title: Synthesis, antimycobacterial and antibacterial activity of ciprofloxacin derivatives containing a N-substituted benzyl moiety.
abstract: We report herein the design and synthesis of a series of novel ciprofloxacin (CPFX) derivatives with remarkable improvement in lipophilicity by introducing a substituted benzyl moiety to the N atom on the C-7 piperazine ring of CPFX. Antimycobacterial and antibacterial activity of the newly synthesized compounds was evaluated. Results reveal that compound 4f has good in vitro activity against all of the tested Gram-positive strains including MRSA and MRSE (MICs: 0.06-32 μg/mL) which is two to eightfold more potent than or comparable to the parent drug CPFX (MICs: 0.25-128 μg/mL), Gram-negative bacteria P. aeruginosa (MICs: 0.5-4 μg/mL) and M. tuberculosis H37Rv ATCC 27294 (MIC: 1 μg/mL).
authors.affiliation: Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, PR China.
authors.forename: Shuo
authors.initials: S
authors.lastname: Wang
authors.forename: Xue-Dong
authors.initials: XD
authors.lastname: Jia
authors.forename: Ming-Liang
authors.initials: ML
authors.lastname: Liu
authors.forename: Yu
authors.initials: Y
authors.lastname: Lu
authors.forename: Hui-Yuan
authors.initials: HY
authors.lastname: Guo
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001593:Benzyl Compounds / Q000737:chemistry*; D002939:Ciprofloxacin / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D006090:Gram-Negative Bacteria / Q000187:drug effects* / Q000254:growth & development; D006094:Gram-Positive Bacteria / Q000187:drug effects* / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D001593:Benzyl Compounds; D002939:Ciprofloxacin