SÍNTESE E AVALIAÇÃO DAS ATIVIDADES FOTOPROTETORA, CITOTÓXICA E ANTIVIRAL CONTRA O ZIKA VÍRUS DE DERIVADOS TRIAZÓLICOS DA BENZOFENONA

• Published in: Química Nova Vol. 42; no. 5; pp. 473 - 484
• Main Authors: Ângela M. A. Lima, Róbson R. Teixeira, Bianca F. da Silva, Raoni P. Siqueira, Ítalo E. P. da Silva, Edjon G. Santos, Maria Cecília Fernandes, Victor Hugo Sousa Gonçalves, Gustavo C. Bressan, Tiago Antonio de Oliveira Mendes, Sérgio O. de Paula, Adílson Vidal Costa, Marcelo H. dos Santos
• Format: Journal Article
• Language: English
• Published: Sociedade Brasileira de Química
• Subjects: 1,2,3-triazole; antiviral; benzophenone; cytotoxicity; photoprotective activity
• ISSN: 1678-7064
• DOI: 10.21577/0100-4042.20170365

The benzophenones are synthetic and natural compounds presenting a variety of activities, including photoprotective, cytotoxic and antiviral. It is herein described the preparation of a series of twenty-seven benzophenone derivatives bearing 1,2,3-triazole functionalities and the evaluation of their photoprotective, cytotoxic and antiviral on Zika Virus (ZIKV) activities. The compounds were prepared in three steps, namely reduction of benzophenone, alkylation of diphenylmethanol and CuAAC reactions. The in vitro evaluation of the photoprotective activity revealed that the most active derivative 4-((benzhydryloxy)methyl)-1-(4-nitrobenzyl)-1H-1,2,3-triazole (4k) displayed UVB sun protection factor equal to 6,9±0,53, which make this compound a possible candidate to be used in formulations for photoprotective applications. In terms of cytotoxicity, the compounds were evaluated against MDA-MB-231 and B16F10 cell lines. It was observed that the compounds were more active against MDA-MB-231 cells and three of them were capable of reducing cell viability by approximately 55% at 100 µmol L-1. In the antiviral screening against ZIKV, compound 4-(3-benzhydryloxy)propyl)-1-(3-methylbenzyl)-1H-1,2,3-triazole (5j) was the most effective in mantaining Vero cell viability.