Partial synthesis of 14-deoxy-14-aminotriptolide. Issue 17 (27th April 2016)

• Record Type: Journal Article
• Authors: Kaloun, El Bachir; Long, Christophe; Molinier, Nicolas; Brel, Viviane; Cantagrel, Frédéric; Massiot, Georges
• Is Part Of: Tetrahedron letters. Volume 57:Issue 17(2016)
• Page Start: 1895
• Page End: 1898
• Publication Date: 2016-04-27
• Subjects: Triptolide -- Reductive amination -- Aminotriptolide -- Cytotoxicity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.03.060
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Nucleophilic attack on triptolide mesylate yields epoxide opening and rearrangement. Borch reduction of triptonide yields aminotriptolide. Replacement of OH in triptolide by a primary amine strongly decreases cytotoxicity. Abstract: Triptolide is a diterpene triepoxide isolated from Tripterygium wilfordii, a Chinese medicinal plant and possessing a wealth of biological activities. In order to produce more soluble derivatives of triptolide, its 14-amino analogue was prepared. Initial attempts at its preparation using classical displacements led to rearranged compounds and success was finally met using carefully controlled Borch conditions. 14-Deoxy-14-aminotriptolide was thus prepared for the first time and it was found 10 times less cytotoxic than the parent compound.