These authors contributed equally to this work.
Design, Synthesis, and in vitro Antibacterial Activity of Fluoroquinolone Derivatives Containing a Chiral 3-(Alkoxyimino)-2-(aminomethyl)azetidine Moiety
Article first published online: 25 MAY 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Volume 7, Issue 7, pages 1230–1236, July 2012
How to Cite
Lv, K., Sun, Y., Sun, L., Wei, Z., Guo, H., Wu, J. and Liu, M. (2012), Design, Synthesis, and in vitro Antibacterial Activity of Fluoroquinolone Derivatives Containing a Chiral 3-(Alkoxyimino)-2-(aminomethyl)azetidine Moiety. ChemMedChem, 7: 1230–1236. doi: 10.1002/cmdc.201200210
- Issue published online: 25 JUN 2012
- Article first published online: 25 MAY 2012
- Manuscript Revised: 10 MAY 2012
- Manuscript Received: 20 APR 2012
- National S&T Major Special Project. Grant Number: 2012ZX09301002-001-017
- drug design;
- medicinal chemistry;
A series of novel (R)/(S)-7-(3-alkoxyimino-2-aminomethyl-1-azetidinyl)fluoroquinolone derivatives were synthesized and evaluated for their in vitro antibacterial activity against representative strains. Our results reveal that 12 of the target compounds generally show better activity (MIC: <0.008–0.5 μg mL−1) against the tested Gram-positive strains including MRSA and MRSE than levofloxacin (LVFX, MIC: 0.125–8 μg mL−1). Their activity is similar to that of gemifloxacin (GMFX, MIC: <0.008–4 μg mL−1). However, they are generally less active than the two reference drugs against Gram-negative strains. Moreover, against clinical strains of S. aureus including MRSA and S. epidermidis including MRSE, the MIC50 values (0.06–16 μg mL−1) and MIC90 values (0.5–32 μg mL−1) of compounds 16 w, y, and z are 2–8- and 2–16-fold less than LVFX, respectively, and 16 w (MIC90 range: 0.5–4 μg mL−1) was also found to be more active than GMFX (MIC90 range: 1–8 μg mL−1).