Design and synthesis of a phenyl C-glycoside derivative of Spliceostatin A and its biological evaluation toward prostate cancer treatment. Issue 51 (19th December 2019)

• Record Type: Journal Article
• Authors: Yoshikawa, Yusuke; Ishibashi, Airi; Murai, Kenichi; Kaneda, Yasufumi; Nimura, Keisuke; Arisawa, Mitsuhiro
• Is Part Of: Tetrahedron letters. Volume 60:Issue 51(2019)
• Publication Date: 2019-12-19
• Subjects: CRPC -- AR-V7 -- Spliceostatin A -- C-Glycoside; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151313
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Synthetic study of phenyl C- glycoside analogue of Spliceostatin A. An appropriate combination of Julia-coupling reaction as a key step. Phenyl C- glycoside analogue, as a moderate inhibitor for cancer cell growth and AR-V7 expression. Abstract: We designed and synthesized a novel phenyl C -glycoside analogue of Spliceostatin A, which is potent splicing inhibitor and has anti-cancer activities. We successfully synthesized its right phenyl C -glycoside sugar fragment in shorter steps compared to previous synthetic methods for Spliceostatin A and revealed an appropriate fragment combination with a Julia-coupling reaction. Regarding biological activity, the Ph- C -glycoside analogue of Spliceostatin A showed repressed cell proliferation in three prostate cancer cell lines and suppressed AR-V7 expression.