Synthesis, biological evaluation and mechanism of action of benzothiazole derivatives with aromatic hydrazone moiety, a new class of antileishmanial compounds

Author:

Coimbra Elaine Soares1ORCID,Antinarelli Luciana M. R.1,de Oliveira Lemos Ari Sérgio1,da Silva Neto Adolfo Firmino2,Pinheiro Alessandra Campbell3,de Souza Marcus Vinícius Nora3

Affiliation:

1. Departamento de Parasitologia, Microbiologia e Imunologia Instituto de Ciências Biológicas, Universidade Federal de Juiz de Fora Juiz de Fora Brazil

2. Departamento de Medicina Veterinária, Faculdade de Medicina Universidade Federal de Juiz de Fora Juiz de Fora Minas Gerais Brazil

3. Fundação Oswaldo Cruz Instituto de Tecnologia em Fármacos‐Far Manguinhos Rio de Janeiro Rio de Janeiro Brazil

Abstract

AbstractLeishmaniasis is a disease caused by protozoa Leishmania spp., considered as a significant and urgent public health problem mainly in developing countries. In the absence of an effective vaccine, the treatment of infected people is one of the most commonly prophylactic measures used to control this disease. However, the therapeutic arsenal is reduced to a few drugs, with serious side effects and variability in efficacy. Attempting to this problem, in this work, a series of benzothiazole derivatives was synthetized and assayed against promastigotes and intracellular amastigotes of L. amazonensis, as well as the toxicity on macrophages. In addition, studies about the mechanism of action were also performed. Among the synthesized molecules, the substitution at position 4 of the aromatic ring appears to be critical for activity. The best compound exhibited IC50 values of 28.86 and 7.70 μM, against promastigotes and amastigotes of L. amazonensis, respectively, being more active than miltefosine, used as reference drug. The in silico analysis of physicochemical and pharmacokinetic (ADMET) properties of this compound suggested a good profile of oral bioavailability and safety. In conclusion, the strategy of using benzothiazole nucleous in the search for new antileishmanial agents was advantageous and preliminar data provide information about the mechanism of action as well as in silico parameters suggest a good profile for preclinical studies.

Publisher

Wiley

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