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Synthetic Routes to Three Novel Scaffolds for Potential Glycosidase Inhibitors
Author(s) -
Rommel Michael,
Ernst Alexander,
Koert Ulrich
Publication year - 2007
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.200700333
Subject(s) - chemistry , scaffold , substituent , intramolecular force , glycoside hydrolase , stereochemistry , olefin fiber , combinatorial chemistry , enzyme , organic chemistry , catalysis , medicine , biomedical engineering
Efficient syntheses of three novel scaffolds for potential β‐glycosidase inhibitors were developed: The first consists of a 2,7‐dioxabicyclo[2.2.1]heptane derivative, which was prepared by an intramolecular ketalisation. The second scaffold consists of a hydroxylated cyclopentylamine, which could be synthesised stereoselectively from 2‐azabicyclo[2.2.1]hept‐5‐en‐3‐one. The third scaffold, a 4,5‐dihydroxynicotinic acid, was accessible through a sequence of substituent directed ortho ‐lithiations. Selected compounds were tested as inhibitors for a number of glycosidases. Three nicotinic acid derivatives were found to be selective β‐glucosidase inhibitors.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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