Synthesis of new N,S-acetal analogs derived from juglone with cytotoxic activity against Trypanossoma cruzi

J Bioenerg Biomembr. 2020 Jun;52(3):199-213. doi: 10.1007/s10863-020-09834-8. Epub 2020 May 17.

Abstract

A series of 11 new N,S-acetal juglone derivatives were synthesized and evaluated against T. cruzi epimastigote forms. These compounds were obtained in good to moderate yields using a microwave irradiation protocol. Among all compounds, two N,S-acetal analogs, showed significant trypanocidal activity. Notably, one compound 11g exhibited selectivity index 10-fold higher than the reference drug benznidazole for epimastigote. The compound 11h was more effective for amastigote forms. Both prototypes exhibited S.I. higher than the benznidazole description. Thus, both compounds proving to be useful candidate molecules to further studies in infected animals.

Keywords: N,S-acetal; Naphtoquinones; Trypanosoma cruzi.

MeSH terms

  • Acetals / metabolism*
  • Chagas Disease / drug therapy*
  • Trypanosoma cruzi / drug effects*

Substances

  • Acetals