Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors

Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors

In the aimed research study, a new series of N-(aryl)-3-[(4-phenyl-1-piperazinyl)methyl]benzamides was synthesized, which was envisaged as tyrosinase inhibitor. The structures of these newly designed molecules were verified by IR, 1H-NMR, 13C-NMR, EI-MS and CHN analysis data. These molecules were sc...

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Published in:Chemistry and Biodiversity
Main Author: Zeb A.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Hassan M.; Javed Q.; Rafiq M.; Ali A.; Shah S.A.A.; Kloczkowski A.
Format: Article
Language:English
Published: John Wiley and Sons Inc 2024
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85187520882&doi=10.1002%2fcbdv.202400133&partnerID=40&md5=169ecb59a6d33844025e81915c3b2f9d
id 2-s2.0-85187520882
spelling 2-s2.0-85187520882
Zeb A.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Hassan M.; Javed Q.; Rafiq M.; Ali A.; Shah S.A.A.; Kloczkowski A.
Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors
2024
Chemistry and Biodiversity
21
4
10.1002/cbdv.202400133
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85187520882&doi=10.1002%2fcbdv.202400133&partnerID=40&md5=169ecb59a6d33844025e81915c3b2f9d
In the aimed research study, a new series of N-(aryl)-3-[(4-phenyl-1-piperazinyl)methyl]benzamides was synthesized, which was envisaged as tyrosinase inhibitor. The structures of these newly designed molecules were verified by IR, 1H-NMR, 13C-NMR, EI-MS and CHN analysis data. These molecules were screened against tyrosinase and their inhibitory activity explored that these 3-substituted-benzamides exhibit good to excellent potential, comparative to the standard. The Kinetics mechanism was investigated through Lineweaver-Burk plots which depicted that molecules inhibited this enzyme in a competitive mode. Moreover, molecular docking was also performed to determine the binding interaction of all synthesized molecules (ligands) with the active site of tyrosinase enzyme and the results showed that most of the ligands exhibited efficient binding energy values. Therefore, it is anticipated that these molecules might serve as auspicious therapeutic scaffolds for treatment of the tyrosinase associated skin disorders. © 2024 Wiley-VHCA AG, Zurich, Switzerland.
John Wiley and Sons Inc
16121872
English
Article
author Zeb A.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Hassan M.; Javed Q.; Rafiq M.; Ali A.; Shah S.A.A.; Kloczkowski A.
spellingShingle Zeb A.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Hassan M.; Javed Q.; Rafiq M.; Ali A.; Shah S.A.A.; Kloczkowski A.
Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors
author_facet Zeb A.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Hassan M.; Javed Q.; Rafiq M.; Ali A.; Shah S.A.A.; Kloczkowski A.
author_sort Zeb A.; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Hassan M.; Javed Q.; Rafiq M.; Ali A.; Shah S.A.A.; Kloczkowski A.
title Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors
title_short Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors
title_full Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors
title_fullStr Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors
title_full_unstemmed Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors
title_sort Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors
publishDate 2024
container_title Chemistry and Biodiversity
container_volume 21
container_issue 4
doi_str_mv 10.1002/cbdv.202400133
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85187520882&doi=10.1002%2fcbdv.202400133&partnerID=40&md5=169ecb59a6d33844025e81915c3b2f9d
description In the aimed research study, a new series of N-(aryl)-3-[(4-phenyl-1-piperazinyl)methyl]benzamides was synthesized, which was envisaged as tyrosinase inhibitor. The structures of these newly designed molecules were verified by IR, 1H-NMR, 13C-NMR, EI-MS and CHN analysis data. These molecules were screened against tyrosinase and their inhibitory activity explored that these 3-substituted-benzamides exhibit good to excellent potential, comparative to the standard. The Kinetics mechanism was investigated through Lineweaver-Burk plots which depicted that molecules inhibited this enzyme in a competitive mode. Moreover, molecular docking was also performed to determine the binding interaction of all synthesized molecules (ligands) with the active site of tyrosinase enzyme and the results showed that most of the ligands exhibited efficient binding energy values. Therefore, it is anticipated that these molecules might serve as auspicious therapeutic scaffolds for treatment of the tyrosinase associated skin disorders. © 2024 Wiley-VHCA AG, Zurich, Switzerland.
publisher John Wiley and Sons Inc
issn 16121872
language English
format Article
accesstype
record_format scopus
collection Scopus
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