Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions

Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions

2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their α-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC50 values in the range of 2.3 ± 0.11-226.4 ± 6.8 μM was observed while comparing these outcomes with the standard acarbose (IC50 = 906.0±6.3μM). Th...

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Published in:Bioorganic Chemistry
Main Author: Taha M.; Ismail N.H.; Javaid K.; Imran S.; Anouar E.H.; Wadood A.; Atia-Tul-Wahab; Ali M.; Khan K.M.; Saad S.M.; Rahim F.; Choudhary M.I.
Format: Article
Language:English
Published: Academic Press Inc. 2015
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-84942794211&doi=10.1016%2fj.bioorg.2015.09.001&partnerID=40&md5=ab9d824d62006e2a5510d5dd701506c3
id 2-s2.0-84942794211
spelling 2-s2.0-84942794211
Taha M.; Ismail N.H.; Javaid K.; Imran S.; Anouar E.H.; Wadood A.; Atia-Tul-Wahab; Ali M.; Khan K.M.; Saad S.M.; Rahim F.; Choudhary M.I.
Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions
2015
Bioorganic Chemistry
63

10.1016/j.bioorg.2015.09.001
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84942794211&doi=10.1016%2fj.bioorg.2015.09.001&partnerID=40&md5=ab9d824d62006e2a5510d5dd701506c3
2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their α-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC50 values in the range of 2.3 ± 0.11-226.4 ± 6.8 μM was observed while comparing these outcomes with the standard acarbose (IC50 = 906.0±6.3μM). The stereochemistry of ten (10) randomly selected compounds (1, 3, 6, 8, 12, 18, 19, 23, 25 and 28) was predicted by Density Functional Theory (DFT). The stability of E isomer was deduced by comparing the calculated and experimental vibration modes of νC=O, νN=C and νCH (CH in -N=CH-R). It was observed that except compound 18, all other compounds were deduced to have E configuration while molecular modeling studies revealed the key interactions between enzyme and synthesized compounds. © 2015 Elsevier Inc. All rights reserved.
Academic Press Inc.
452068
English
Article
author Taha M.; Ismail N.H.; Javaid K.; Imran S.; Anouar E.H.; Wadood A.; Atia-Tul-Wahab; Ali M.; Khan K.M.; Saad S.M.; Rahim F.; Choudhary M.I.
spellingShingle Taha M.; Ismail N.H.; Javaid K.; Imran S.; Anouar E.H.; Wadood A.; Atia-Tul-Wahab; Ali M.; Khan K.M.; Saad S.M.; Rahim F.; Choudhary M.I.
Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions
author_facet Taha M.; Ismail N.H.; Javaid K.; Imran S.; Anouar E.H.; Wadood A.; Atia-Tul-Wahab; Ali M.; Khan K.M.; Saad S.M.; Rahim F.; Choudhary M.I.
author_sort Taha M.; Ismail N.H.; Javaid K.; Imran S.; Anouar E.H.; Wadood A.; Atia-Tul-Wahab; Ali M.; Khan K.M.; Saad S.M.; Rahim F.; Choudhary M.I.
title Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions
title_short Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions
title_full Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions
title_fullStr Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions
title_full_unstemmed Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions
title_sort Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions
publishDate 2015
container_title Bioorganic Chemistry
container_volume 63
container_issue
doi_str_mv 10.1016/j.bioorg.2015.09.001
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-84942794211&doi=10.1016%2fj.bioorg.2015.09.001&partnerID=40&md5=ab9d824d62006e2a5510d5dd701506c3
description 2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their α-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC50 values in the range of 2.3 ± 0.11-226.4 ± 6.8 μM was observed while comparing these outcomes with the standard acarbose (IC50 = 906.0±6.3μM). The stereochemistry of ten (10) randomly selected compounds (1, 3, 6, 8, 12, 18, 19, 23, 25 and 28) was predicted by Density Functional Theory (DFT). The stability of E isomer was deduced by comparing the calculated and experimental vibration modes of νC=O, νN=C and νCH (CH in -N=CH-R). It was observed that except compound 18, all other compounds were deduced to have E configuration while molecular modeling studies revealed the key interactions between enzyme and synthesized compounds. © 2015 Elsevier Inc. All rights reserved.
publisher Academic Press Inc.
issn 452068
language English
format Article
accesstype
record_format scopus
collection Scopus
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