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4H-benzochromene derivatives as novel tyrosinase inhibitors and radical scavengers: synthesis, biological evaluation, and molecular docking analysis.
Mol Divers. 2020 Jul 18 [Online ahead of print]MD

Abstract

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.

Authors+Show Affiliations

Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran.Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran.Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran.Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran.Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran.Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran.Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran. m.khoshneviszadeh@gmail.com. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran. m.khoshneviszadeh@gmail.com.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32683615

Citation

Karimian, Somaye, et al. "4H-benzochromene Derivatives as Novel Tyrosinase Inhibitors and Radical Scavengers: Synthesis, Biological Evaluation, and Molecular Docking Analysis." Molecular Diversity, 2020.
Karimian S, Ranjbar S, Dadfar M, et al. 4H-benzochromene derivatives as novel tyrosinase inhibitors and radical scavengers: synthesis, biological evaluation, and molecular docking analysis. Mol Divers. 2020.
Karimian, S., Ranjbar, S., Dadfar, M., Khoshneviszadeh, M., Gholampour, M., Sakhteman, A., & Khoshneviszadeh, M. (2020). 4H-benzochromene derivatives as novel tyrosinase inhibitors and radical scavengers: synthesis, biological evaluation, and molecular docking analysis. Molecular Diversity. https://doi.org/10.1007/s11030-020-10123-0
Karimian S, et al. 4H-benzochromene Derivatives as Novel Tyrosinase Inhibitors and Radical Scavengers: Synthesis, Biological Evaluation, and Molecular Docking Analysis. Mol Divers. 2020 Jul 18; PubMed PMID: 32683615.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 4H-benzochromene derivatives as novel tyrosinase inhibitors and radical scavengers: synthesis, biological evaluation, and molecular docking analysis. AU - Karimian,Somaye, AU - Ranjbar,Sara, AU - Dadfar,Mahsa, AU - Khoshneviszadeh,Mahsima, AU - Gholampour,Maryam, AU - Sakhteman,Amirhossein, AU - Khoshneviszadeh,Mehdi, Y1 - 2020/07/18/ PY - 2019/09/24/received PY - 2020/07/02/accepted PY - 2020/7/20/entrez PY - 2020/7/20/pubmed PY - 2020/7/20/medline KW - 2-Amino-4-phenyl-4H-benzo[h]chromene-3-carboxylate KW - Chromene KW - Diphenolase inhibitory activity KW - Melanin KW - Mushroom tyrosianse JF - Molecular diversity JO - Mol. Divers. N2 - 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. SN - 1573-501X UR - https://www.unboundmedicine.com/medline/citation/32683615/4H_benzochromene_derivatives_as_novel_tyrosinase_inhibitors_and_radical_scavengers:_synthesis_biological_evaluation_and_molecular_docking_analysis_ L2 - https://doi.org/10.1007/s11030-020-10123-0 DB - PRIME DP - Unbound Medicine ER -
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