A Direct Synthesis of 2-(ω-Carboxyalkyl)isoflavones from ortho-Hydroxylated Deoxybenzoins

Galyna P. Mrug, Bohdan A. Demydchuk, Svitlana P. Bondarenko, Vitaliy M. Sviripa, Przemyslaw Wyrebek, James L. Mohler, Michael V. Fiandalo, Chunming Liu, Mykhaylo S. Frasinyuk, David S. Watt

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

As part of a program focused on the development of new antineoplastic agents based on scaffolds found in natural products, we explored the isoflavone family as potential enzyme inhibitors. We required biotin-modified isoflavones to identify potential biological targets, and we selected the C-2 position in isoflavones as an attachment site for an alkyl group bearing a terminal carboxylic acid to which we could attach a biotin derivative. The base-catalyzed condensation of 2,4-dihydroxy-substituted deoxybenzoins with cyclic anhydrides mediated by a combination of triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene led to an efficient synthesis of the desired 2-(ω-carboxyalkyl)isoflavones with functional groups at C-5, 6 and 7 and with various substituents in the C-3 phenyl group.

Original languageEnglish
Pages (from-to)5460-5463
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number39
DOIs
StatePublished - Oct 24 2018

Bibliographical note

Publisher Copyright:
© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Cyclic anhydride
  • Isoflavone
  • Natural products
  • Ring-closure

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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