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The synthesis and biological evaluation of 1-C-alkyl-L-arabinoiminofuranoses, a novel class of α-glucosidase inhibitors.
- Source :
-
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2011 Jan 15; Vol. 21 (2), pp. 738-41. Date of Electronic Publication: 2010 Nov 30. - Publication Year :
- 2011
-
Abstract
- The asymmetric synthesis of 1-C-alkyl-l-arabinoiminofuranoses 1 was achieved by asymmetric allylic alkylation (AAA), ring closing metathesis (RCM), and Negishi cross coupling as key reactions. Some of the prepared compounds showed potent inhibitory activities towards intestinal maltase, with IC(50) values comparable to those of commercial drugs such as acarbose, voglibose, and miglitol, which are used in the treatment of type 2 diabetes. Among them, the inhibitory activity (IC(50)=0.032μM) towards intestinal sucrase of 1c was quite strong compared to the above commercial drugs.<br /> (Copyright © 2010 Elsevier Ltd. All rights reserved.)
- Subjects :
- Animals
Diabetes Mellitus, Type 2 drug therapy
Diabetes Mellitus, Type 2 enzymology
Enzyme Inhibitors chemical synthesis
Humans
Hypoglycemic Agents chemical synthesis
Hypoglycemic Agents chemistry
Hypoglycemic Agents pharmacology
Imino Furanoses chemical synthesis
Rats
Enzyme Inhibitors chemistry
Enzyme Inhibitors pharmacology
Glycoside Hydrolase Inhibitors
Imino Furanoses chemistry
Imino Furanoses pharmacology
alpha-Glucosidases metabolism
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3405
- Volume :
- 21
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry letters
- Publication Type :
- Academic Journal
- Accession number :
- 21185187
- Full Text :
- https://doi.org/10.1016/j.bmcl.2010.11.112