Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors

Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors

In search of better α-glucosidase inhibitors, a series of bis-indolylmethane sulfonohydrazides derivatives (1-14) were synthesized and evaluated for their α-glucosidase inhibitory potential. All derivatives exhibited outstanding α-glucosidase inhibition with IC...

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Published in:Bioorganic Chemistry
Main Author: Gollapalli M.; Taha M.; Ullah H.; Nawaz M.; AlMuqarrabun L.M.R.; Rahim F.; Qureshi F.; Mosaddik A.; Ahmat N.; Khan K.M.
Format: Article
Language:English
Published: Academic Press Inc. 2018
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85048198591&doi=10.1016%2fj.bioorg.2018.06.001&partnerID=40&md5=c8d5a64c98a4ca54fd171e31db6fbd90
id 2-s2.0-85048198591
spelling 2-s2.0-85048198591
Gollapalli M.; Taha M.; Ullah H.; Nawaz M.; AlMuqarrabun L.M.R.; Rahim F.; Qureshi F.; Mosaddik A.; Ahmat N.; Khan K.M.
Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors
2018
Bioorganic Chemistry
80

10.1016/j.bioorg.2018.06.001
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85048198591&doi=10.1016%2fj.bioorg.2018.06.001&partnerID=40&md5=c8d5a64c98a4ca54fd171e31db6fbd90
In search of better α-glucosidase inhibitors, a series of bis-indolylmethane sulfonohydrazides derivatives (1-14) were synthesized and evaluated for their α-glucosidase inhibitory potential. All derivatives exhibited outstanding α-glucosidase inhibition with IC 50 values ranging between 0.10 ± 0.05 to 5.1 ± 0.05 μM when compared with standard drug acarbose having IC 50 value 856.28 ± 3.15 μM. Among the series, analog 7 (0.10 ± 0.05 μM) with tri-chloro substitution on phenyl ring was identified as the most potent inhibitor of α-glucosidase (∼ 8500 times). The structure activity relationship has been also established. Molecular docking studies were also performed to help understand the binding interaction of the most active analogs with receptors. From the docking studies, it was observed that all the active bis-indolylmethane sulfonohydrazides derivatives showed considerable binding interactions within the active site (acarbose inhibition site) of α-glucosidase. We also evaluated toxicity of all derivatives and found none of them are toxic. © 2018 Elsevier Inc.
Academic Press Inc.
00452068
English
Article
author Gollapalli M.; Taha M.; Ullah H.; Nawaz M.; AlMuqarrabun L.M.R.; Rahim F.; Qureshi F.; Mosaddik A.; Ahmat N.; Khan K.M.
spellingShingle Gollapalli M.; Taha M.; Ullah H.; Nawaz M.; AlMuqarrabun L.M.R.; Rahim F.; Qureshi F.; Mosaddik A.; Ahmat N.; Khan K.M.
Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors
author_facet Gollapalli M.; Taha M.; Ullah H.; Nawaz M.; AlMuqarrabun L.M.R.; Rahim F.; Qureshi F.; Mosaddik A.; Ahmat N.; Khan K.M.
author_sort Gollapalli M.; Taha M.; Ullah H.; Nawaz M.; AlMuqarrabun L.M.R.; Rahim F.; Qureshi F.; Mosaddik A.; Ahmat N.; Khan K.M.
title Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors
title_short Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors
title_full Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors
title_fullStr Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors
title_full_unstemmed Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors
title_sort Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors
publishDate 2018
container_title Bioorganic Chemistry
container_volume 80
container_issue
doi_str_mv 10.1016/j.bioorg.2018.06.001
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85048198591&doi=10.1016%2fj.bioorg.2018.06.001&partnerID=40&md5=c8d5a64c98a4ca54fd171e31db6fbd90
description In search of better α-glucosidase inhibitors, a series of bis-indolylmethane sulfonohydrazides derivatives (1-14) were synthesized and evaluated for their α-glucosidase inhibitory potential. All derivatives exhibited outstanding α-glucosidase inhibition with IC 50 values ranging between 0.10 ± 0.05 to 5.1 ± 0.05 μM when compared with standard drug acarbose having IC 50 value 856.28 ± 3.15 μM. Among the series, analog 7 (0.10 ± 0.05 μM) with tri-chloro substitution on phenyl ring was identified as the most potent inhibitor of α-glucosidase (∼ 8500 times). The structure activity relationship has been also established. Molecular docking studies were also performed to help understand the binding interaction of the most active analogs with receptors. From the docking studies, it was observed that all the active bis-indolylmethane sulfonohydrazides derivatives showed considerable binding interactions within the active site (acarbose inhibition site) of α-glucosidase. We also evaluated toxicity of all derivatives and found none of them are toxic. © 2018 Elsevier Inc.
publisher Academic Press Inc.
issn 00452068
language English
format Article
accesstype
record_format scopus
collection Scopus
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