title: [Synthesis and anti-proliferative activity of fluoroquinolone (rhodanine unsaturated ketone) amide derivatives].
abstract: To discover novel antitumor rhodanine unsaturated ketones, a series of fluoroquinolone (rhodanine α, β-unsaturated ketone) amine derivatives (5a-5r) were designed and synthesized with fluoroquinolone amide scaffold as a carrier. The structures of eighteen title compounds were characterized by elemental analysis, 1H NMR and MS. The in vitro anti-proliferative activity against Hep-3B, Capan-1 and HL60 cells was evaluated by MTT assay. The results showed that the title compounds not only had more significant anti-proliferative activity against three tested cancer cell lines than that of the parent ciprofloxacin 1, but also exhibited the highest activity against Capan-1 cells. The SAR revealed that some compounds carrying aromatic heterocyclic rings or phenyl attached to an electron-withdrawing carboxyl or sulfonamide substituent were comparable to or better than comparison doxorubicin against Capan-1 cells. As such, it suggests that fluoroquinolone (rhodanine α, β-unsaturated ketone) amines are promising leads for the development of novel antitumor fluoroquinolones or rhodanine analogues.
authors.forename: Liu-zhou
authors.initials: LZ
authors.lastname: Gao
authors.forename: Yu-suo
authors.initials: YS
authors.lastname: Xie
authors.forename: Qiang
authors.initials: Q
authors.lastname: Yan
authors.forename: Shu-min
authors.initials: SM
authors.lastname: Wu
authors.forename: Li-li
authors.initials: LL
authors.lastname: Ni
authors.forename: Hui
authors.initials: H
authors.lastname: Zhao
authors.forename: Wen-long
authors.initials: WL
authors.lastname: Huang
authors.forename: Guo-qiang
authors.initials: GQ
authors.lastname: Hu
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D024841:Fluoroquinolones / Q000138:chemical synthesis* / Q000494:pharmacology*; D018922:HL-60 Cells; D006801:Humans; D007659:Ketones / Q000138:chemical synthesis / Q000494:pharmacology; D012236:Rhodanine / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000577:Amides; D000970:Antineoplastic Agents; D024841:Fluoroquinolones; D007659:Ketones; D012236:Rhodanine