title: The effect of vindoline C-16 substituents on the biomimetic coupling reaction: synthesis and cytotoxicity evaluation of the corresponding vinorelbine analogues.
abstract: A new series of vinorelbine analogues are designed and synthesized to explore the vindoline C-16 substituent effects on the biomimetic coupling with catharanthine, and the structure-activity relationships of these vinorelbine analogues as cytotoxic agents are also studied. The results show that introduction of severe steric hindrance and/or electron-withdrawing group at C-16 site are not propitious to improving the yields of the coupling reaction, and the SAR information collected so far suggests that small alkyl groups substituted at C-16 of vindoline are conductive to maintaining the cytotoxicity.
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, PR China.
authors.forename: Weibin
authors.initials: W
authors.lastname: Song
authors.forename: Lingjun
authors.initials: L
authors.lastname: Hu
authors.forename: Yuhui
authors.initials: Y
authors.lastname: Meng
authors.forename: Lei
authors.initials: L
authors.lastname: Ma
authors.forename: Dean
authors.initials: D
authors.lastname: Guo
authors.forename: Xuan
authors.initials: X
authors.lastname: Liu
authors.forename: Lihong
authors.initials: L
authors.lastname: Hu
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D032701:Biomimetics; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D013329:Structure-Activity Relationship; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000972:Antineoplastic Agents, Phytogenic; C009667:vindoline; D014747:Vinblastine