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- Title
A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues.
- Authors
Wibowo, Agustono; Shaameri, Zurina; Mohammat, Mohd Fazli; Hamzah, Ahmad Sazali
- Abstract
Some novel five-membered iminosugar analogues were efficiently synthesized via the MCRs of three components; amines, aldehydes and oxaloacetate to give 4-hydroxymethylpyrrolidines. Reduction of 3-hydroxy-4- carbomethoxy-3-pyrroliden-2-ones with Pd/C-catalyzed hydrogenation gave the corresponding cis-hydrogenated products at C3/C4 stereoselectively. Then following reductions of ester and amide functionalities with LiAlH4 afforded 4-(hydroxymethyl)pyrrolidin-3-ols. Among the synthesized compounds 4-hydrazineyl-3-hydroxymethyl-2- (4-methoxyphenyl)-N-methylpyrrolidine and 3-hydrazineyl-4-hydroxymethyl-1-methylpyrrolidine were found to be the most promising a-glucosidase inhibitor with IC50 values of 1.12 and 1.17 mM, respectively.
- Subjects
HYDROGENATION; ALDEHYDES; AMINES; ESTERS; PYRROLIDINE
- Publication
Organic Communications, 2020, Vol 13, Issue 3, p79
- ISSN
1307-6175
- Publication type
Article
- DOI
10.25135/acg.oc.85.20.08.1765