Chiral DNA gyrase inhibitors. 2. Asymmetric synthesis and biological activity of the enantiomers of 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2, 3-dihydro-7H …

LA Mitscher, PN Sharma, DTW Chu…

Index: Mitscher; Sharma; Chu; Shen; Pernet Journal of Medicinal Chemistry, 1987 ,  vol. 30,  # 12  p. 2283 - 2286

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Citation Number: 103

Abstract

A short and efficient synthesis, starting with (R)-and (S)-alaninol, of the two optical antipodes of the quinolone antimicrobial agent ofloxacin has been devised. Testing in vitro of the products against a range of bacteria and in an assay system incorporating purified DNA gyrase from different bacterial species demonstrates that the S-(-) enantiomer is substantially the more active.

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ethyl (R)-(+)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate Structure

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