Straightforward synthesis, characterization, and cytotoxicity evaluation of hybrids of natural alkaloid evodiamine/rutaecarpine and thieno[2, 3-d]pyrimidinones. Issue 1 (2nd January 2020)

• Record Type: Journal Article
• Authors: Nie, Li-Fei; Wang, Si-Si; Cao, Jian-Guo; Liu, Fei-Ze; Xiamuxi, Hainimu; Aisa, Haji Akber; Huang, Guo-Zheng
• Is Part Of: Journal of Asian natural products research. Volume 22:Issue 1(2020)
• Page Start: 69
• Page End: 82
• Publication Date: 2020-01-02
• Subjects: Thieno[2, 3-d]pyrimidinone -- evodiamine -- rutaecarpine -- hybrid -- cytotoxicity; Materia medica -- Asia -- Periodicals; Pharmacognosy -- Asia -- Periodicals; Medicinal plants -- Asia -- Periodicals; Medicine, Oriental -- Asia -- Periodicals; 615.321095
• DOI: 10.1080/10286020.2018.1540599
• Languages: English
• ISSNs: 1028-6020

Abstract

Abstract: Dozens of hybrids of natural alkaloid evodiamine/rutaecarpine and thieno[2, 3- d ]pyrimidinones were synthesized in a straightforward method by condensation of substituted 2 H -thieno[2, 3- d ][1, 3 ]oxazine-2, 4(1 H )-diones or N -methyl-2 H -thieno[2, 3- d ][1, 3 ]oxazine-2, 4(1 H )-dione with 3, 4-dihydro- β -carbolines. In vitro cytotoxic assay discovered that compounds 9a, 10e, 11a, 11d, 11f, and 12a could induce antiproliferation against four different types of human cancer cells while compounds 10f and 12e were inactive. Notably, compound 11a displayed potent cell cytotoxicity for human non-small cell lung cancer cells A549, PC-9, human prostate cancer cells PC-3, and human breast cancer cell line MCF-7. Furthermore, compound 11a exhibited strong colony formation inhibition to A549 cells. These results unfold potential anticancer therapeutic applications of hybrids of thieno[2, 3- d ]pyrimidinones and quinazolinones. Graphical Abstract: