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Monocyclic, Substituted Imidazoles as Glycosidase Inhibitors
Author(s) -
Magdolen Peter,
Vasella Andrea
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200590182
Subject(s) - chemistry , imidazole , stereochemistry , glycoside hydrolase , yeast , enzyme , medicinal chemistry , organic chemistry , biochemistry
A range of 4‐monosubstituted and 2,4‐disubstituted 1 H ‐imidazoles and 1 H ‐imidazole‐1‐ethanols (RC(4): CH 2 CH 2 Ph, CHOHCH 2 Ph, Ph, or Me; RC(2): CH 2 OH, CHOHCH 2 OH, CN, or CH 2 NHAc) were prepared and tested as inhibitors of α ‐ and β ‐glucosidases and of a β ‐galactosidase. A new access to 4‐(2‐phenylethyl)‐1 H ‐imidazoles starting from 4‐phenylbutan‐1‐ol was elaborated. The strongest inhibitors are the 2‐substituted 4‐(2‐phenylethyl)‐1 H ‐imidazoles 24a and 26a (RC(2): CH 2 OH and CHOHCH 2 OH) and the 2‐phenylethanol 34 . They inhibit the β ‐galactosidase from bovine liver and the β ‐glucosidase from Caldocellum saccharolyticum with inhibition constants in the micromolar range, but do not inhibit the α ‐glucosidase from brewer's yeast.