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Synthesis, structural and spectroscopic analysis, and antiproliferative activity of chalcone derivate (E)-1-(4-aminophenyl)-3-(benzo[b]thiophen-2-yl)prop‑2-en-1-one in Trypanosoma cruzi

2021; Elsevier BV; Volume: 1253; Linguagem: Inglês

10.1016/j.molstruc.2021.132197

1872-8014

Débora Hellen Almeida de Brito, Francisco Wagner Queiroz Almeida-Neto, Lyanna Rodrigues Ribeiro, Emanuel Paula Magalhães, Ramon Róseo Paula Pessoa Bezerra de Menezes, Tiago Lima Sampaio, Alice Maria Costa Martins, Paulo Nogueira Bandeira, Márcia Machado Marinho, Emmanuel Silva Marinho, Antônio C.H. Barreto, Pedro de Lima‐Neto, Gilberto D. Saraiva, Kirley Marques Canuto, Hélcio Silva dos Santos, Alexandre Magno Rodrigues Teixeira, Nágila Maria Pontes Silva Ricardo,

Bioactive Compounds and Antitumor Agents

There is an urgent need for new inhibitors against T. cruzi, a protozoal infection that affects about 8 million people annually around the world. In this study, we describe the synthesis, characterization, and the inhibitory effects of the chalcone (E)-1-(4-aminophenyl)-3-(benzo[b]thiophen-2-yl)prop‑2-en-1-one (BNZTHP) against T. cruzi Y strain forms. The molecular structure of this compound was characterized by spectroscopic techniques, and its potential against T. cruzi was evaluated by in vitro assays and in silico analysis. The structural data analyses allowed drawing the molecular structure of the BNZTHP chalcone. Computational quantum chemical calculations provided the normal modes of vibrations, the global chemical reactivity parameters, the most probable regions for electrophilic and nucleophilic reactive attacks, and the singlet states for BNZTHP chalcone. Regarding the activity against T. cruzi the compound exhibited more active on trypomastigote than epimastigote forms with lower toxic on LLC-MK2 host cells. Furthermore, it presented a more powerful inhibitory effect than benznidazole. From the molecular docking studies showed that trypomastigote forms were able to interact with the cruzain, trypanothione reductase, and TcGAPDH enzymes, indicating good affinity toward the active pocket. These results bring attention to the BNZTHP chalcone as candidate for the development of new option for the treatment of Chagas disease.