A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: design, synthesis, and biological evaluation

• Published in: Organic & biomolecular chemistry Vol. 13; no. 5; pp. 1507 - 1514
• Main Authors: Wei, Gaofei, Luan, Weijing, Wang, Shuai, Cui, Shanshan, Li, Fengran, Liu, Yongxiang, Liu, Yang, Cheng, Maosheng
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 07.02.2015
• Subjects: Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Apoptosis - drug effects; Cell Line, Tumor; Chemistry; Chemistry Techniques, Synthetic; Chemistry, Organic; Drug Design; Humans; Inhibitory Concentration 50; Membrane Potential, Mitochondrial - drug effects; Oleanolic Acid - analogs & derivatives; Oleanolic Acid - chemical synthesis; Oleanolic Acid - chemistry; Oleanolic Acid - pharmacology; Physical Sciences; Science & Technology; Structure-Activity Relationship; Triazoles - chemistry; BREAST-CANCER CELLS; APOPTOSIS; NITRIC-OXIDE PRODUCTION; ACTIVATED RECEPTOR-GAMMA; CDDO-ME; TRITERPENOIDS; GROWTH ARREST; MOUSE MACROPHAGES; UP-REGULATION; 2-CYANO-3,12-DIOXOOLEAN-1,9-DIEN-28-OIC ACID
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c4ob01605j

A series of novel oleanolic acid coupled 1,2,3-triazole derivatives have been designed and synthesized by employing a Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The anti-proliferative evaluation indicated that some compounds exhibited excellent anti-cancer activity against the examined cancer cell lines. Among all derivatives, compound 3t possesses the best inhibitory activity against HT1080 cells. A series of pharmacology experiments show that compound 3t significantly induced HT1080 cell apoptosis. Therefore, this compound can serve as a promising lead candidate for further study.