A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues
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-...
| Published in: | Organic Communications |
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| Main Author: | |
| Format: | Article |
| Language: | English |
| Published: |
ACG Publications
2020
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| Online Access: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85096141483&doi=10.25135%2facg.oc.85.20.08.1765&partnerID=40&md5=3ad6a674c5cbaf262f5eeee75557f164 |
| Summary: | 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 LiAIH4 afforded 4-(hydroxymethyl)pyrrolidin-3-ols. Among the synthesized compounds 4-hydrazineyl-3-hydroxymethyl-2-(4-methoxyphenyl)-N-methylpyrrolidine and 3-hydrazineyl-4-hydroxymethyl-l-methylpyrrolidine were found to be the most promising a-glucosidase inhibitor with IC50 values of 1.12 and 1.17 mM, respectively. © 2020 ACG Publications. All right reserved |
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| ISSN: | 13076175 |
| DOI: | 10.25135/acg.oc.85.20.08.1765 |