Síntese E Avaliação Das Atividades Fotoprotetora, Citotóxica E Antiviral Contra O Zika Vírus De Derivados Triazólicos Da Benzofenona

Abstract

SYNTHESIS AND EVALUATION OF THE PHOTOPROTECTIVE, CYTOTOXIC AND ANTIVIRAL ACTIVITY OF BENZOPHENONE DERIVATIVES CONTAINING 1,2,3-TRIAZOLIC PORTIONS. 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-1,2,3triazole (5j) was the most effective in mantaining Vero cell viability.

Searching Anti-Zika Virus Activity in 1H-1,2,3-Triazole Based Compounds

“…Lima’s triazole series showed high cytotoxicity. The antiviral activity were the best ZIKV inhibitors, considering at least 50% of cell viability [ 22 ].…”

“…These three classes of compounds, namely 1,4-naphthoquinone, phthalimide and 1,2,3-triazole inspired our research. These moieties have biological activities against several infections [18][19][20], including ZIKV [21,22]. Our group has synthesized several heterocycle derivatives and tested their activities against human cancer cell lines [23][24][25].…”

Triazole derivatives of guttiferone-A inhibit the proliferation of HepG2 cells by modulating MAPK/ERK signaling and expression profiles of regulators of G1/S transition

“…5 Benzophenones (BZPs) are a class of natural compounds that have attracted the interest of many researchers due to their pharmacological properties. [6][7][8] BZPs and their derivatives display antimicrobial, [9][10][11] anti-inflammatory, 12 antiviral, 13,14 antioxidant, 10,15 and anticancer properties. [16][17][18][19][20] The prenylated BZPs guttiferone-A (G-A) and 7-epiclusianone (7-epi) (Fig.…”