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Synthetic Aspects and First-time Assessment of 2-amino-1,3-selenazoles Against Mycobacterium tuberculosis

[ Vol. 15 , Issue. 11 ]

Author(s):

Victor Facchinetti, Marcus V.N. De Souza*, Ana C.S. Nery, Stephane L. Calixto, Juliana T. Granato, Elaine S. Coimbra, Maria C.S. Lourenco, Claudia R.B. Gomes and Thatyana R.A. Vasconcelos   Pages 1224 - 1229 ( 6 )

Abstract:


Background: 2-aminoselenazoles became an important core in medicinal chemistry after the discovery of Ebselen and Ethaselen. Therefore, many researchers have reported the synthesis of small selenazole intermediates via Hantzsch cyclization using a wide array of methodologies and catalysts.

Methods: In this work, we investigated the formation of 2-aminoselenazoles on various organic solvents and in water, under catalyst-free conditions. Moreover, these molecules and their 2-aminothiazoles analogues were assessed in vitro for their antitubercular activity against Mycobacterium tuberculosis and the results compared.

Results: Instant reactions were observed when using polar aprotic solvents and all selenazoles were synthesized in water using sonochemistry. Furthermore, two selenazoles and one thiazole displayed activity in the µM range and the selenium heterocycles seems to be more potent than their sulphur analogues.

Conclusion: This is the first study of selenazoles against M. tuberculosis. It is noteworthy that 2-amino-1,3-selenazoles are interesting synthetic intermediates that could be incorporated into novel prototypes against tuberculosis.

Keywords:

Tuberculosis, selenazole, synthesis, methodology, ultrasound, hantzsch cyclization.

Affiliation:

Departamento de Quimica Organica, Programa de Pos-Graduacao em Quimica, Instituto de Quimica, Universidade Federal Fluminense, Outeiro de Sao Joao Batista, s/no, Centro, Niteroi, 24020-141, Rio de Janeiro, Fundacao Oswaldo Cruz, Instituto de Tecnologia em Farmacos-Farmanguinhos, Rua Sizenando Nabuco 100, Manguinhos, 21041- 250, Rio de Janeiro, RJ, Fundacao Oswaldo Cruz, Instituto de Tecnologia em Farmacos-Farmanguinhos, Rua Sizenando Nabuco 100, Manguinhos, 21041- 250, Rio de Janeiro, RJ, Departamento de Parasitologia Microbiologia e Imunologia, Instituto de Ciencias Biologicas, Universidade Federal de Juiz de Fora, Rua Jose Lourenco Kelmer, s/n- Campus Universitario, Bairro Sao Pedro, 36036-900-Juiz de Fora, MG, Departamento de Parasitologia Microbiologia e Imunologia, Instituto de Ciencias Biologicas, Universidade Federal de Juiz de Fora, Rua Jose Lourenco Kelmer, s/n- Campus Universitario, Bairro Sao Pedro, 36036-900-Juiz de Fora, MG, Departamento de Parasitologia Microbiologia e Imunologia, Instituto de Ciencias Biologicas, Universidade Federal de Juiz de Fora, Rua Jose Lourenco Kelmer, s/n- Campus Universitario, Bairro Sao Pedro, 36036-900-Juiz de Fora, MG, Fundacao Oswaldo Cruz, Instituto Nacional de Infectologia-INI, Servico de Bacteriologia. Av. Brazil, 4365, Manguinhos, 21045-900-Rio de Janeiro, RJ, Fundacao Oswaldo Cruz, Instituto de Tecnologia em Farmacos-Farmanguinhos, Rua Sizenando Nabuco 100, Manguinhos, 21041- 250, Rio de Janeiro, RJ, Departamento de Quimica Organica, Programa de Pos-Graduacao em Quimica, Instituto de Quimica, Universidade Federal Fluminense, Outeiro de Sao Joao Batista, s/no, Centro, Niteroi, 24020-141, Rio de Janeiro

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