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Design, Synthesis and Trypanocidal Evaluation of Novel 1,2,4-Triazoles-3-thiones Derived from Natural Piperine
Departamento de Química, Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, BR 465, Km 07, CEP: 23.890-000, Seropédica, RJ, Brazil
Cidade Universitária, Ilha do Fundão, Instituto de Biofísica Carlos Chagas Filho, Universidade Federal do Rio de Janeiro, CEP: 21.941-902, Rio de Janeiro, RJ, Brazil
* Author to whom correspondence should be addressed.
Received: 29 March 2013; in revised form: 16 May 2013 / Accepted: 21 May 2013 / Published: 29 May 2013
Abstract: The work reported herein describes the synthesis and the assessment of the trypanocidal activity of thirteen new 1,2,4-triazole-3-thiones obtained from natural piperine, the main constituent of the dry fruits of Piper nigrum. It is part of a research program aiming to use abundant and easily available natural products as starting materials for the design and synthesis of new molecules potentially useful as antiparasitic drugs. The variously substituted triazole derivatives were synthesized from the natural amide in four steps with the use of microwave irradiation on overall yields ranging from 32% to 51%. The cyclohexyl substituted derivative showed the best trypanocidal profile on proliferative forms of Trypanosoma cruzi (Y strain), with IC50s = 18.3 and 8.87 mM against epimastigotes and amastigotes, respectively.
Keywords: Trypanosoma cruzi; Piper nigrum; antiparasitic drugs; bioisosterism; molecular hybridization
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Franklim, T.N.; Freire-de-Lima, L.; de Nazareth Sá Diniz, J.; Previato, J.O.; Castro, R.N.; Mendonça-Previato, L.; de Lima, M.E.F. Design, Synthesis and Trypanocidal Evaluation of Novel 1,2,4-Triazoles-3-thiones Derived from Natural Piperine. Molecules 2013, 18, 6366-6382.
Franklim TN, Freire-de-Lima L, de Nazareth Sá Diniz J, Previato JO, Castro RN, Mendonça-Previato L, de Lima MEF. Design, Synthesis and Trypanocidal Evaluation of Novel 1,2,4-Triazoles-3-thiones Derived from Natural Piperine. Molecules. 2013; 18(6):6366-6382.
Franklim, Tatiany N.; Freire-de-Lima, Leonardo; de Nazareth Sá Diniz, Julliana; Previato, José O.; Castro, Rosane N.; Mendonça-Previato, Lucia; de Lima, Marco E.F. 2013. "Design, Synthesis and Trypanocidal Evaluation of Novel 1,2,4-Triazoles-3-thiones Derived from Natural Piperine." Molecules 18, no. 6: 6366-6382.