Regioselective Transformation of the Cyano Group of Triterpene α,β-Alkenenitriles

• Published in: Chemistry of natural compounds Vol. 53; no. 4; pp. 687 - 690
• Main Authors: Konysheva, A. V., Tolmacheva, I. A., Savinova, O. V., Boreko, E. I., Grishko, V. V.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-07-2017; Springer Nature B.V
• Subjects: Accessibility; Alkenes; Fragments; Hydrolysis; Medicine; Organic Chemistry; Pharmacy; Plant Sciences; Regioselectivity; Synthesis; Viruses; ceanothane-type triterpenoids; herpes simplex virus type 1; alkenenitriles; virucidal activity; betulin; DIBAL-H; hydrolysis
• ISSN: 0009-3130; 1573-8388
• DOI: 10.1007/s10600-017-2091-3

Unsaturated acids, including difficultly accessible ceanothane-type ones, were prepared via alkaline hydrolysis of semi-synthetic triterpenoids with 1-cyano- or 3-methyl-1-cyanoalkene fragments in five-membered ring A. Regioselective reduction of 1-cyano-19
β
,28-epoxy-2-nor-18
αH
-olean-1(3)-ene by DIBAL-H synthesized 2-aminomethyl-19
β
,28-epoxy-2-nor-18
αH
-olean-1(3)-ene. The synthesized triterpene derivatives possessed virucidal activity against herpes simplex virus type 1 (HSV-1) according to screening for inhibitory and virucidal activity. Methyl ceanotha-1(3),20(30)-dien-2,28-dioic acid
5
(ET
50
28.3 min) and its 3-methyl derivative
7
(ET
50
17.7 min) were the most active compounds.