Synthesis, biological evaluation and molecular docking analysis of vaniline–benzylidenehydrazine hybrids as potent tyrosinase inhibitors

In this work, 11 novel compounds based on vaniline and benzylidenehydrazine structure were synthesized with various substituents on phenyl aromatic ring of the molecule and evaluated as tyrosinase inhibitors. These new derivatives showed significant anti-tyrosinase activities, among which 4i demonst...

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Autores principales: Iraji, Aida, Adelpour, Tina, Edraki, Najmeh, Khoshneviszadeh, Mahsima, Miri, Ramin, Khoshneviszadeh, Mehdi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2020
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7137441/
https://www.ncbi.nlm.nih.gov/pubmed/32280949
http://dx.doi.org/10.1186/s13065-020-00679-1
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author Iraji, Aida
Adelpour, Tina
Edraki, Najmeh
Khoshneviszadeh, Mahsima
Miri, Ramin
Khoshneviszadeh, Mehdi
author_facet Iraji, Aida
Adelpour, Tina
Edraki, Najmeh
Khoshneviszadeh, Mahsima
Miri, Ramin
Khoshneviszadeh, Mehdi
author_sort Iraji, Aida
collection PubMed
description In this work, 11 novel compounds based on vaniline and benzylidenehydrazine structure were synthesized with various substituents on phenyl aromatic ring of the molecule and evaluated as tyrosinase inhibitors. These new derivatives showed significant anti-tyrosinase activities, among which 4i demonstrated to be the most potent compound, with IC(50) values of 1.58 µM . The structure–activity relationship study of the novel constructed analogs was fully discussed. Kinetic study of compound 4i showed uncompetitive inhibition towards tyrosinase. Furthermore, the high potency of 4i was supported theoretically by molecular docking evaluations. [Image: see text]
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spelling pubmed-71374412020-04-11 Synthesis, biological evaluation and molecular docking analysis of vaniline–benzylidenehydrazine hybrids as potent tyrosinase inhibitors Iraji, Aida Adelpour, Tina Edraki, Najmeh Khoshneviszadeh, Mahsima Miri, Ramin Khoshneviszadeh, Mehdi BMC Chem Research Article In this work, 11 novel compounds based on vaniline and benzylidenehydrazine structure were synthesized with various substituents on phenyl aromatic ring of the molecule and evaluated as tyrosinase inhibitors. These new derivatives showed significant anti-tyrosinase activities, among which 4i demonstrated to be the most potent compound, with IC(50) values of 1.58 µM . The structure–activity relationship study of the novel constructed analogs was fully discussed. Kinetic study of compound 4i showed uncompetitive inhibition towards tyrosinase. Furthermore, the high potency of 4i was supported theoretically by molecular docking evaluations. [Image: see text] Springer International Publishing 2020-04-07 /pmc/articles/PMC7137441/ /pubmed/32280949 http://dx.doi.org/10.1186/s13065-020-00679-1 Text en © The Author(s) 2020 Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated in a credit line to the data.
spellingShingle Research Article
Iraji, Aida
Adelpour, Tina
Edraki, Najmeh
Khoshneviszadeh, Mahsima
Miri, Ramin
Khoshneviszadeh, Mehdi
Synthesis, biological evaluation and molecular docking analysis of vaniline–benzylidenehydrazine hybrids as potent tyrosinase inhibitors
title Synthesis, biological evaluation and molecular docking analysis of vaniline–benzylidenehydrazine hybrids as potent tyrosinase inhibitors
title_full Synthesis, biological evaluation and molecular docking analysis of vaniline–benzylidenehydrazine hybrids as potent tyrosinase inhibitors
title_fullStr Synthesis, biological evaluation and molecular docking analysis of vaniline–benzylidenehydrazine hybrids as potent tyrosinase inhibitors
title_full_unstemmed Synthesis, biological evaluation and molecular docking analysis of vaniline–benzylidenehydrazine hybrids as potent tyrosinase inhibitors
title_short Synthesis, biological evaluation and molecular docking analysis of vaniline–benzylidenehydrazine hybrids as potent tyrosinase inhibitors
title_sort synthesis, biological evaluation and molecular docking analysis of vaniline–benzylidenehydrazine hybrids as potent tyrosinase inhibitors
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7137441/
https://www.ncbi.nlm.nih.gov/pubmed/32280949
http://dx.doi.org/10.1186/s13065-020-00679-1
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