Semisynthetic ecdysteroid-cinnamic derivatives against Trypanosoma cruzi

Chagas disease is a serious tropical disease that affects millions of people. It is caused by Trypanosoma cruzi, a protozoan parasite. Common transmission occurs via stings of Triatominae bugs as vectors [1]. In this work, our aim was to prepare new bioactive ester derivatives of 20-hydroxyecdysone (20E), and test against T. Cruzi. 20E was reacted with cinnamic acid, EDCl and DMAP in mol. sieve. DCM for 4.5 days [2]. The crude products were purified via flash chromatography and RP-HPLC. Four ecdysteroid esters including 2 new compounds were obtained, and their structures were confirmed via NMR as the 2-, 2,3-, 2,22, and the 3,22-cinnamate of 20E. Together with the new 20E cinnamates, 52 previously prepared ecdysteroid derivatives were tested against Trypanosoma cruzi epimastigotes. 2,22- and 3,22 phenylpropanoid esters and 6-O-E and Z-tert-buthyl-oximether of 20-hydroxyecdysone diacetonide demonstrated promising, and parasite selective activity at 5 μM. Synthesis of the caffeate and ferulate derivatives of 20E are currently ongoing.

Publication History

Article published online:
13 December 2021

• References

• 1 Rassi A., Rassi A., Marin-Neto J.A. Chagas Disease. The Lancet 2010; 375 (9723): 1388-402
• 2 Xu S, Pei L, Li D. et al. Synthesis and antimycobacterial evaluation of natural oridonin and its enmein-type derivatives. Fitoterapia 2014; 99: 300-306