoline homologs, hydroxychloroquine and amodiaquine. No extraction step or sample preparation is required, and the method can detect as little as 10 micrograms/L, the lower concentration in plasma of humans who are taking CLQ as a preventive measure. The between-assay CV is less than or equal to 10%, the within-assay CV less than or equal to 3%. Results correlate with those by liquid chromatography (r2 = 0.96). The speed and simplicity of the RIA method make it useful in evaluating the CLQ concentrations in acutely toxic patients.

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Wilhelm, Ethel A., Niege C. Machado, Andrieli B. Pedroso, et al. "ChemInform Abstract: Organocatalytic Synthesis and Evaluation of 7-Chloroquinoline-1,2,3-triazoyl Carboxamides as Potential Antinociceptive, Anti-inflammatory and Anticonvulsant Agent." ChemInform 46, no. 12 (2015): no. http://dx.doi.org/10.1002/chin.201512220.

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Singh, Pardeep, Parvesh Singh, Malkeet Kumar та ін. "Synthesis, docking and in vitro antimalarial evaluation of bifunctional hybrids derived from β-lactams and 7-chloroquinoline using click chemistry". Bioorganic & Medicinal Chemistry Letters 22, № 1 (2012): 57–61. http://dx.doi.org/10.1016/j.bmcl.2011.11.082.

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Lad, Chaitali, Ishan Panchal, Ashish Patel, et al. "In silico analysis, synthesis and biological evaluation of DHFR inhibitors." Folia Medica 63, no. 5 (2021): 745–59. http://dx.doi.org/10.3897/folmed.63.e56786.

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Introduction: Malaria is one of the varieties of fatal diseases caused by a protozoan parasite that is now considered to be the greatest global health challenge. A parasite of Plasmodium species triggers it transmitting the disease to humans by the bites of female Anopheles mosquitoes. Aim: To screen out designed molecules by molecular docking analysis and assess their pharmacokinetic properties using SwissADME. To synthesize the designed compounds. To characterize the synthesized compounds by TLC, melting point, IR spectroscopy, mass spectrometry, 1H NMR, and 13C NMR. To evaluate the synthesized compounds for antimalarial activity. Materials and methods: In silico analysis was performed with SWISSADME, and molecular docking was performed by AutoDock Vina version 4.2. In vitro antimalarial activity study was performed. Results: In-vitro studies of synthesized molecules showed that compounds C2 (IC50 1.23), C6 (IC50 0.48), C10 (IC50 0.79), and C14 (IC50&nbsp;0.19) possess good antimalarial activity. Conclusions: 7-chloroquinoline-piperazine derivatives exhibited potential antimalarial compounds for pf-DHFR inhibitors.

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Montoya, Alba, Jairo Quiroga, Rodrigo Abonia, Manuel Nogueras, Justo Cobo, and Braulio Insuasty. "Synthesis and in Vitro Antitumor Activity of a Novel Series of 2-Pyrazoline Derivatives Bearing the 4-Aryloxy-7-chloroquinoline Fragment." Molecules 19, no. 11 (2014): 18656–75. http://dx.doi.org/10.3390/molecules191118656.

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Papadopoulou, M. V., M. Ji, M. K. Rao, and W. D. Bloomer. "4-[3-(2-Nitro-1-imidazolyl)propylamino]-7-chloroquinoline Hydrochloride (NLCQ-1), a Novel Bioreductive Compound as a Hypoxia-Selective Cytotoxin." Oncology Research Featuring Preclinical and Clinical Cancer Therapeutics 12, no. 4 (2001): 185–92. http://dx.doi.org/10.3727/096504001108747675.

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Bhat, Balkrishen, and A. P. Bhaduri. "Grignard Reaction of 2-Substituted-3-Cyanoquinolines." Zeitschrift für Naturforschung B 40, no. 7 (1985): 990–95. http://dx.doi.org/10.1515/znb-1985-0724.

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Abstract Grignard reactions of 2-morpholino and 2-methylthio-3-cyanoquinoline, 2-chloro-3-cyanoquinoline, 2-chloro-3-cyano-6-methoxyquinoline and 2-chloro-3-cyano-7-methylquinoline with alkyl or aryl magnesium halides have been studied. It was found that 2-morpholino and 2-methylthio- 3-cyanoquinolines gave 1,4-addition products followed by rapid aromatisation. 2-Chloro-3- cyanoquinoline with alkyl magnesium halides furnished 1,4-addition products but with aryl magnesium halides 1,4- and 1,2-addition products were obtained. The cyano group of 4-aryl-2-chloro- 3-cyano-1,4-dihydroquinolines was found to participate in the Grignard reaction to yield 1,2- addition products. 2-Chloro-3-cyano-6-m ethoxyquinoline with alkyl and phenyl magnesium halides yielded exclusively 1,4-addition products. Similarly with p-m ethoxyphenyl magnesium bromide, 1,4-addition products were isolated which participated in the Grignard reaction to yield the expected adducts. Unlike the other chloroquinoline derivatives, 2-chloro-3-cyano-7-methylquinoline with alkyl magnesium halide formed 1 ,2-addition products but with aryl magnesium halides, 1,4-addition products were isolated. The 4-alkyl-2-chloro-3-cyano-l,4-dihydroquinolines were unstable as compared to their 4-aryl analogs. A couple of the Grignard reaction products were found to be unstable on activated surface.

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Westphal, Regina, Jorge Welton de Souza Pina, Juliana Panceri Franco, et al. "Synthesis and Evaluation of Corrosion Inhibiting Activity of New Molecular Hybrids Containing the Morpholine, 1,4-Naphthoquinone, 7-Chloroquinoline and 1,3,5-Triazine Cores." Advances in Chemical Engineering and Science 10, no. 04 (2020): 378–98. http://dx.doi.org/10.4236/aces.2020.104024.

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