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. 2013 May 29;18(6):6366-82.
doi: 10.3390/molecules18066366.

Design, synthesis and trypanocidal evaluation of novel 1,2,4-triazoles-3-thiones derived from natural piperine

Tatiany Nunes Franklim  1 , Leonardo Freire-de-Lima, Julliana de Nazareth Sá Diniz, José Osvaldo Previato, Rosane Nora Castro, Lucia Mendonça-Previato, Marco Edilson Freire de Lima
Affiliations

Design, synthesis and trypanocidal evaluation of novel 1,2,4-triazoles-3-thiones derived from natural piperine

Tatiany Nunes Franklim et al. Molecules. .

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.

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Figures

Figure 1
Figure 1
Chemical structures of piperine (1), nifurtimox (2) and benznidazole (3).
Figure 2
Figure 2
Strategies on the designing of new piperine-triazole hybrid.
Scheme 1
Scheme 1
Preparation of new 1,2,4-triazole-2-thiones 9a–9m from piperine (1).
See this image and copyright information in PMC

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