Effects of positional and geometrical isomerism on the biological activity of some novel oxazolidinones.
Some novel oxazolidinone derivatives with benzotriazole as pendant have been synthesized and tested for antibacterial activity. Linearly attached benzotriazole derivative showed more potency compared to angular one in vitro. Out of E/Z-isomers of angularly attached derivatives E-isomer was found to be more potent than Z-isomer. Either less active or inactive molecules were obtained, when benzotriazole was replaced with benzimidazole, benzthiazole, or benzoxazole. Finally, thioacetamide analogue of linear compound gave a lead having activity similar to linezolid in vitro.
Das
Jagattaran
J
Discovery Research, Dr. Reddy's Laboratories Ltd, Miyapur, Hyderabad 500 049, India. jagat@drreddys.com
Rao
C V Laxman
CV
Sastry
T V R S
TV
Roshaiah
M
M
Sankar
P Gowri
PG
Khadeer
Abdul
A
Kumar
M Sitaram
MS
Mallik
Arundhuti
A
Selvakumar
N
N
Iqbal
Javed
J
Trehan
Sanjay
S
D000081:Acetamides; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001562:Benzimidazoles / Q000737:chemistry / Q000494:pharmacology; D001583:Benzoxazoles / Q000737:chemistry / Q000494:pharmacology; D007536:Isomerism; D000069349:Linezolid; D008826:Microbial Sensitivity Tests; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013853:Thioacetamide / Q000737:chemistry / Q000494:pharmacology; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000081:Acetamides; D000890:Anti-Infective Agents; D001562:Benzimidazoles; D001583:Benzoxazoles; D023303:Oxazolidinones; D014230:Triazoles; D013853:Thioacetamide; C012771:benzotriazole; C031000:benzimidazole; D000069349:Linezolid