Synthesis of epigallocatechin trimer, (epigallocatechin)(2)-epicatechin, and (epigallocatechin)(2)-catechin via a Lewis acid mediated one-pot condensation and their antitumor activities in prostate cancer cells

摘要

Syntheses of epigallocatechin trimer, (epigallocatechin)(2)-epicatechin and (epigallocatechin)(2)-catechin were achieved. The key condensation to form the proanthocyanidin trimer derivatives was accomplished in a one-pot procedure using a dimeric epigallocatechin electrophile, which was prepared in situ by self-condensation of an epigallocatechin derivative, and an epigallocatechin, epicatechin, or catechin derivative as the nucleophile in the presence of a Lewis acid. The epigallocatechin monomer to trimer compounds containing a pyrogallol group significantly suppressed cell proliferation in PC-3 prostate cancer cells. (C) 2018 Elsevier Ltd. All rights reserved.