Synthesis and antibacterial activity of isothiazolyl oxazolidinones and analogous 3(2H)-isothiazolones.
The synthesis and antibacterial activity of several new 5-((3-oxoisothiazol-2(3H)-yl)methyl)-3-phenyloxazolidin-2-ones 8 and analogous 2-(4-substituted phenyl)-3(2H)-isothiazolones 3 and 4 substituted at 4 and/or 3-positions of the phenyl moiety with different groups of which some have shown to increase the antibacterial activity of both 3-aryl-2-oxazolidinones and 3(2H)-isothiazolones is described. The most active compounds were isothiazolyl oxazolidinones 8a,j with unsubstituted and 8b with 4-F substituted phenyl rings which showed activities higher than analogous 3(2H)-isothiazolones and comparable or superior to linezolid, vancomycin, and ciprofloxacin against some tested microorganisms. The change in position of F and/or the use of larger substituents gave compounds with reduced or no activity. Evaluation of cytotoxicity to mouse fibroblast (NIH/3T3) cells indicated that these compounds exhibit antibacterial activity at non-cytotoxic concentrations.
Adibpour
Neda
N
Department of Medicinal Chemistry, School of Pharmacy, Ahwaz Jundishapur University of Medical Sciences, Ahwaz, Iran. n.adibpour@ajums.ac.ir
Khalaj
Ali
A
Rajabalian
Saeed
S
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D001419:Bacteria / Q000187:drug effects; D051379:Mice; D008826:Microbial Sensitivity Tests; D041681:NIH 3T3 Cells; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity
D000900:Anti-Bacterial Agents; D023303:Oxazolidinones; D013844:Thiazoles