Synthesis and anticancer evaluation of novel 9α-substituted-13-(1, 2, 3-triazolo)-parthenolides. Issue 24 (15th June 2016)

• Record Type: Journal Article
• Authors: Zaki, Mohamed; Allouchi, Hassan; El Bouakher, Abderrahman; Duverger, Eric; El Hakmaoui, Ahmed; Daniellou, Richard; Guillaumet, Gérald; Akssira, Mohamed
• Is Part Of: Tetrahedron letters. Volume 57:Issue 24(2016)
• Page Start: 2591
• Page End: 2594
• Publication Date: 2016-06-15
• Subjects: 9α-Hydroxyparthenolide -- 1, 3-Dipolar cycloaddition reaction -- 9α-Trimethylsiloxy-13-(1, 2, 3-triazolo)-parthenolide -- 9α-Hydroxy-13-(1, 2, 3-triazolo)-parthenolide -- Anticancer activity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.04.115
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: 9α-Hydroxyparthenolide was obtained from the plant Anvillea radiata . Regio- and stereoselective synthesis of new C9- and C13-substituted parthenolides. 9α-Hydroxyparthenolide derivatives were tested for their in vitro anticancer activity. Abstract: A series of novel 9α-substituted-13-(1, 2, 3-triazolo)-parthenolides3 –20 were efficiently synthesized and tested for their in vitro anticancer activity using the MTT colorimetric assay against four human cancer cell lines. 9α-Substituted-13-(1, 2, 3-triazolo)-parthenolide derivatives were prepared by the diastereoselective Michael addition of TMSN3 onto 9α-hydroxyparthenolide1 to give the key intermediate 9α-trimethylsilyloxy-13-(1, 2, 3-triazolo)-parthenolide2 which was utilized in a regioselective Huisgen 1, 3-dipolar cycloaddition reaction with various alkynes to afford 1, 4-disubstituted-1, 2, 3-triazoles of 9α-substituted-parthenolide.