Title:Synthetic Aspects and First-time Assessment of 2-amino-1,3-selenazoles Against Mycobacterium tuberculosis
Volume: 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
Affiliation:
- Fundacao Oswaldo Cruz, Instituto de Tecnologia em Farmacos-Farmanguinhos, Rua Sizenando Nabuco 100, Manguinhos, 21041- 250, Rio de Janeiro, RJ,Brazil
Keywords:
Tuberculosis, selenazole, synthesis, methodology, ultrasound, hantzsch cyclization.
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.
