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Design, Synthesis, and in vitro Antibacterial Activity of Fluoroquinolone Derivatives Containing a Chiral 3‐(Alkoxyimino)‐2‐(aminomethyl)azetidine Moiety
Author(s) -
Lv Kai,
Sun Yexin,
Sun Lanyin,
Wei Zengquan,
Guo Huiyuan,
Wu Jinwei,
Liu Mingliang
Publication year - 2012
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201200210
Subject(s) - levofloxacin , antibacterial activity , gemifloxacin , chemistry , in vitro , minimum inhibitory concentration , stereochemistry , antibiotics , bacteria , biology , biochemistry , genetics
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 MIC 50 values (0.06–16 μg mL −1 ) and MIC 90 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 (MIC 90 range: 0.5–4 μg mL −1 ) was also found to be more active than GMFX (MIC 90 range: 1–8 μg mL −1 ).