1520096-22-3Relevant academic research and scientific papers
Discovery, optimization, and pharmacophore modeling of oleanolic acid and analogues as breast cancer cell migration and invasion inhibitors through targeting Brk/Paxillin/Rac1 axis
Elsayed, Heba E.,Akl, Mohamed R.,Ebrahim, Hassan Y.,Sallam, Asmaa A.,Haggag, Eman G.,Kamal, Amel M.,El Sayed, Khalid A.
, p. 231 - 243 (2015)
Bioassay-guided fractionation of Terminalia bentzoe L. leaves methanol extract identified the known triterpene oleanolic acid (1) as its major breast cancer cell migration inhibitor. Further chemical optimization afforded five new (9-12 and 15) and seven
Rational design and synthesis of topoisomerase i and II inhibitors based on oleanolic acid moiety for new anti-cancer drugs
Ashour, Ahmed,El-Sharkawy, Saleh,Amer, Mohamed,Abdel Bar, Fatma,Katakura, Yoshinori,Miyamoto, Tomofumi,Toyota, Nozomi,Bang, Tran Hai,Kondo, Ryuichiro,Shimizu, Kuniyoshi
, p. 211 - 220 (2014/01/17)
Semisynthetic reactions were conducted on oleanolic acid, a common plant-derived oleanane-type triterpene. Ten rationally designed derivatives of oleanolic acid were synthesized based on docking studies and tested for their topoisomerase I and IIα inhibitory activity. Semisynthetic reactions targeted C-3, C-12, C-13, and C-17. Nine of the synthesized compounds were identified as new compounds. The structures of these compounds were confirmed by spectroscopic methods (1D, 2D NMR and MS). Five oleanolic acid analogues (S2, S3, S5, S7 and S9) showed higher activity than camptothecin (CPT) in the topoisomerase I DNA relaxation assay. Four oleanolic acid analogues (S2, S3, S5 and S6) showed higher activity than etoposide in a topoisomerase II assay. The results indicated that the C12-C13 double bond of the oleanolic acid skeleton is important for the inhibitory activity against both types of topoisomerases, while insertion of a longer chain at either position 3 or 17 increases the activity against topoisomerases by various degrees. Some of the synthesized compounds act as dual inhibitors for both topoisomerase I and IIα.
