1591782-93-2Relevant academic research and scientific papers
Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors
Ayers, Benjamin J.,Glawar, Andreas F. G.,Martínez, R. Fernando,Ngo, Nigel,Liu, Zilei,Fleet, George W. J.,Butters, Terry D.,Nash, Robert J.,Yu, Chu-Yi,Wormald, Mark R.,Nakagawa, Shinpei,Adachi, Isao,Kato, Atsushi,Jenkinson, Sarah F.
, p. 3398 - 3409 (2014/05/06)
All 16 stereoisomeric N-methyl 5-(hydroxymethyl)-3,4-dihydroxyproline amides have been synthesized from lactones accessible from the enantiomers of glucuronolactone. Nine stereoisomers, including all eight with a (3R)-hydroxyl configuration, are low to submicromolar inhibitors of β-N- acetylhexosaminidases. A structural correlation between the proline amides is found with the ADMDP-acetamide analogues bearing an acetamidomethylpyrrolidine motif. The proline amides are generally more potent than their ADMDP-acetamide equivalents. β-N-Acetylhexosaminidase inhibition by an azetidine ADMDP-acetamide analogue is compared to an azetidine carboxylic acid amide. None of the amides are good α-N-acetylgalactosaminidase inhibitors.
