Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies

Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies

In searchof the potenttherapeutic agent as an α-glucosidase inhibitor, we have synthesized twenty-five analogs (1–25) of quinoline-based Schiff bases as an inhibitoragainst α-glucosidase enzyme under positive control acarbose (IC50 = 38.45 ± 0.80 µM). From the activity profile it was foundthat analo...

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Published in:Bioorganic and Medicinal Chemistry
Main Author: Taha M.; Sultan S.; Imran S.; Rahim F.; Zaman K.; Wadood A.; Ur Rehman A.; Uddin N.; Mohammed Khan K.
Format: Article
Language:English
Published: Elsevier Ltd 2019
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85069971619&doi=10.1016%2fj.bmc.2019.07.035&partnerID=40&md5=6c1dae4e50ca9d71d8e319c5e61a39dc
id 2-s2.0-85069971619
spelling 2-s2.0-85069971619
Taha M.; Sultan S.; Imran S.; Rahim F.; Zaman K.; Wadood A.; Ur Rehman A.; Uddin N.; Mohammed Khan K.
Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies
2019
Bioorganic and Medicinal Chemistry
27
18
10.1016/j.bmc.2019.07.035
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85069971619&doi=10.1016%2fj.bmc.2019.07.035&partnerID=40&md5=6c1dae4e50ca9d71d8e319c5e61a39dc
In searchof the potenttherapeutic agent as an α-glucosidase inhibitor, we have synthesized twenty-five analogs (1–25) of quinoline-based Schiff bases as an inhibitoragainst α-glucosidase enzyme under positive control acarbose (IC50 = 38.45 ± 0.80 µM). From the activity profile it was foundthat analogs 1, 2, 3, 4, 11, 12 and 20with IC50values 12.40 ± 0.40, 9.40 ± 0.30, 14.10 ± 0.40, 6.20 ± 0.30, 14.40 ± 0.40, 7.40 ± 0.20 and 13.20 ± 0.40 µMrespectively showed most potent inhibition among the series even than standard drug acarbose (IC50 = 38.45 ± 0.80 µM). Here in the present study analog 4 (IC50 = 6.20 ± 0.30 µM) was found with many folds better α-glucosidase inhibitory activity than the reference drug. Eight analogs like 5, 7, 8, 16, 17, 22, 24 and 25 among the whole series displayed less than 50% inhibition. The substituents effects on phenyl ring thereby superficially established through SAR study. Binding interactions of analogs and the active site of ligands proteins were confirmed through molecular docking study. Spectroscopic techniques like 1H NMR, 13C NMR and ESIMS were used for characterization. © 2019 Elsevier Ltd
Elsevier Ltd
9680896
English
Article
author Taha M.; Sultan S.; Imran S.; Rahim F.; Zaman K.; Wadood A.; Ur Rehman A.; Uddin N.; Mohammed Khan K.
spellingShingle Taha M.; Sultan S.; Imran S.; Rahim F.; Zaman K.; Wadood A.; Ur Rehman A.; Uddin N.; Mohammed Khan K.
Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies
author_facet Taha M.; Sultan S.; Imran S.; Rahim F.; Zaman K.; Wadood A.; Ur Rehman A.; Uddin N.; Mohammed Khan K.
author_sort Taha M.; Sultan S.; Imran S.; Rahim F.; Zaman K.; Wadood A.; Ur Rehman A.; Uddin N.; Mohammed Khan K.
title Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies
title_short Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies
title_full Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies
title_fullStr Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies
title_full_unstemmed Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies
title_sort Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies
publishDate 2019
container_title Bioorganic and Medicinal Chemistry
container_volume 27
container_issue 18
doi_str_mv 10.1016/j.bmc.2019.07.035
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85069971619&doi=10.1016%2fj.bmc.2019.07.035&partnerID=40&md5=6c1dae4e50ca9d71d8e319c5e61a39dc
description In searchof the potenttherapeutic agent as an α-glucosidase inhibitor, we have synthesized twenty-five analogs (1–25) of quinoline-based Schiff bases as an inhibitoragainst α-glucosidase enzyme under positive control acarbose (IC50 = 38.45 ± 0.80 µM). From the activity profile it was foundthat analogs 1, 2, 3, 4, 11, 12 and 20with IC50values 12.40 ± 0.40, 9.40 ± 0.30, 14.10 ± 0.40, 6.20 ± 0.30, 14.40 ± 0.40, 7.40 ± 0.20 and 13.20 ± 0.40 µMrespectively showed most potent inhibition among the series even than standard drug acarbose (IC50 = 38.45 ± 0.80 µM). Here in the present study analog 4 (IC50 = 6.20 ± 0.30 µM) was found with many folds better α-glucosidase inhibitory activity than the reference drug. Eight analogs like 5, 7, 8, 16, 17, 22, 24 and 25 among the whole series displayed less than 50% inhibition. The substituents effects on phenyl ring thereby superficially established through SAR study. Binding interactions of analogs and the active site of ligands proteins were confirmed through molecular docking study. Spectroscopic techniques like 1H NMR, 13C NMR and ESIMS were used for characterization. © 2019 Elsevier Ltd
publisher Elsevier Ltd
issn 9680896
language English
format Article
accesstype
record_format scopus
collection Scopus
_version_ 1809678482779668480

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