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 & biodiversity 2024-04, Vol.21 (4), p.e202400133-n/a
Main Authors: Zeb, Aurang, Abbasi, Muhammad Athar, Aziz‐ur‐Rehman, Siddiqui, Sabahat Zahra, Hassan, Mubashir, Javed, Qamar, Rafiq, Muhammad, Ali, Anser, Shah, Syed Adnan Ali, Kloczkowski, Andrzej
Format: Article
Language:English
Subjects:
1-Phenylpiperazine
3-substituted-benzamides
Aromatic compounds
Chemical synthesis
Docking
Energy value
Kinetics
Ligands
Molecular docking
NMR
Nuclear magnetic resonance
Skin diseases
Substitutes
Tyrosinase
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Summary: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.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.202400133