Ionic Liquid-Promoted Synthesis of Novel Chromone-Pyrimidine Coupled Derivatives, Antimicrobial Analysis, Enzyme Assay, Docking Study and Toxicity Study

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Shailee V TiwariAnna Pratima G Nikalje

Abstract

Herein, we report an environmentally friendly, rapid, and convenient ionic liquid ([Et₃NH][HSO₄])-promoted facile synthesis of ethyl 4-(6-substituted-4-oxo-4H-chromen-3-yl)-6-methyl-2-thioxo/oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives 4(a-f) and 4-(6-substituted-4-oxo-4H-chromen-3-yl)-6-methyl-2-thioxo/oxo-1,2,3,4-tetrahydropyrimidine-5- carbohydrazide derivatives 6(a-f). All the synthesized derivatives 4(a-f) and 6(a-f) were evaluated for their in vitro antifungal and antibacterial activity, by method recommended by National Committee for Clinical Laboratory Standards (NCCLS). The compound 6c bearing a fluoro group on the chromone ring and oxygen and a hydrazino group (-NHNH₂) on the pyrimidine ring, was found to be the most potent antibacterial compound amongst the synthesized derivatives. The compound 6f bearing a methoxy group (-OCH₃) on the chromone ring and sulphur group on the pyrimidine ring, was found to exhibit equipotent antifungal activity when compared with the standard drug miconazole. A D-alanine-D-alanine ligase (DdlB) enzyme assay study and an ergosterol extraction and quantitation assay study were performed to predict the mode of action of the synthesized compounds. A molecular docking study was...Continue Reading

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Citations

Jul 2, 2020·Journal of Biomolecular Structure & Dynamics·Kshipra S KarnikPravin S Wakte
Aug 25, 2020·Pharmaceutical Chemistry Journal·Noor Ul Amin MohsinUsman Saleem
Mar 11, 2021·Bioorganic & Medicinal Chemistry Letters·Aniket P SarkateShashikant V Bhandari
Jul 27, 2021·Russian Chemical Bulletin = Izvestii︠a︡ Akademii Nauk. Serii︠a︡ Khimicheskai︠a︡·S S ShatokhinÉ T Oganesyan

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Methods Mentioned

BETA
Assay
enzyme

Software Mentioned

Qikprop
SITEMAP
OPLS
PRIME
Ligprep
Maestro
PROCHECK
WHATIF
blast
SSpro

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