Synthesis of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic acid derivatives: New leads as selective beta-galactosidase inhibitors

The preparation of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives in a stereoselective route starting from D-glucose and ethyl acetoacetate is presented. Ethyl ester (6), N,N-diethylamide (7) and N-isopropylamide (8) have been tested towards 25 glycosidases. Ester (6) is a selective inhibitor of beta-galactosidases. The new compounds represent a new type of imino-C-nucleoside analogues. (C) 2002 Published by Elsevier Science Ltd.


Published in:
Bioorganic & Medicinal Chemistry Letters, 12, 17, 2335-2339
Year:
2002
ISSN:
0960-894X
Keywords:
Note:
Univ Sevilla, Dept Quim Organ, Fac Quim, E-41071 Seville, Spain. Ecole Polytech Fed Lausanne, Inst Chim Mol & Biol, BCH, CH-1015 Lausanne, Switzerland.
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Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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