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Synthesis and Antimicrobial Activity of Methyl 2‐(2‐(2‐Arylquinazolin‐4‐yl)sulfanyl)acetylamino Alkanoates
Author(s) -
Megahed M. I.,
Fathalla W.
Publication year - 2018
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.3348
Subject(s) - chemistry , sulfanyl , candida albicans , antimicrobial , antibacterial activity , hydrochloride , escherichia coli , yeast , bacteria , novobiocin , stereochemistry , organic chemistry , microbiology and biotechnology , antibiotics , biochemistry , genetics , gene , biology
A series of methyl 2‐(2‐(2‐arylquinazolin‐4‐yl)sulfanyl)acetylamino alkanoates have been developed on the basis of the S ‐chemoselective reaction of 2‐arylquinazolin‐4(3 H )‐thione with ethyl chloroacetate and N , N′ ‐dicyclohexylcarbodiimide coupling method with amino acid ester hydrochloride. The precursor 2‐arylquinazolin‐4(3 H )‐thione was prepared by a new thiation method from 2‐arylquinazolin‐4(3 H )‐one by a two‐step reaction that includes chlorination and then the reaction with N ‐cyclohexyldithiocarbamate cyclohexyl ammonium salt. The antimicrobial activity of the synthesized compounds was tested in vitro via paper‐disc agar‐plate method against two bacterial strains Gram‐positive bacteria Staphylococcus aureus and Gram‐negative bacteria Escherichia coli and a pathogenic yeast Candida albicans . Most synthesized compounds showed remarkable antibacterial activity against E . coli overpassing the standard reference antibiotics applied: tetracycline, erythromycin, and novobiocin. On the other hand, most synthesized compounds gave moderate antifungal activity against pathogenic yeast C . albicans .