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A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues.
- Source :
-
Organic Communications . Jul-Sep2020, Vol. 13 Issue 3, p79-88. 10p. - Publication Year :
- 2020
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *HYDROGENATION
*ALDEHYDES
*AMINES
*ESTERS
*PYRROLIDINE
Subjects
Details
- Language :
- English
- ISSN :
- 13076175
- Volume :
- 13
- Issue :
- 3
- Database :
- Academic Search Index
- Journal :
- Organic Communications
- Publication Type :
- Academic Journal
- Accession number :
- 146698526
- Full Text :
- https://doi.org/10.25135/acg.oc.85.20.08.1765