4H-benzochromene derivatives as novel tyrosinase inhibitors and radical scavengers: synthesis, biological evaluation, and molecular docking analysis
| Autor: | Amirhossein Sakhteman, Mahsima Khoshneviszadeh, Sara Ranjbar, Maryam Gholampour, Somaye Karimian, Mehdi Khoshneviszadeh, Mahsa Dadfar |
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| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Chemistry Monophenol Monooxygenase In silico Tyrosinase Organic Chemistry Molecular Docking Analysis General Medicine 010402 general chemistry Ring (chemistry) 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Inorganic Chemistry Melanin Drug Discovery Physical and Theoretical Chemistry Binding site Molecular Biology Information Systems Biological evaluation ADME |
| Zdroj: | Molecular diversity. 25(4) |
| ISSN: | 1573-501X |
| Popis: | A series of ethyl 2-amino-4H-benzo[h]chromene-3-carboxylate derivatives, having phenyl ring with diverse substituents at C4 position of 4H-benzochromene nucleus, were synthesized via one-pot three-component reaction between various aromatic aldehydes, α-naphthol, and ethyl cyanoacetate. The synthesized compounds were screened for their antityrosinase activity. Compound 4i, bearing 4-dimethylamino substitution on C4-phenyl ring, was the most potent tyrosinase inhibitor (IC50 = 34.12 μM). The inhibition kinetic analysis of 4i indicated that the compound was a competitive tyrosinase inhibitor. Compounds 4a, 4g, 4i and 4j were the effective radical scavengers with EC50s in the range of 0.144–0.943 mM. According to the in silico drug-like and ADME predictions, 4i can be considered as a suitable candidate. Molecular docking results confirmed that the derivative was well accommodated within the mushroom tyrosinase binding site. Therefore, 4i can be introduced as a novel tyrosinase inhibitor that might be a promising lead in medicine, cosmetics, and food industry. |
| Databáze: | OpenAIRE |
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