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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2020
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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 |
_version_ |
1809677598859460608 |