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 |
|---|---|
| Main Author: | |
| Format: | Article |
| Language: | English |
| Published: |
ACG Publications
2020
|
| 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 |
| id |
2-s2.0-85096141483 |
|---|---|
| spelling |
2-s2.0-85096141483 Wibowo A.; Shaameri Z.; Mohammat M.F.; Hamzah A.S. A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues 2020 Organic Communications 13 3 10.25135/acg.oc.85.20.08.1765 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 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 ACG Publications 13076175 English Article All Open Access; Gold Open Access |
| author |
Wibowo A.; Shaameri Z.; Mohammat M.F.; Hamzah A.S. |
| spellingShingle |
Wibowo A.; Shaameri Z.; Mohammat M.F.; Hamzah A.S. A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues |
| author_facet |
Wibowo A.; Shaameri Z.; Mohammat M.F.; Hamzah A.S. |
| author_sort |
Wibowo A.; Shaameri Z.; Mohammat M.F.; Hamzah A.S. |
| title |
A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues |
| title_short |
A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues |
| title_full |
A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues |
| title_fullStr |
A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues |
| title_full_unstemmed |
A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues |
| title_sort |
A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues |
| publishDate |
2020 |
| container_title |
Organic Communications |
| container_volume |
13 |
| container_issue |
3 |
| doi_str_mv |
10.25135/acg.oc.85.20.08.1765 |
| url |
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 |
| description |
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 |
| publisher |
ACG Publications |
| issn |
13076175 |
| language |
English |
| format |
Article |
| accesstype |
All Open Access; Gold Open Access |
| record_format |
scopus |
| collection |
Scopus |
| _version_ |
1809677899066769408 |