72808-18-5

Basic information

• Product Name: 3-(HYDROXYIMINO)-URS-12-EN-28-OIC ACID
• Synonyms: 3-(HYDROXYIMINO)-URS-12-EN-28-OIC ACID
• CAS NO: 72808-18-5
• Molecular Formula: C30H47NO3
• Molecular Weight: 0
• Mol File: 72808-18-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(HYDROXYIMINO)-URS-12-EN-28-OIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(HYDROXYIMINO)-URS-12-EN-28-OIC ACID(72808-18-5)
• EPA Substance Registry System: 3-(HYDROXYIMINO)-URS-12-EN-28-OIC ACID(72808-18-5)

Safety Data

• Hazardous Substances Data: 72808-18-5(Hazardous Substances Data)

Upstream product

• 94482-51-6 ursonic acid 
• 77-52-1 ursolic acid 
• 5470-11-1 hydroxylamine hydrochloride 

Relevant articles and documents

Synthesis and antitumor activity evaluation of novel ursolic acid derivatives

Eleven novel ursolic acid (UA) derivatives were designed and synthesized with modification at positions of C-2, C-3, and C-28 of UA. Their structures were confirmed by MS, 1H NMR, and elemental analysis. Their in vitro cytotoxicities against various cancer cell lines (HeLa, HepG2, and BGC-823) were evaluated by MTT assay. The results indicated that all compounds could inhibit cell proliferation of HeLa, HepG2, and BGC-823 cells. Among them, compounds I3 and I4 showed more potent cytotoxicity on these three tumor cells than gefitinib (positive control), worthy to be studied further.

Synthesis and cytotoxic activity of ursolic acid derivatives

Fourteen ursolic acid derivatives, among them four novel compounds, were synthesized by modification either at the C-3, C-28 or both positions. The cytotoxic activity of the obtained derivatives was evaluated against the four human cancer cell lines KB (human mouth epidermal carcinoma), HepG2 (human hepatocellular carcinoma), MCF7 (human breast carcinoma) and Lu (human lung carcinoma). As the result, compounds 7 and 8 were from two to three times more active than ursolic acid on all four tested cell lines. This is the first report on cytotoxic effects of the synthetized ursolic acid derivatives 4, 8, and 10-15.

The cytotoxic activity of ursolic acid derivatives

Ursolic acid and 2α-hydroxyursolic acid isolated from apple peels were found to show growth inhibitory activity against four tumor cell lines, HL-60, BGC, Bel-7402 and Hela. Structural modifications were performed on the C-3, C-28 and C-11 positions of ursolic acid and the cytotoxicity of the derivatives was evaluated. The SAR revealed that the triterpenes possessing two hydrogen-bond forming groups (an H-donor and a carbonyl group) at positions 3 and 28 exhibit cytotoxic activity. The configuration at C-3 was found to be important for the activity. Introduction of an amino group increased the cytotoxicity greatly. A 3β-amino derivative was 20 times more potent than the parent ursolic acid. The 28-aminoalkyl dimer compounds showed selective cytotoxicity.