108650-45-9

Basic information

• Product Name: 3β-benzoyloxy-urs-12-en-28-oic acid
• Synonyms: 3β-benzoyloxy-urs-12-en-28-oic acid
• CAS NO: 108650-45-9
• Molecular Weight: 560.817
• Mol File: 108650-45-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3β-benzoyloxy-urs-12-en-28-oic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3β-benzoyloxy-urs-12-en-28-oic acid(108650-45-9)
• EPA Substance Registry System: 3β-benzoyloxy-urs-12-en-28-oic acid(108650-45-9)

Safety Data

• Hazardous Substances Data: 108650-45-9(Hazardous Substances Data)

Upstream product

• 77-52-1 ursolic acid 
• 93-97-0 benzoic acid anhydride 
• 65-85-0 benzoic acid 
• 192211-41-9 benzyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,-11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate 

Relevant articles and documents

Synthesis, biological evaluation and SAR studies of ursolic acid 3β-ester derivatives as novel CETP inhibitors

Cholesteryl ester transfer protein (CETP) is an attractive therapeutic target for the prevention and treatment of cardiovascular diseases by lowering low-density lipoprotein cholesterol levels as well as raising high-density lipoprotein cholesterol levels in human plasma. Herein, a series of ursolic acid 3β-ester derivatives were designed, synthesized and evaluated for the CETP inhibiting activities. Among these compounds, the most active compound is U12 with an IC50 value of 2.4 μM in enzymatic assay. The docking studies showed that the possible hydrogen bond interactions between the carboxyl groups at both ends of the molecule skeleton and several polar residues (such as Ser191, Cys13 and Ser230) in the active site region of CETP could significantly enhance the inhibition activity. This study provides structural insight of the interactions between these pentacyclic triterpenoid 3β-ester derivatives and CETP protein for the further modification and optimization.

Synthesis and evaluation of the HIF-1α inhibitory activities of novel ursolic acid tetrazole derivatives

The hypoxia-inducible factor-1α (HIF-1α) pathway has been implicated in tumor angiogenesis, growth, and metastasis. Therefore, the inhibition of this pathway is an important therapeutic target for the treatment of various types of cancers. Here, we designed and synthesized 31 ursolic acid (UA) derivatives containing a tetrazole moiety and evaluated them for their potential anti-tumor activities as HIF-1α transcriptional inhibitors. Of these, compound 14d (IC50 0.8 ± 0.2 μM) displayed the most potent activity and compounds 14a (IC50 4.7 ± 0.2 μM) exhibited the most promising biological profile. Analysis of the structure–activity relationships of these compounds with HIF-1α suggested that the presence of a tetrazole group located at C-28 of the UA derivatives was critical for their inhibitory activities.