Synthesis of 1,2,3-Triazole Derivatives of 4,4'-Dihydroxybenzophenone and Evaluation of Their Elastase Inhibitory Activity

AUTOR(ES)

Dias, Maria C. F.

FONTE

J. Braz. Chem. Soc.

DATA DE PUBLICAÇÃO

2019-01

RESUMO

The present investigation describes the synthesis of a series of novel triazole derivatives from 4,4'-dihydroxybenzophenone along with their elastase inhibitory activity. The 1,2,3-triazoles were obtained via the copper(I)-catalyzed azide-alkyne cycloaddition reaction (CuAAC), also known as click reaction, between bis(4-(prop-2-yn-1-yloxy))benzophenone and several benzyl azides. It was found that five derivatives exhibited significant inhibitory effects, presenting half maximal inhibitory concentration (IC50) values in the range of 16.6 to 72.1 µM. The most active compound, namely bis(4-(1-(4-iodobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)benzophenone (IC50 = 16.6 ± 1.9 µM), was found to bind to elastase with the inhibition constant (Ki) of 11.12 µM, thereby illustrating competitive inhibitory behavior. Further, docking investigations provided insights on the possible binding mode of the most active compound with the elastase.

Documentos Relacionados

• Synthesis and phytotoxic activity of 1,2,3-triazole derivatives
• Synthesis and Evaluation of Antibacterial Activity of 1,2,3-Triazole and Ether Derivatives of Paeonol
• Synthesis by Click Reactions and Antiplasmodial Activity of Lupeol 1,2,3-Triazole Derivatives
• Synthesis of Nerol Derivatives Containing a 1,2,3-Triazole Moiety and Evaluation of Their Activities against Cancer Cell Lines
• Synthesis of 1,2,3-Triazole Derivatives of Hydnocarpic Acid Isolated from Carpotroche brasiliensis Seed Oil and Evaluation of Antiproliferative Activity