Application of Mannich bases to the synthesis of hydroxymethylated isoflavonoids as potential antineoplastic agents

Mykhaylo S. Frasinyuk, Galyna P. Mrug, Svitlana P. Bondarenko, Vitaliy M. Sviripa, Wen Zhang, Xianfeng Cai, Michael V. Fiandalo, James L. Mohler, Chunming Liu, David S. Watt

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

The regiospecific Mannich aminomethylation of 7-hydroxyisoflavonoids using bis(N,N-dimethylamino)methane afforded C-8 substituted N,N-dimethylaminomethyl adducts, and the regioselective aminomethylation of 5-hydroxy-7-methoxyisoflavonoids afforded predominantly the C-6 substituted N,N-dimethylaminomethyl adducts. Acetylation of these C-6 or C-8 Mannich bases with potassium acetate in acetic anhydride provided access to the corresponding acetoxymethyl derivatives that were subsequently converted to hydroxymethyl- and methoxymethyl-substituted 5-hydroxy- or 7-hydroxyisoflavonoids related to naturally occurring flavonoids. The C-8 acetoxymethyl, hydroxymethyl or methoxymethyl-substituted isoflavonoids possessed promising inhibitory potency in the low micromolar range in a prostate cancer PC-3 cell proliferation assay.

Original languageEnglish
Pages (from-to)11292-11301
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number46
DOIs
StatePublished - Sep 23 2015

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Application of Mannich bases to the synthesis of hydroxymethylated isoflavonoids as potential antineoplastic agents'. Together they form a unique fingerprint.

Cite this