Synthesis of modified 1,3,4-thiadiazole incorporating substituted thiosemicarbazide derivatives: Elucidating the in vitro and in silico studies to develop promising anti-diabetic agent

Synthesis of modified 1,3,4-thiadiazole incorporating substituted thiosemicarbazide derivatives: Elucidating the in vitro and in silico studies to develop promising anti-diabetic agent

Hybrid molecules based on the 1,3,4-thiadiazole were always the choice of different researchers due to their significant application in medicinal as well as pharmaceutical application. In the present study, twenty analogs of 1,3,4-thiadiazole-bearing thiosemicarbazide moiety (1–20) were synthesized...

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Published in:Results in Chemistry
Main Author: Abbasi S.A.; Rahim F.; Hussain R.; Khan S.; Ullah H.; Iqbal T.; Iqbal N.; Khan H.U.; Khan S.; Iqbal R.; Shah S.A.A.; Al Obaid S.; Ansari M.J.
Format: Article
Language:English
Published: Elsevier B.V. 2024
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85194360615&doi=10.1016%2fj.rechem.2024.101556&partnerID=40&md5=98bec11c32832296edf3193fc8e67c5d
id 2-s2.0-85194360615
spelling 2-s2.0-85194360615
Abbasi S.A.; Rahim F.; Hussain R.; Khan S.; Ullah H.; Iqbal T.; Iqbal N.; Khan H.U.; Khan S.; Iqbal R.; Shah S.A.A.; Al Obaid S.; Ansari M.J.
Synthesis of modified 1,3,4-thiadiazole incorporating substituted thiosemicarbazide derivatives: Elucidating the in vitro and in silico studies to develop promising anti-diabetic agent
2024
Results in Chemistry
8

