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Synthesis of Fusion-Isomeric Imidazopyridines and Their Evaluation as Inhibitors of syn- and anti-Protonating Glycosidases

✍ Scribed by Narinder Mohal; Andrea Vasella

Book ID
102259165
Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
252 KB
Volume
88
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The galacto‐ and __gluco‐__configured imidazopyridines 4 and 5 were synthesised as potential inhibitors of syn‐protonating β‐glycosidases. Methyl α‐D‐lyxopyranoside (9) was transformed into the 3,4‐anhydro‐β‐L‐riboside 16, which, upon treatment with Et~2~AlCN, gave the nitrile 17 (76–85%). Reaction of 17 with the dimethyl aluminate of aminoacetaldehyde dimethyl acetal led directly to the branched chain lyxo‐configured imidazole 27 (53%) that was hydrolysed to an equilibrating mixture of 4 and 28–30. Oxido reduction of 27 provided the arabino‐configured imidazole 42 (ca. 48% from 27). Hydrolysis of 42 led to the mixture 5/45 (63–90%). anti‐Protonating β‐galactosidases and β‐glucosidases (families 1 and 2) were only weakly inhibited by 4/28–30 and 5/45, respectively. Also the syn‐protonating cellulase (Cel7A) was weakly inhibited by the monosaccharide mimics 5/45, suggesting either that monosaccharide mimics are too small to inhibit Cel7A, or that fusion isomeric tetrahydroimidazo[1,2‐a]pyridines are not a suitable scaffold for the inhibition of syn‐protonating glycosidases.

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