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1,3‐Benzothiazoles as Antimicrobial Agents
Author(s) -
Defrenza Ivana,
Catalano Alessia,
Carocci Alessia,
Carrieri Antonio,
Muraglia Marilena,
Rosato Antonio,
Corbo Filomena,
Franchini Carlo
Publication year - 2015
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.2222
Subject(s) - chemistry , moiety , substituent , antifungal , candida albicans , benzothiazole , stereochemistry , antimicrobial , candida tropicalis , aryl , antibacterial activity , combinatorial chemistry , in vitro , bacteria , organic chemistry , yeast , biochemistry , microbiology and biotechnology , alkyl , genetics , biology
Starting from 2‐amino‐1,3‐mercaptobenzothiazoles recently reported ( 1a , 1b , 1c , 1d , 1e , 1f , 1g , 1h ), a series of the corresponding 2‐mercapto‐1,3‐benzothiazole isosters ( 2a , 2b , 2c , 2d , 2e , 2f , 2g , 2h ) were screened for their in vitro antibacterial and antifungal activities. Results underline that the presence of the mercapto moiety at the 2‐position of the heterocyclic nucleus is crucial for activity against bacteria. The biological screening against Candida spp. identified commercial 2f as the most promising compound as antifungal against Candida albicans and tropicalis . Molecular modeling studies supported these results. Then, to enlarge structure‐activity relationship (SAR) studies on series 1 , newly synthesized compounds ( 1k , 1l , 1m , 1n , 1o , 1p ) were reported. All the compounds belonging to this series and bearing a bulky substituent at the 6‐position of the aryl moiety showed high antifungal activity.