Journal
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
Volume 27, Issue 3, Pages 551-565Publisher
SOC BRASILEIRA QUIMICA
DOI: 10.5935/0103-5053.20150287
Keywords
kaurenoic acid; xylopic acid; click chemistry; antiplasmodial activity; PfATP6 inhibitors
Categories
Funding
- D FAPEMIG
- PDJ FAPEMIG
- PDJ CNPq
- D CNPq
- DTI2 CNPq
- DTI2 FAPEMIG
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We herein report the synthesis of hybrid kauranoid molecules of type 1,2,3-triazole-1,4-disubstituted aiming to improve the antimalarial activity of kaurenoic and xylopic acids. The Cu-I-catalyzed cycloaddition of azides and kauranoid terminal alkynes was explored as a hybridization strategy. Kauranoid terminal alkynes were prepared from kaurenoic and xylopic acids that were isolated from Wedelia paludosa D. C. (Asteraceae) and Xylopia frutescens Aubl. (Annonaceae). A total of 15 kauranoid derivatives, including nine new triazoles, were obtained and five out of these were more active than the original diterpenes. Interestingly, an increased activity was observed for a kauranoid propargyl ether. Interaction between ent-kaurane diterpene derivatives and Ca2+-ATPase (PfATP6) was investigated. Synthesis of diterpene derivatives emerges as a possible route to be explored in the quest of potentially new inhibitors of PfATP6.
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