Synthesis of dihydropyranocarbonitrile compounds based on kojic acid linked to 1,2,3-triazole ring by click chemistry approach and their evaluation as potential tyrosinase inhibitors

Subject Areas : شیمی آلی

Zahra Najafi ¹ , Soheila Esmaili ² , Saeed Babaee ³ , Behnam Khaleseh ⁴ , Gholamabbas Chehardoli ⁵ , Mehdi Khoshneviszadeh ⁶ , Tahmineh Akbarzadeh ⁷

1 - Department of Medicinal Chemistry, School of Pharmacy, Hamadan University of Medical Sciences, Hamadan, Iran
2 - Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran
3 - Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran
4 - Department of Medicinal Chemistry, School of Pharmacy, Hamadan University of Medical Sciences, Hamadan, Iran
5 - Department of Medicinal Chemistry, School of Pharmacy, Hamadan University of Medical Sciences, Hamadan, Iran
6 - Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
7 - Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Received: 2023-01-12 Accepted : 2023-02-05 Published : 2023-02-20

Keywords: 2, 1, Cyclization, Molecular docking, Kojic acid, 3-Triazole, Tyrosinase inhibitors,

Abstract :

In this research, synthesis of dihydropyranocarbonitrile compounds based on kojic acid linked to 1,2,3-triazole ring were performed by click chemistry method and evaluated as tyrosinase enzyme. Ring formation of triazole in the target compounds was performed by the classic Sharpless approach and in the presence of copper as catalyst. The compounds included three categories including kojic acid derivatives with 1,2,3-triazole ring based on 4-hydroxybenzaldehyde, 3-hydroxybenzaldehyde, and 4-hydroxy-3-methoxy benzaldehyde (vanillin). In vitro evaluation of the tyrosinase enzyme inhibitory effect of all compounds was performed. Most of the compounds showed moderate to weak inhibition and finally, the results were reported as inhibition percentage. Among them 8d, 8f, and 8n compounds have the best percentage of tyrosinase enzyme inhibitory activity with percentages of 40.40 ± 2.88, 45.53 ± 3.05, and 42.52 ± 2.05, respectively, compared to kojic acid as standard control (19.69 ± 2.11 μM). Docking studies showed that the compounds interacted with the amino acids of the entry of active site and its around. In addition, the drug-likeness and pharmacokinetic properties for the selected compounds were calculated and the obtained data were within the acceptable range.

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