title: Part IV: Design, synthesis and antitumor activity of fluoroquinolone C-3 heterocycles: bis-oxadiazole methylsulfide derivatives derived from ciprofloxacin.
abstract: To explore an efficient strategy for further development of anticancer fluoroquinolone candidates derived from ciprofloxacin, a heterocyclic ring as the bioisosteric replacement of C3 carboxyl group led to a key intermediate, oxadiazole thiol (5), which was further modified to the bis-oxadiazole methylsulfides (7a-7h) and the corresponding dimethylpiperazinium iodides (8a-8h), respectively. Structures were characterized by elemental analysis and spectra data, and their anticancer activities in vitro against CHO, HL60 and L1210 cancer cells were also evaluated by MTT assay. The preliminary results show that piperazinium compounds (8) possess more potent activity than that of corresponding free bases (7).
authors.affiliation: Institute of Chemistry & Biology, Henan University, Kaifeng 475001, China. hgqxy@sina.com.cn
authors.forename: Guo-qiang
authors.initials: GQ
authors.lastname: Hu
authors.forename: Li-li
authors.initials: LL
authors.lastname: Hou
authors.forename: Guo-qiang
authors.initials: GQ
authors.lastname: Wang
authors.forename: Nan-nan
authors.initials: NN
authors.lastname: Duan
authors.forename: Xiao-yi
authors.initials: XY
authors.lastname: Wen
authors.forename: Tie-yao
authors.initials: TY
authors.lastname: Cao
authors.forename: Jun
authors.initials: J
authors.lastname: Yin
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Song-qiang
authors.initials: SQ
authors.lastname: Xie
authors.forename: Wen-long
authors.initials: WL
authors.lastname: Huang
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D016466:CHO Cells; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002939:Ciprofloxacin / Q000737:chemistry*; D006224:Cricetinae; D003412:Cricetulus; D015195:Drug Design; D018922:HL-60 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D007939:Leukemia L1210; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000077489:Piperazine; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D010069:Oxadiazoles; D010879:Piperazines; D000077489:Piperazine; D002939:Ciprofloxacin