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2′‐ O ‐Alkyl Derivatives and 5′‐Analogues of 5‐Aminoimidazole‐4‐carboxamide‐1‐β‐ D ‐ribofuranoside (AICAR) as Potential Hsp90 Inhibitors
Author(s) -
Bracci Antonio,
Colombo Giorgio,
Ronchetti Fiamma,
Compostella Federica
Publication year - 2009
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.200900797
Subject(s) - chemistry , moiety , pyrimidine , alkylation , residue (chemistry) , stereochemistry , hypoxanthine , combinatorial chemistry , carboxamide , biochemistry , enzyme , catalysis
Some selective preparations of AICAR‐related compounds modified at the 2′‐ or 5′‐position of the ribose moiety are reported herein. In particular, 5′‐azido, 5′‐amino, 5′‐ O ‐benzyl and a series of 2′‐ O ‐alkylated AICAR derivatives have been synthesized. These compounds were derived from appropriately functionalized inosines by opening the pyrimidine ring at the hypoxanthine residue. The target derivatives were designed with the purpose of studying the effect of AICAR structural modifications on its ability to inhibit Hsp90, one of the biological targets for the development of anticancer agents. Nevertheless, the development of AICAR‐like compounds is an appealing objective also because of their potential therapeutic application in the field of metabolic studies.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)