3-oxo-(17s)-17-(((dimethoxyphosphoryl)methoxy)carbonyl)-28-norolean-12(13)-ene

3-oxo-(17s)-17-(((dimethoxyphosphoryl)methoxy)carbonyl)-28-norolean-12(13)-ene is a semisynthetic pentacyclic triterpenoid derivative featuring a methylphosphonate moiety at the C17 position. It is derived from oleanonic acid (3-oxo-oleanolic acid), a natural phytochemical known for its anticancer potential. This specific derivative was synthesized to overcome the poor bioavailability and pharmacokinetic limitations of natural triterpenic acids. Experimental evaluations against the B164A5 murine melanoma cell line have demonstrated that the compound possesses enhanced antiproliferative and anti-migratory properties compared to its parent compound. Its mechanism of action involves the induction of apoptosis, as evidenced by nuclear condensation and dose-dependent declines in cell viability. Preliminary safety evaluations using the HET-CAM assay indicate a lack of acute vascular toxicity, suggesting its potential for further development as an antimelanoma strategy.

Other names

3-oxo-oleanolic acid dimethoxyphosphorylmethyl esteroleanonic acid dimethoxyphosphorylmethyl esterdimethoxyphosphorylmethyl 3-oxo-olean-12-en-28-oatedimethoxyphosphorylmethyl3-oxo-olean-12-en-28-oatedimethoxyphosphorylmethyl-3-oxo-olean-12-en-28-oate