Synthesis and immunotropic activity of methyl esters of 2-alkylaminomethylene-3-oxolup-20(29)-en-28-ic acids

Abstract

New lupane beta-enaminoketones were synthesized by interaction of methyl 2-hydroxymethylene-3-oxolup-20(29)-en-28-oate with aliphatic amines. Immunotropic activity was found for some of these compounds.

Synthesis of C2 symmetric triterpene bis-enaminones

“…In particular, C-2 condensation reactions of triterpene 2-hydroxymethylene derivatives to form open and cyclic heteroatomic compounds that exhibit various biological activities were described [6][7][8]. We prepared previously N-containing triterpenoids with pronounced immunotropic activity [9][10][11] that were promising for modification by a stable C-2 enaminone [12,13] via the reaction of lupane-and oleanane-type 2-hydroxymethylen-3-ones (1 and 5) with monoamines. An attempt to prepare symmetric condensation products of the triterpene 2-hydroxymethylene derivatives (1 and 5) with diamines under the published conditions [9] did not give the expected result.…”