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Synthesis of Fusion-Isomeric Imidazopyridines and Their Evaluation as Inhibitors of syn- and anti-Protonating Glycosidases by Narinder Mohal; Andrea Vasella is a Chemistry article available to read on EtoBox.

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## 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 th

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Author

Narinder Mohal; Andrea Vasella

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

2005

Language

EN

Field

Chemistry (Physical Sciences)