Betulinic acid, oleanolic acid and ursolic acid have been modified at the C-3 position to cinnamate-based esters and in vitro antimycobacterial activity against Mycobacterium tuberculosis H 37 Ra has been determined. The results indicated that modification of the parent structures of betulinic acid, oleanolic acid and ursolic acid to the p-coumarate and, in the case of the latter two triterpenes, the ferulate ester analogues resulted in high antimycobacterial activity. Structure-activity relationships within the lupane, oleanane and ursane analogues and between these triterpenes are discussed.
Terpenes U 0200Antimycobacterial Activity of Cinnamate-Based Esters of the Triterpenes Betulinic, Oleanolic and Ursolic Acids. -The title compounds are modified at the C-3 position by esterification with cinnamic acid derivatives and the antimycobacterial activity of these products against Mycobacterium tuberculosis H37Ra is studied. The betulinic acid derivative (I), the oleanolic acid derivative (II), and the ursolic acid derivatives (III) show the best results. -(TANACHATCHAIRATANA, T.; BREMNER, J. B.; CHOKCHAISIRI, R.; SUKSAMRARN*, A.; Chem.
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