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A Direct Synthesis of 2‐(ω‐Carboxyalkyl)isoflavones from ortho ‐Hydroxylated Deoxybenzoins
Author(s) -
Mrug Galyna P.,
Demydchuk Bohdan A.,
Bondarenko Svitlana P.,
Sviripa Vitaliy M.,
Wyrebek Przemyslaw,
Mohler James L.,
Fiandalo Michael V.,
Liu Chunming,
Frasinyuk Mykhaylo S.,
Watt David S.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801171
Subject(s) - chemistry , isoflavones , triethylamine , stereochemistry , derivative (finance) , alkyl , combinatorial chemistry , organic chemistry , biochemistry , financial economics , economics
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.