Natural chromenes and chromene derivatives as potential anti-trypanosomal agents.

Abstract

The aim of the study was to investigate the anti-trypanocidal activities of natural chromene and chromene derivatives. Five chromenes were isolated from Piper gaudichaudianum and P. aduncum, and a further seven derivatives were prepared using standard reduction, methylation and acetylation procedures. These compounds were assayed in vitro against epimastigote forms of Trypanosoma cruzi, the causative agent of Chagas disease. The results showed that the most of the compounds, especially those possessing electron-donating groups as substituents on the aromatic ring, showed potent trypanocidal activity. The most active compound, [(2S)-methyl-2-methyl-8-(3''-methylbut-2''-enyl)-2-(4'-methylpent-3'-enyl)-2H-chromene-6-carboxylate], was almost four times more potent than benznidazole (the positive control) and showed an IC50 of 2.82 microM. The results reveal that chromenes exhibit significant anti-trypanocidal activities and indicate that this class of natural product should be considered further in the development of new and more potent drugs for use in the treatment of Chagas disease.

• Authors: João Marcos Batista Jr, Adriana Aparecida Lopes, Daniela Luz Ambrósio, Luis Octávio Regasini, Massuo Jorge Kato, Vanderlan da Silva Bolzani, Regina Maria Barretto Cicarelli, Maysa Furlan
• Journal: Biological & pharmaceutical bulletin (Biol Pharm Bull) Vol. 31 Issue 3 Pg. 538-40 (Mar 2008) ISSN: 0918-6158 [Print] Japan
• PMID: 18310927 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Benzopyrans
• Trypanocidal Agents

Topics

• Animals
• Benzopyrans (chemical synthesis, isolation & purification, pharmacology)
• Parasitic Sensitivity Tests
• Piper (chemistry)
• Structure-Activity Relationship
• Trypanocidal Agents (chemical synthesis, isolation & purification, pharmacology)
• Trypanosoma cruzi (drug effects)