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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Published inBMC chemistry Vol. 14; no. 1; p. 28
Main Authors Iraji, Aida, Adelpour, Tina, Edraki, Najmeh, Khoshneviszadeh, Mahsima, Miri, Ramin, Khoshneviszadeh, Mehdi
Format Journal Article
LanguageEnglish
Published Cham Springer International Publishing 07.04.2020
Springer Nature B.V
BMC
Subjects
Anti-tyrosinase agents
Aromatic compounds
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inhibitors
Kinetic study
Medicinal Chemistry
Methoxybenzohydrazide
Molecular docking
Research Article
Structure-based design
Tyrosinase
Kinetic study
Methoxybenzohydrazide
Anti-tyrosinase agents
Structure-based design
Molecular docking
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Summary: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.
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ISSN:2661-801X
2661-801X
DOI:10.1186/s13065-020-00679-1