首页|Synthesis and biological activity of 2-[2-(7-chloroquinolin-4-ylthio)-4-methylthiazol-5-yl]-N-phenylacetamide derivatives as antimalarial and cytotoxic agents

Synthesis and biological activity of 2-[2-(7-chloroquinolin-4-ylthio)-4-methylthiazol-5-yl]-N-phenylacetamide derivatives as antimalarial and cytotoxic agents

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A novel series of 2-[2-(7-chloroquinolin-4-ylthio)-4-methylthiazol-5-yl]-N-phenylacetamide derivatives is synthesized via substitution with 2-mercapto-4-methyl-5-thiazoleacetic acid at position 4 of 4,7-dichloroquinoline to obtain an intermediate acetic acid derivative. The chemical behavior of these reactants was investigated using different reaction conditions to optimize the nucleophilic substitution at position 4. The final compounds are prepared using a modified version of the Steglich esterification reaction between the acetic acid intermediate 3 and different anilines. The structures are confirmed by infrared, 1H, 13C, distortionless enhancement by polarization transfer 135 degrees, Correlated Spectroscopy, heteronuclear correlation spectroscopy and (Long range HETCOR using three BIRD pulses) FLOCK-NMR spectral studies, and by elemental analysis. The synthesized compounds are tested in vitro and in vivo for their potential antimalarial and anticancer activities, with derivative 11 being the most promising candidate.

anticancerantimalarialPlasmodiumquinolinethiazoleacetic acid

Ramirez, Hegira、Rodrigues, Juan R.、Mijares, Michael R.、De Sanctis, Juan B.、Charris, Jaime E.

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Cent Univ Venezuela, Fac Pharm, Organ Synth Lab, 47206 Los Chaguaramos, Caracas 1041, Venezuela

Univ Simon Bolivar, Dept Cell Biol, Lab Pharmacol & Toxicol, Caracas, Venezuela

Cent Univ Venezuela, Fac Pharm, Biotechnol Unit, Caracas, Venezuela

Cent Univ Venezuela, Fac Med, Inst Immunol, Caracas, Venezuela

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2020

10.1177/1747519819899073

Journal of chemical research.

Journal of chemical research.

ISSN：1747-5198
年,卷(期)：2020.44(5/6)
  • 6
  • 36