Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions

Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions

In the study presented here, novel bioactive series of indole-N-ethyltriazole hybrids was synthesized and structures of these hybrid molecules (9a-h) were corroborated by IR, 1H-NMR, 13C-NMR, EI-MS and CHN analysis data. The in vitro studies of these multi-functional molecules demonstrated their pot...

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Published in:Journal of Molecular Structure
Main Author: Shakila; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Nazir M.; Raza H.; Zafar A.; Shah S.A.A.; Shahid M.; Seo S.-Y.
Format: Article
Language:English
Published: Elsevier B.V. 2022
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85127463628&doi=10.1016%2fj.molstruc.2022.132953&partnerID=40&md5=a567d0d1dd7289e4bc0c51a9dcf8ddab
id 2-s2.0-85127463628
spelling 2-s2.0-85127463628
Shakila; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Nazir M.; Raza H.; Zafar A.; Shah S.A.A.; Shahid M.; Seo S.-Y.
Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions
2022
Journal of Molecular Structure
1261

10.1016/j.molstruc.2022.132953
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85127463628&doi=10.1016%2fj.molstruc.2022.132953&partnerID=40&md5=a567d0d1dd7289e4bc0c51a9dcf8ddab
In the study presented here, novel bioactive series of indole-N-ethyltriazole hybrids was synthesized and structures of these hybrid molecules (9a-h) were corroborated by IR, 1H-NMR, 13C-NMR, EI-MS and CHN analysis data. The in vitro studies of these multi-functional molecules demonstrated their potent tyrosinase inhibition relative to the standard used and all the synthesized compounds showed mild hemolysis. The kinetics mechanism was exposed by lineweaver-burk plots which revealed that, 9c, inhibited tyrosinase non-competitively by forming an enzyme-inhibitor complex. So, it was summated that these hybrid molecules might lead to further research gateways for obtaining better and safe therapeutic agents for skin pigmentation and related ailments. © 2022
Elsevier B.V.
222860
English
Article
author Shakila; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Nazir M.; Raza H.; Zafar A.; Shah S.A.A.; Shahid M.; Seo S.-Y.
spellingShingle Shakila; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Nazir M.; Raza H.; Zafar A.; Shah S.A.A.; Shahid M.; Seo S.-Y.
Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions
author_facet Shakila; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Nazir M.; Raza H.; Zafar A.; Shah S.A.A.; Shahid M.; Seo S.-Y.
author_sort Shakila; Abbasi M.A.; Aziz-ur-Rehman; Siddiqui S.Z.; Nazir M.; Raza H.; Zafar A.; Shah S.A.A.; Shahid M.; Seo S.-Y.
title Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions
title_short Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions
title_full Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions
title_fullStr Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions
title_full_unstemmed Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions
title_sort Multi-step synthesis of indole-N-ethyltriazole hybrids amalgamated with N-arylated ethanamides: structure-activity relationship and mechanistic explorations through tyrosinase inhibition, kinetics and computational ascriptions
publishDate 2022
container_title Journal of Molecular Structure
container_volume 1261
container_issue
doi_str_mv 10.1016/j.molstruc.2022.132953
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85127463628&doi=10.1016%2fj.molstruc.2022.132953&partnerID=40&md5=a567d0d1dd7289e4bc0c51a9dcf8ddab
description In the study presented here, novel bioactive series of indole-N-ethyltriazole hybrids was synthesized and structures of these hybrid molecules (9a-h) were corroborated by IR, 1H-NMR, 13C-NMR, EI-MS and CHN analysis data. The in vitro studies of these multi-functional molecules demonstrated their potent tyrosinase inhibition relative to the standard used and all the synthesized compounds showed mild hemolysis. The kinetics mechanism was exposed by lineweaver-burk plots which revealed that, 9c, inhibited tyrosinase non-competitively by forming an enzyme-inhibitor complex. So, it was summated that these hybrid molecules might lead to further research gateways for obtaining better and safe therapeutic agents for skin pigmentation and related ailments. © 2022
publisher Elsevier B.V.
issn 222860
language English
format Article
accesstype
record_format scopus
collection Scopus
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