Synthesis and cytotoxicity of allobetulin derivatives

Abstract

The synthesis and screening of antitumor activity in vitro (cytotoxicity) of various oxygen, nitrogen, sulfur and platinum-containing derivatives of allobetulin, including different arrangements of the double bonds in the A and B rings, penta- and hexacyclic ring A, 21-acetyl-20,28-epoxy-18α,19βH-ursane-isomeric cycle E, was carry out. (3R,5R)-19β,28-Epoxy-4,5-seco-18α-olean-3(5)-ozonide and 2,3-indolo-21β-acetyl-20β,28-epoxy-18α, H-19β-ursane showed significant cytotoxic activity against melanoma MeWo and Leukemia SR cells, appropriately. (3S,5S)-Diastereomer of the first compound showed no cytotoxicity.

Inhibition of Alpha-Glucosidase by Synthetic Derivatives of Lupane, Oleanane, Ursane and Dammarane Triterpenoids

“…These studies indicate that triterpenoids are potential antiglycative agents and can be useful for treating glycation-related diseases such as diabetes mellitus [13]. The goal of the present work, as a part of our research into the chemistry and pharmacology of terpenoids [14][15][16][17][18][19][20][21][22], was to estimate the in vitro α-glucosidase inhibitory activity of oxygen and nitrogen containing triterpenoids, including those obtained earlier and new ones, the synthesis which is described below. Figure 1 show the synthesis of novel ursane (3) and dammarane (4) derivatives.…”

Simple structural modifications confer cytotoxicity to allobetulin

“…[23][24][25] Quite recently, a moderate activity was reported for an allobetulin derived ozonide. 26 The diminished cytotoxicity of allobetulin derivatives as compared to their parent betulin analog is not unexpected at all. The presence of a carbonyl or carboxyl group at C-28 of the betulin skeleton seems mandatory for obtaining good cytotoxicity, although there some exceptions to this rule of thumb.…”

Synthesis and the antineoplastic activity of imidazolides of betulonic acid

“…This work continues our studies on the synthesis and experimental examination of derivatives of plant terpenoids [18][19][20][21][22][23][24][25][26]. Considering that triterpene imi dazolides offer promise as potential antitumor agents, we describe here the synthesis and the results of the assessment of the antineoplastic activity of novel lupane imidazolides.…”