Synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-N-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico study
The aim of the present research work was to investigate the enzyme inhibitory potential of some new sulfonamides having benzodioxane and acetamide moieties. The synthesis was started by the reaction of N-2,3-dihydrobenzo[1,4]-dioxin-6-amine (1) with 4-methylbenzenesulfonyl chloride (2) in the presence of 10% aqueous Na2CO3 to yield N-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-4-methylbenzenesulfonamide (3), which was then reacted with 2-bromo-N-(un/substituted-phenyl)acetamides (6a-l) in DMF and lithium hydride as a base to afford various 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl)sulfonyl]amino}-N-(un/substituted-phenyl)acetamides (7a-l). All the synthesized compounds were characterized by their IR and 1H-NMR spectral data along with CHN analysis data. The enzyme inhibitory activities of these compounds were tested against a-glucosidase and acetylcholinesterase (AChE). Most of the compounds exhibited substantial inhibitory activity against yeast a-glucosidase and weak against AChE. The in silico molecular docking results were also consistent with in vitro enzyme inhibition data.
Main Authors: | , , , , , , , |
---|---|
Format: | Digital revista |
Language: | English |
Published: |
Universidade de São Paulo, Faculdade de Ciências Farmacêuticas
2019
|
Online Access: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1984-82502019000100518 |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
id |
oai:scielo:S1984-82502019000100518 |
---|---|
record_format |
ojs |
spelling |
oai:scielo:S1984-825020190001005182019-08-12Synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-N-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico studyAbbasi,Muhammad AtharRiaz,SajidRehman,Aziz-ur-Siddiqui,Sabahat ZahraShah,Syed Adnan AliAshraf,MuhammadLodhi,Muhammad ArifKhan,Farman Ali Benzodioxane Acetamide Spectral analysis a-Glucosidase Acetylcholinesterase Molecular docking The aim of the present research work was to investigate the enzyme inhibitory potential of some new sulfonamides having benzodioxane and acetamide moieties. The synthesis was started by the reaction of N-2,3-dihydrobenzo[1,4]-dioxin-6-amine (1) with 4-methylbenzenesulfonyl chloride (2) in the presence of 10% aqueous Na2CO3 to yield N-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-4-methylbenzenesulfonamide (3), which was then reacted with 2-bromo-N-(un/substituted-phenyl)acetamides (6a-l) in DMF and lithium hydride as a base to afford various 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl)sulfonyl]amino}-N-(un/substituted-phenyl)acetamides (7a-l). All the synthesized compounds were characterized by their IR and 1H-NMR spectral data along with CHN analysis data. The enzyme inhibitory activities of these compounds were tested against a-glucosidase and acetylcholinesterase (AChE). Most of the compounds exhibited substantial inhibitory activity against yeast a-glucosidase and weak against AChE. The in silico molecular docking results were also consistent with in vitro enzyme inhibition data.info:eu-repo/semantics/openAccessUniversidade de São Paulo, Faculdade de Ciências FarmacêuticasBrazilian Journal of Pharmaceutical Sciences v.55 20192019-01-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S1984-82502019000100518en10.1590/s2175-97902019000117032 |
institution |
SCIELO |
collection |
OJS |
country |
Brasil |
countrycode |
BR |
component |
Revista |
access |
En linea |
databasecode |
rev-scielo-br |
tag |
revista |
region |
America del Sur |
libraryname |
SciELO |
language |
English |
format |
Digital |
author |
Abbasi,Muhammad Athar Riaz,Sajid Rehman,Aziz-ur- Siddiqui,Sabahat Zahra Shah,Syed Adnan Ali Ashraf,Muhammad Lodhi,Muhammad Arif Khan,Farman Ali |
spellingShingle |
Abbasi,Muhammad Athar Riaz,Sajid Rehman,Aziz-ur- Siddiqui,Sabahat Zahra Shah,Syed Adnan Ali Ashraf,Muhammad Lodhi,Muhammad Arif Khan,Farman Ali Synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-N-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico study |
