Premium
Fluorinated hydrazonoyl chlorides as precursors for synthesis of antimicrobial azoles
Author(s) -
AlHussain Sami A.,
Alshehrei Fatimah,
Zaki Magdi E. A.,
Harras Marwa F.,
Farghaly Thoraya A.,
Muhammad Zeinab A.
Publication year - 2021
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4198
Subject(s) - chemistry , dna gyrase , docking (animal) , thiazole , antimicrobial , pyrazole , combinatorial chemistry , stereochemistry , active site , candida albicans , reagent , enzyme , escherichia coli , organic chemistry , biochemistry , microbiology and biotechnology , medicine , nursing , biology , gene
Hydrazonoyl halides have been known for their ability to react with different reagents to afford wide range of bioactive heterocyclic systems as thiazoles and imidazopyrazoles. This research work focused on the synthesis of two new fluorinated hydrazonoyl chlorides and used them in synthesis of novel series of thiazole derivatives and two imidazopyrazole systems. The mechanistic pathways and the structures of all synthesized derivatives were discussed and assured based on the available spectral data. The results of antimicrobial activity of the tested thiazoles and imidazopyrazoles showed that some derivatives have moderate to no activity against tested fungi and bacteria strains. Only one derivative namely 2‐(2‐(3‐fluoro‐4‐methylphenyl)hydrazono)‐7‐(2‐oxoindolin‐3‐ylidene)‐2,7‐dihydro‐3 H ‐imidazo[1,2‐ b ]pyrazole‐3,6(5 H )‐dione is the most active against Candida albicans ( CA ) with IZD = 20 mm, which was equipotent to ketoconazole. Furthermore, docking simulation was carried out to predict the binding pattern of the new compounds in the ATP binding site of the DNA gyrase B enzyme. The results of the docking simulation revealed that compounds 9a‐e , 12 , and 13a,b fit well in the ATP binding site of DNA gyrase B with docking score values ranging from −5.883 to −6.833 kcal/mol.