Skip to Content
MilliporeSigma
  • Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs.

Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs.

Bioorganic & medicinal chemistry letters (2011-11-26)
Weibin Song, Min Lei, Kun Zhao, Lingjun Hu, Yuhui Meng, Dean Guo, Xuan Liu, Lihong Hu
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ammonium cerium(IV) nitrate, JIS special grade, ≥95.0%
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ≥99.99% trace metals basis
Sigma-Aldrich
Ammonium cerium(IV) nitrate, puriss. p.a., ACS reagent, ≥98.5% (RT)
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ≥98% (titration)
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ACS reagent, ≥98.5%