TY - JOUR
T1 - A Direct Synthesis of 2-(ω-Carboxyalkyl)isoflavones from ortho-Hydroxylated Deoxybenzoins
AU - Mrug, Galyna P.
AU - Demydchuk, Bohdan A.
AU - Bondarenko, Svitlana P.
AU - Sviripa, Vitaliy M.
AU - Wyrebek, Przemyslaw
AU - Mohler, James L.
AU - Fiandalo, Michael V.
AU - Liu, Chunming
AU - Frasinyuk, Mykhaylo S.
AU - Watt, David S.
N1 - Publisher Copyright:
© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/10/24
Y1 - 2018/10/24
N2 - 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.
AB - 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.
KW - Cyclic anhydride
KW - Isoflavone
KW - Natural products
KW - Ring-closure
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U2 - 10.1002/ejoc.201801171
DO - 10.1002/ejoc.201801171
M3 - Article
AN - SCOPUS:85054741670
SN - 1434-193X
VL - 2018
SP - 5460
EP - 5463
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 39
ER -