title: Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs.
abstract: A new, practical and efficient method for the synthesis of anhydrovinblastine AVBL (1f) by oxidative coupling of vindoline and catharanthine in the presence of ceric ammonium nitrate (CAN) was developed. Under the optimized reaction conditions, we synthesized a new series of amide anhydrovinblastine analogs substituted at the vindoline moiety of C-23 site and, evaluated for their proliferation inhibition against HeLa cell. The aryl-substituted derivatives showed loss of potency, while alkyl-substituted derivatives retained some of its cytotoxic potency. The iso-butylamide compound 10b and 2-furancorboxamide compound 18b displayed a similar cytotoxic potency compared to the positive control AVBL.
authors: School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, PR China.
authors: Weibin
authors: W
authors: Song
authors: Min
authors: M
authors: Lei
authors: Kun
authors: K
authors: Zhao
authors: Lingjun
authors: L
authors: Hu
authors: Yuhui
authors: Y
authors: Meng
authors: Dean
authors: D
authors: Guo
authors: Xuan
authors: X
authors: Liu
authors: Lihong
authors: L
authors: Hu
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001665:Binding Sites; D049109:Cell Proliferation; D002563:Cerium / Q000737:chemistry / Q000494:pharmacology*; D002626:Chemistry, Pharmaceutical / Q000379:methods; D002942:Circular Dichroism; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D006863:Hydrogen-Ion Concentration; D020128:Inhibitory Concentration 50; D008956:Models, Chemical; D009369:Neoplasms / Q000188:drug therapy*; D010100:Oxygen / Q000737:chemistry*; D013997:Time Factors; D014747:Vinblastine / Q000031:analogs & derivatives*; D014748:Vinca Alkaloids / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D014748:Vinca Alkaloids; D002563:Cerium; D014747:Vinblastine; D010100:Oxygen; C004653:ceric ammonium nitrate