Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors

Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors

This manuscript describes the synthesis of some new N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides (5a-c) through a facile bi-step strategy. The structures of these compounds were corroborated by their IR, EI-MS, 1H NMR, 13C NMR spectra along with CHN analysis data. The results of Mush...

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Published in:Journal of Molecular Structure
Main Author: Raza H.; Abbasi M.A.; Rehman A.-U.; Siddiqui S.Z.; Hassan M.; Shah S.A.A.; Shahid M.; Hong H.; Seo S.-Y.
Format: Article
Language:English
Published: Elsevier B.V. 2020
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85081681057&doi=10.1016%2fj.molstruc.2020.127969&partnerID=40&md5=edf68b9124e195ebc612a7af38410c4f
id 2-s2.0-85081681057
spelling 2-s2.0-85081681057
Raza H.; Abbasi M.A.; Rehman A.-U.; Siddiqui S.Z.; Hassan M.; Shah S.A.A.; Shahid M.; Hong H.; Seo S.-Y.
Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors
2020
Journal of Molecular Structure
1210

10.1016/j.molstruc.2020.127969
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85081681057&doi=10.1016%2fj.molstruc.2020.127969&partnerID=40&md5=edf68b9124e195ebc612a7af38410c4f
This manuscript describes the synthesis of some new N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides (5a-c) through a facile bi-step strategy. The structures of these compounds were corroborated by their IR, EI-MS, 1H NMR, 13C NMR spectra along with CHN analysis data. The results of Mushroom tyrosinase in vitro inhibition revealed that all compounds were superb inhibitors of this enzyme and among them 5b was identified as the most active compound having IC50 value of 0.168 ± 0.057 μM, relative to the standard (16.841 ± 1.146 μM). The kinetic analysis (Ki = 0.22 μM) of this molecule revealed that it does not competitively inhibit the tyrosinase enzyme. It also significantly reduced (P < 0.001) the enormous amount of pigments to about 75.373% in an in vivo protocol, when studied on the zebrafish embryos. Moreover, the cytotoxicity of these butanamides was also profiled and it was an inferred that of these molecules possess very mild cytotoxicity. So, it was consummated from the present investigation that these compounds might be utilized as less cytotoxic therapeutic agents for the betterment of skin related ailments. © 2020
Elsevier B.V.
222860
English
Article
author Raza H.; Abbasi M.A.; Rehman A.-U.; Siddiqui S.Z.; Hassan M.; Shah S.A.A.; Shahid M.; Hong H.; Seo S.-Y.
spellingShingle Raza H.; Abbasi M.A.; Rehman A.-U.; Siddiqui S.Z.; Hassan M.; Shah S.A.A.; Shahid M.; Hong H.; Seo S.-Y.
Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors
author_facet Raza H.; Abbasi M.A.; Rehman A.-U.; Siddiqui S.Z.; Hassan M.; Shah S.A.A.; Shahid M.; Hong H.; Seo S.-Y.
author_sort Raza H.; Abbasi M.A.; Rehman A.-U.; Siddiqui S.Z.; Hassan M.; Shah S.A.A.; Shahid M.; Hong H.; Seo S.-Y.
title Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors
title_short Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors
title_full Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors
title_fullStr Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors
title_full_unstemmed Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors
title_sort Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors
publishDate 2020
container_title Journal of Molecular Structure
container_volume 1210
container_issue
doi_str_mv 10.1016/j.molstruc.2020.127969
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85081681057&doi=10.1016%2fj.molstruc.2020.127969&partnerID=40&md5=edf68b9124e195ebc612a7af38410c4f
description This manuscript describes the synthesis of some new N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides (5a-c) through a facile bi-step strategy. The structures of these compounds were corroborated by their IR, EI-MS, 1H NMR, 13C NMR spectra along with CHN analysis data. The results of Mushroom tyrosinase in vitro inhibition revealed that all compounds were superb inhibitors of this enzyme and among them 5b was identified as the most active compound having IC50 value of 0.168 ± 0.057 μM, relative to the standard (16.841 ± 1.146 μM). The kinetic analysis (Ki = 0.22 μM) of this molecule revealed that it does not competitively inhibit the tyrosinase enzyme. It also significantly reduced (P < 0.001) the enormous amount of pigments to about 75.373% in an in vivo protocol, when studied on the zebrafish embryos. Moreover, the cytotoxicity of these butanamides was also profiled and it was an inferred that of these molecules possess very mild cytotoxicity. So, it was consummated from the present investigation that these compounds might be utilized as less cytotoxic therapeutic agents for the betterment of skin related ailments. © 2020
publisher Elsevier B.V.
issn 222860
language English
format Article
accesstype
record_format scopus
collection Scopus
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