A Direct Synthesis of 2‐(ω‐Carboxyalkyl)isoflavones from ortho‐Hydroxylated Deoxybenzoins
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.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Oct 11, 2018
- Source ID
- 10.1002/ejoc.201801171
Entities
People
- Bohdan A. Demydchuk
- Chunming Liu
- David S Watt
- Galyna P. Mrug
- James L Mohler
- Michael V Fiandalo
- Mykhaylo S Frasinyuk
- Przemyslaw Wyrebek
- Svitlana P. Bondarenko
- Vitaliy M Sviripa
Organizations
- Institute of Bioorganic Chemistry and Petrochemistry
- National Institutes of Health
- National University of Food Technologies
- Roswell Park Comprehensive Cancer Center
- United States Department of Defense
- University of Kentucky