Synthesis of Carbazole–Thiazole Dyes via One-Pot Tricomponent Reaction: Exploring Photophysical Properties, Tyrosinase Inhibition, and Molecular Docking

Autor: Przemysław Krawczyk, Beata Jędrzejewska, Joanna Cytarska, Klaudia Seklecka, Krzysztof Z. Łączkowski
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Sensors, Vol 24, Iss 19, p 6368 (2024)
Druh dokumentu: article
ISSN: 1424-8220
DOI: 10.3390/s24196368
Popis: Carbazole is an aromatic heterocyclic organic compound consisting of two fused benzene rings and a pyrrole ring and is a very valuable building structure for the design of many compounds for use in various fields of chemistry and medicine. This study presents three new carbazole-based thiazole derivatives that differ in the presence of a different halogen atom: chlorine, bromine, and fluorine. Experimental studies and quantum-chemical simulations show the effect of changing a halogen atom on the physicochemical, biological, and linear and nonlinear optical properties. We have also found that carbazoles C-Cl, C-Br, and C-F exhibit high tyrosinase inhibitory activity, with IC50 values in the range of 68–105 µM with mixed mechanism of action. Finally, molecular docking to the active site of Concanavalin A (ConA) and bioavailability for all compounds were evaluated.
Databáze: Directory of Open Access Journals
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