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Synthesis of potent β-D-glucocerebrosidase inhibitors: N-alkyl-β-valienamines

✍ Scribed by Seiichiro Ogawa; Makoto Ashiura; Chikara Uchida; Shinsuke Watanabe; Chihiro Yamazaki; Kiwamu Yamagishi; Jin-ichi Inokuchi

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
193 KB
Volume
6
Category
Article
ISSN
0960-894X

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✦ Synopsis

Six homologous derivatives (N-butyl 3a, hexyl 3b, octyl 3e, decyl 3d, tetradecyl 3e and stearyl 3t) of [5-valienamine were synthesized. All have been shown to be potent and specific inhibitors of I~-glucocerebrosidase, and to have no potency against glucosylceramide synthase (mouse liver microsomes). Among them, the N-octyl derivative possesses the strongest activity (IC50 3 x 10 .8 M), being almost 10-fold more potent compared to the unsaturated 5a-carba-glucosylceramide 1. Compounds 3b and 3e are also moderate inhibitors of ot-glucosidase (Bakers yeast).

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