Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α-Naphthalene-Containing Alkyl Phenyl Ether Fragment as Potent α-Amylase and α-Glucosidase Inhibitors

Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α-Naphthalene-Containing Alkyl Phenyl Ether Fragment as Potent α-Amylase and α-Glucosidase Inhibitors

In this study, new Schiff base derivatives of α-naphthalene acetic acid containing alkyl phenyl ether fragment have been effectively synthesized through multistep reaction process, characterized by 1H-NMR and 13C-NMR spectroscopy. These derivatives have been tested for their in vitro α-amylase and α...

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Published in:ChemistrySelect
Main Author: Shah T.A.; Alam A.; Zainab; Assad M.; Parveen Z.; Rafiq H.; Ayaz M.; Shah S.A.A.; Latif A.; Ali M.; Ahmad M.
Format: Article
Language:English
Published: John Wiley and Sons Inc 2024
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85208551606&doi=10.1002%2fslct.202402297&partnerID=40&md5=7529a46cdd58ade447402d91f199e325
id 2-s2.0-85208551606
spelling 2-s2.0-85208551606
Shah T.A.; Alam A.; Zainab; Assad M.; Parveen Z.; Rafiq H.; Ayaz M.; Shah S.A.A.; Latif A.; Ali M.; Ahmad M.
Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α-Naphthalene-Containing Alkyl Phenyl Ether Fragment as Potent α-Amylase and α-Glucosidase Inhibitors
2024
ChemistrySelect
9
42
10.1002/slct.202402297
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85208551606&doi=10.1002%2fslct.202402297&partnerID=40&md5=7529a46cdd58ade447402d91f199e325
In this study, new Schiff base derivatives of α-naphthalene acetic acid containing alkyl phenyl ether fragment have been effectively synthesized through multistep reaction process, characterized by 1H-NMR and 13C-NMR spectroscopy. These derivatives have been tested for their in vitro α-amylase and α-glucosidase inhibitory activities. In the series, 8 compounds (2j, 2f, 2e, 2m, 2a, 2b, 2l, and 2c) exhibited promising α-amylase inhibition with IC50 values from 5.38 ± 0.36 to 14.59 ± 0.64 µg/mL. Similarly, in the case of α-glucosidase inhibitory activity, 10 derivatives (2e, 2f, 2j, 2m, 2b, 2c, 2i, 2d, 2a, and 2l) exhibited excellent activity having IC50 values from 6.96 ± 0.39 to 16.27 ± 0.31 µg/mL, wheras the remaining derivatives exhibited good-to-least antidiabetic potential. The ADME properties were calculated for all Schiff base derivatives using Swiss-ADME web tool. Furthermore, the docking studies identified the binding modes of the compounds. © 2024 Wiley-VCH GmbH.
John Wiley and Sons Inc
23656549
English
Article
author Shah T.A.; Alam A.; Zainab; Assad M.; Parveen Z.; Rafiq H.; Ayaz M.; Shah S.A.A.; Latif A.; Ali M.; Ahmad M.
spellingShingle Shah T.A.; Alam A.; Zainab; Assad M.; Parveen Z.; Rafiq H.; Ayaz M.; Shah S.A.A.; Latif A.; Ali M.; Ahmad M.
Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α-Naphthalene-Containing Alkyl Phenyl Ether Fragment as Potent α-Amylase and α-Glucosidase Inhibitors
author_facet Shah T.A.; Alam A.; Zainab; Assad M.; Parveen Z.; Rafiq H.; Ayaz M.; Shah S.A.A.; Latif A.; Ali M.; Ahmad M.
author_sort Shah T.A.; Alam A.; Zainab; Assad M.; Parveen Z.; Rafiq H.; Ayaz M.; Shah S.A.A.; Latif A.; Ali M.; Ahmad M.
title Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α-Naphthalene-Containing Alkyl Phenyl Ether Fragment as Potent α-Amylase and α-Glucosidase Inhibitors
title_short Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α-Naphthalene-Containing Alkyl Phenyl Ether Fragment as Potent α-Amylase and α-Glucosidase Inhibitors
title_full Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α-Naphthalene-Containing Alkyl Phenyl Ether Fragment as Potent α-Amylase and α-Glucosidase Inhibitors
title_fullStr Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α-Naphthalene-Containing Alkyl Phenyl Ether Fragment as Potent α-Amylase and α-Glucosidase Inhibitors
title_full_unstemmed Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α-Naphthalene-Containing Alkyl Phenyl Ether Fragment as Potent α-Amylase and α-Glucosidase Inhibitors
title_sort Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α-Naphthalene-Containing Alkyl Phenyl Ether Fragment as Potent α-Amylase and α-Glucosidase Inhibitors
publishDate 2024
container_title ChemistrySelect
container_volume 9
container_issue 42
doi_str_mv 10.1002/slct.202402297
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85208551606&doi=10.1002%2fslct.202402297&partnerID=40&md5=7529a46cdd58ade447402d91f199e325
description In this study, new Schiff base derivatives of α-naphthalene acetic acid containing alkyl phenyl ether fragment have been effectively synthesized through multistep reaction process, characterized by 1H-NMR and 13C-NMR spectroscopy. These derivatives have been tested for their in vitro α-amylase and α-glucosidase inhibitory activities. In the series, 8 compounds (2j, 2f, 2e, 2m, 2a, 2b, 2l, and 2c) exhibited promising α-amylase inhibition with IC50 values from 5.38 ± 0.36 to 14.59 ± 0.64 µg/mL. Similarly, in the case of α-glucosidase inhibitory activity, 10 derivatives (2e, 2f, 2j, 2m, 2b, 2c, 2i, 2d, 2a, and 2l) exhibited excellent activity having IC50 values from 6.96 ± 0.39 to 16.27 ± 0.31 µg/mL, wheras the remaining derivatives exhibited good-to-least antidiabetic potential. The ADME properties were calculated for all Schiff base derivatives using Swiss-ADME web tool. Furthermore, the docking studies identified the binding modes of the compounds. © 2024 Wiley-VCH GmbH.
publisher John Wiley and Sons Inc
issn 23656549
language English
format Article
accesstype
record_format scopus
collection Scopus
_version_ 1820775431600603136

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