Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities

Bioorg Med Chem Lett. 2013 Sep 1;23(17):4935-9. doi: 10.1016/j.bmcl.2013.06.061. Epub 2013 Jun 29.

Abstract

Synthesis of procyanidin B2 and B3 gallate derivatives, 3-O-gallate, 3"-O-gallate, and 3,3"-di-O-gallate, were synthesized using equimolar condensation mediated by Yb(OTf)3. Synthesized compounds showed significant antitumor effects against human prostate PC-3 cell lines. Their activities were weaker than well-known EGCG and prodelphinidin B3.

Keywords: Antitumor; Condensation; Lewis acid; Polyphenol; Procyanidin gallate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Biflavonoids / chemical synthesis
  • Biflavonoids / chemistry*
  • Biflavonoids / pharmacology*
  • Catechin / chemical synthesis
  • Catechin / chemistry*
  • Catechin / pharmacology*
  • Cell Line, Tumor
  • Gallic Acid / chemical synthesis
  • Gallic Acid / chemistry
  • Gallic Acid / pharmacology
  • Humans
  • Male
  • Mesylates / chemistry*
  • Organometallic Compounds / chemistry*
  • Proanthocyanidins / chemical synthesis
  • Proanthocyanidins / chemistry*
  • Proanthocyanidins / pharmacology*
  • Prostatic Neoplasms / drug therapy

Substances

  • Antineoplastic Agents
  • Biflavonoids
  • Mesylates
  • Organometallic Compounds
  • Proanthocyanidins
  • procyanidin B2
  • procyanidin B3
  • ytterbium(III) triflate
  • Gallic Acid
  • Catechin