Synthesis and evaluation of novel prenylated chalcone derivatives as anti-leishmanial and anti-trypanosomal compounds

Thais Gaban Passalacqua; Luiz Antonio Dutra; Letícia de Almeida; Angela Maria Arenas Velásquez; Fabio Aurelio Esteves Torres; Paulo Renato Yamasaki; Mariana Bastos dos Santos; Luis Octavio Regasini; Paul A M Michels; Vanderlan da Silva Bolzani; Marcia A S Graminha

doi:10.1016/j.bmcl.2015.05.072

Synthesis and evaluation of novel prenylated chalcone derivatives as anti-leishmanial and anti-trypanosomal compounds

Bioorg Med Chem Lett. 2015 Aug 15;25(16):3342-5. doi: 10.1016/j.bmcl.2015.05.072. Epub 2015 May 30.

Affiliations

¹ Instituto de Química, UNESP, Araraquara, SP 14800-060, Brazil; Programa de Pós Graduação em Biotecnologia, Brazil.
² Faculdade de Ciências Farmacêuticas, Universidade Estadual Paulista, UNESP, Araraquara, SP 14801-902, Brazil; Programa de Pós Graduação em Ciências Farmacêuticas, Brazil.
³ Faculdade de Ciências Farmacêuticas, Universidade Estadual Paulista, UNESP, Araraquara, SP 14801-902, Brazil.
⁴ Instituto de Biociências, Letras e Ciências Exatas, Universidade Estadual Paulista, UNESP, São José do Rio Preto, SP 15054-000, Brazil.
⁵ Institute of Structural and Molecular Biology, University of Edinburgh, UK.
⁶ Instituto de Química, UNESP, Araraquara, SP 14800-060, Brazil.
⁷ Programa de Pós Graduação em Biotecnologia, Brazil; Faculdade de Ciências Farmacêuticas, Universidade Estadual Paulista, UNESP, Araraquara, SP 14801-902, Brazil. Electronic address: [email protected].

PMID: 26055530
DOI: 10.1016/j.bmcl.2015.05.072

Abstract

Chalcones form a class of compounds that belong to the flavonoid family and are widely distributed in plants. Their simple structure and the ease of preparation make chalcones attractive scaffolds for the synthesis of a large number of derivatives enabling the evaluation of the effects of different functional groups on biological activities. In this Letter, we report the successful synthesis of a series of novel prenylated chalcones via Claisen-Schmidt condensation and the evaluation of their effect on the viability of the Trypanosomatidae parasites Leishmania amazonensis, Leishmania infantum and Trypanosoma cruzi.

Keywords: Drug discovery; Leishmania amazonensis; Leishmania infantum; Leishmanicidal activity; Prenylated chalcone; Trypanocidal activity; Trypanosoma cruzi.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chalcone / chemical synthesis*
Chalcone / chemistry
Chalcone / pharmacology*
Inhibitory Concentration 50
Leishmania infantum / drug effects*
Prenylation
Structure-Activity Relationship
Trypanocidal Agents / chemical synthesis
Trypanocidal Agents / chemistry
Trypanocidal Agents / pharmacology
Trypanosoma cruzi / drug effects*

Substances

Trypanocidal Agents
Chalcone