10.1016/j.rechem.2024.101556
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85194360615&doi=10.1016%2fj.rechem.2024.101556&partnerID=40&md5=98bec11c32832296edf3193fc8e67c5d
Hybrid molecules based on the 1,3,4-thiadiazole were always the choice of different researchers due to their significant application in medicinal as well as pharmaceutical application. In the present study, twenty analogs of 1,3,4-thiadiazole-bearing thiosemicarbazide moiety (1–20) were synthesized and screened for their anti-diabetic profile. The synthesized compounds were spectroscopically characterized through different spectroscopic techniques such as 1HNMR, 13CNMR, and HREI-MS. Comparing the whole set of afforded compounds to the standard glimepiride drugs (16.01 ± 0.02 μM), the inhibition profiles against α-amylase ranged from 21.02 ± 0.08 to 54.08 ± 0.04 μM. Comparing synthetic analogs to normal glimepiride (IC50 = 14.06 ± 0.05 μM), the range of α-glucosidase activity was likewise variable, ranging from 18.04 ± 0.07 μM to IC50 = 51.05 ± 0.03 μM (against α-glucosidase). Compound 19 demonstrated high potency among the produced analogs since it had both ortho-nitro substitution at the aryl ring. The pattern of substitutions around the aryl ring was used for all analogs to determine the structure–activity relationship. In addition, a molecular docking study was conducted on the potent analogs to examine the interactions between the active residues of the targeted enzymes with the synthesized compound. The synthesized molecule showed different types of interactions with amino acid. The outcome demonstrates that these compounds provide several essential interactions with the active sites of enzymes, hence strengthening their enzymatic activity for the future prediction as drug competitors. © 2024 The Authors
Elsevier B.V.
22117156
English
Article
author Abbasi S.A.; Rahim F.; Hussain R.; Khan S.; Ullah H.; Iqbal T.; Iqbal N.; Khan H.U.; Khan S.; Iqbal R.; Shah S.A.A.; Al Obaid S.; Ansari M.J.
spellingShingle Abbasi S.A.; Rahim F.; Hussain R.; Khan S.; Ullah H.; Iqbal T.; Iqbal N.; Khan H.U.; Khan S.; Iqbal R.; Shah S.A.A.; Al Obaid S.; Ansari M.J.
Synthesis of modified 1,3,4-thiadiazole incorporating substituted thiosemicarbazide derivatives: Elucidating the in vitro and in silico studies to develop promising anti-diabetic agent
author_facet Abbasi S.A.; Rahim F.; Hussain R.; Khan S.; Ullah H.; Iqbal T.; Iqbal N.; Khan H.U.; Khan S.; Iqbal R.; Shah S.A.A.; Al Obaid S.; Ansari M.J.
author_sort Abbasi S.A.; Rahim F.; Hussain R.; Khan S.; Ullah H.; Iqbal T.; Iqbal N.; Khan H.U.; Khan S.; Iqbal R.; Shah S.A.A.; Al Obaid S.; Ansari M.J.
title Synthesis of modified 1,3,4-thiadiazole incorporating substituted thiosemicarbazide derivatives: Elucidating the in vitro and in silico studies to develop promising anti-diabetic agent
title_short Synthesis of modified 1,3,4-thiadiazole incorporating substituted thiosemicarbazide derivatives: Elucidating the in vitro and in silico studies to develop promising anti-diabetic agent
title_full Synthesis of modified 1,3,4-thiadiazole incorporating substituted thiosemicarbazide derivatives: Elucidating the in vitro and in silico studies to develop promising anti-diabetic agent
title_fullStr Synthesis of modified 1,3,4-thiadiazole incorporating substituted thiosemicarbazide derivatives: Elucidating the in vitro and in silico studies to develop promising anti-diabetic agent
title_full_unstemmed Synthesis of modified 1,3,4-thiadiazole incorporating substituted thiosemicarbazide derivatives: Elucidating the in vitro and in silico studies to develop promising anti-diabetic agent
title_sort Synthesis of modified 1,3,4-thiadiazole incorporating substituted thiosemicarbazide derivatives: Elucidating the in vitro and in silico studies to develop promising anti-diabetic agent
publishDate 2024
container_title Results in Chemistry
container_volume 8
container_issue
doi_str_mv 10.1016/j.rechem.2024.101556
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85194360615&doi=10.1016%2fj.rechem.2024.101556&partnerID=40&md5=98bec11c32832296edf3193fc8e67c5d
description Hybrid molecules based on the 1,3,4-thiadiazole were always the choice of different researchers due to their significant application in medicinal as well as pharmaceutical application. In the present study, twenty analogs of 1,3,4-thiadiazole-bearing thiosemicarbazide moiety (1–20) were synthesized and screened for their anti-diabetic profile. The synthesized compounds were spectroscopically characterized through different spectroscopic techniques such as 1HNMR, 13CNMR, and HREI-MS. Comparing the whole set of afforded compounds to the standard glimepiride drugs (16.01 ± 0.02 μM), the inhibition profiles against α-amylase ranged from 21.02 ± 0.08 to 54.08 ± 0.04 μM. Comparing synthetic analogs to normal glimepiride (IC50 = 14.06 ± 0.05 μM), the range of α-glucosidase activity was likewise variable, ranging from 18.04 ± 0.07 μM to IC50 = 51.05 ± 0.03 μM (against α-glucosidase). Compound 19 demonstrated high potency among the produced analogs since it had both ortho-nitro substitution at the aryl ring. The pattern of substitutions around the aryl ring was used for all analogs to determine the structure–activity relationship. In addition, a molecular docking study was conducted on the potent analogs to examine the interactions between the active residues of the targeted enzymes with the synthesized compound. The synthesized molecule showed different types of interactions with amino acid. The outcome demonstrates that these compounds provide several essential interactions with the active sites of enzymes, hence strengthening their enzymatic activity for the future prediction as drug competitors. © 2024 The Authors
publisher Elsevier B.V.
issn 22117156
language English
format Article
accesstype
record_format scopus
collection Scopus
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