author_facet |
Abbasi,Muhammad Athar Riaz,Sajid Rehman,Aziz-ur- Siddiqui,Sabahat Zahra Shah,Syed Adnan Ali Ashraf,Muhammad Lodhi,Muhammad Arif Khan,Farman Ali |
author_sort |
Abbasi,Muhammad Athar |
title |
Synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-N-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico study |
title_short |
Synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-N-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico study |
title_full |
Synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-N-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico study |
title_fullStr |
Synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-N-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico study |
title_full_unstemmed |
Synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-N-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico study |
title_sort |
synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-n-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico study |
description |
The aim of the present research work was to investigate the enzyme inhibitory potential of some new sulfonamides having benzodioxane and acetamide moieties. The synthesis was started by the reaction of N-2,3-dihydrobenzo[1,4]-dioxin-6-amine (1) with 4-methylbenzenesulfonyl chloride (2) in the presence of 10% aqueous Na2CO3 to yield N-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-4-methylbenzenesulfonamide (3), which was then reacted with 2-bromo-N-(un/substituted-phenyl)acetamides (6a-l) in DMF and lithium hydride as a base to afford various 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl)sulfonyl]amino}-N-(un/substituted-phenyl)acetamides (7a-l). All the synthesized compounds were characterized by their IR and 1H-NMR spectral data along with CHN analysis data. The enzyme inhibitory activities of these compounds were tested against a-glucosidase and acetylcholinesterase (AChE). Most of the compounds exhibited substantial inhibitory activity against yeast a-glucosidase and weak against AChE. The in silico molecular docking results were also consistent with in vitro enzyme inhibition data. |
publisher |
Universidade de São Paulo, Faculdade de Ciências Farmacêuticas |
publishDate |
2019 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1984-82502019000100518 |
work_keys_str_mv |
AT abbasimuhammadathar synthesisofnew223dihydro14benzodioxin6yl4methylphenylsulfonylaminonunsubstitutedphenylacetamidesasaglucosidaseandacetylcholinesteraseinhibitorsandtheirinsilicostudy AT riazsajid synthesisofnew223dihydro14benzodioxin6yl4methylphenylsulfonylaminonunsubstitutedphenylacetamidesasaglucosidaseandacetylcholinesteraseinhibitorsandtheirinsilicostudy AT rehmanazizur synthesisofnew223dihydro14benzodioxin6yl4methylphenylsulfonylaminonunsubstitutedphenylacetamidesasaglucosidaseandacetylcholinesteraseinhibitorsandtheirinsilicostudy AT siddiquisabahatzahra synthesisofnew223dihydro14benzodioxin6yl4methylphenylsulfonylaminonunsubstitutedphenylacetamidesasaglucosidaseandacetylcholinesteraseinhibitorsandtheirinsilicostudy AT shahsyedadnanali synthesisofnew223dihydro14benzodioxin6yl4methylphenylsulfonylaminonunsubstitutedphenylacetamidesasaglucosidaseandacetylcholinesteraseinhibitorsandtheirinsilicostudy AT ashrafmuhammad synthesisofnew223dihydro14benzodioxin6yl4methylphenylsulfonylaminonunsubstitutedphenylacetamidesasaglucosidaseandacetylcholinesteraseinhibitorsandtheirinsilicostudy AT lodhimuhammadarif synthesisofnew223dihydro14benzodioxin6yl4methylphenylsulfonylaminonunsubstitutedphenylacetamidesasaglucosidaseandacetylcholinesteraseinhibitorsandtheirinsilicostudy AT khanfarmanali synthesisofnew223dihydro14benzodioxin6yl4methylphenylsulfonylaminonunsubstitutedphenylacetamidesasaglucosidaseandacetylcholinesteraseinhibitorsandtheirinsilicostudy |
_version_ |
1756437847884169216 |