915-79-7

Upstream product

• 77-52-1 ursolic acid 
• 108-24-7 acetic anhydride 
• 86996-88-5 3β-acetoxyurs-12-en-28-al 
• 64-19-7 acetic acid 
• 77-52-1 ursolic acid 
• 64-17-5 ethanol 
• 884310-54-7 acetic acid-(3β-acetoxy-ursen-(12)-oic acid-(28))-anhydride 
• 77-52-1 Ursolic acid 
• 75-36-5 acetyl chloride 
• 160911-62-6 3β-(acetyloxy)-11α,12α-epoxy-14α-hydroxyurs-28-oic acid δ-lactone 

Downstream Products

• 990-89-6 methyl 3-acetylursolate 
• 545-46-0 uvaol 
• 71623-71-7 11-oxo-ursolic acid acetate 
• 35959-08-1 3β-acetoxyurs-11-en-28,13-olide 
• 104668-95-3 phenyl-3β-acetoxy-urs-12-en-28-oate 
• 1437303-18-8 3β-phthaloyl-urs-12-en-28-carboxamide 
• 94482-51-6 ursonic acid 
• 1613030-98-0 N-(3-β-acetoxy-ursane-12-ene-28-acyl)-o-fluoroaniline 
• 1613030-99-1 N-(3-β-acetoxy-ursane-12-ene-28-acyl)-o-chloroaniline 
• 1613031-00-7 N-(3-β-acetoxy-ursane-12-ene-28-acyl)-o-bromoaniline 
• 929076-64-2 N-(3-β-acetoxy-ursane-12-ene-28-acyl)-aniline 

Relevant academic research and scientific papers

N-methylated diazabicyclo[3.2.2]nonane substituted triterpenoic acids are excellent, hyperbolic and selective inhibitors for butyrylcholinesterase

Triterpenoic acids (oleanolic, ursolic, betulinic, platanic and glycyrrhetinic acid) were acetylated and coupled with 1,3- or 1,4-diazabicyclo[3.2.2]nonanes to yield amides. Reaction of these amides with methyl iodide at the distal nitrogen of the bicyclic system gave the corresponding quaternary ammonium salts. These compounds were shown to act as excellent inhibitors of the enzyme butyrylcholinesterase (BChE) while being only weak inhibitors for acetylcholinesterase (AChE). Evaluation of the enzyme kinetics revealed these compounds to act as hyperbolic inhibitors for BChE while the results from molecular modeling gave an explanation for their selectivity between AChE and BChE.

Discovery and radiosensitization research of ursolic acid derivatives as SENP1 inhibitors

SUMOylation and deSUMOylation plays an important role in DNA damage response and the formation of radiotherapy resistance. SENP1 is the main specific isopeptidase to catalyze deSUMOylation modification. Inhibiting SENP1 upregulates cancer cell radiosensitivity and it becomes a promising target for radiosensitization. Herein, based on the structure of ursolic acid (UA), a total of 53 pentacyclic triterpene derivatives were designed and synthesized as SENP1 inhibitors. Ten derivatives exhibited better SENP1 inhibitory activities than UA and the preliminary structure-activity relationship was discussed. Most of the UA derivatives were low-cytotoxic, among which compound 36 showed the best radiosensitizing activity with the SER value of 1.45. It was the first study to develop small molecular SENP1 inhibitors as radiosensitizers.

Pentacyclic triterpenoid TGR5 receptor stimulant, preparation method and application thereof

The invention discloses a pentacyclic triterpenoid TGR5 receptor stimulant, a preparation method and application of the pentacyclic triterpenoid TGR5 receptor stimulant. The structure of the pentacyclic triterpenoid TGR5 receptor stimulant is as shown in a formula I, and the definition of each substituent is as shown in the specification and claims. According to the pentacyclic triterpenoid compound, the solubility is increased, the permeability is improved, the TGR5 receptor agonist activity is remarkably improved, Caco-2 monolayer cells can be penetrated, and the in-vivo drug effect exertion of the compound after oral administration is guaranteed. The TGR5 receptor stimulant is expected to be further developed into a medicine for treating metabolic diseases represented by diabetes.

MSBA-S – A pentacyclic sulfamate as a new option for radiotherapy of human breast cancer cells

Many pentacyclic triterpenoids show anti-cancer and anti-inflammatory properties. Recently, we detected a pronounced cytotoxicity and radiosensitivity of two betulinyl sulfamates in human breast cancer cells. Besides betulinic acid scaffold (BSBA-S), we synthesized several new sulfamate-coupled scaffolds from oleanolic acid (OSBA-S), ursolic acid (USBA-S), platanic acid (PSBA-S) and maslinic acid (MSBA-S). Highest cytotoxicity was monitored in breast cancer cell lines after MSBA-S treatment showing in SRB assays IC50 values between 3.7 μM and 5.8 μM. Other sulfamate/triterpene conjugates, however, were less cytotoxic holding IC50 values between 6.6 μM and >50 μM, respectively. MSBA-S-treated breast cancer cells displayed significantly reduced clonogenic survival and an increased rate of apoptosis as compared to the other conjugates. In addition, MSBA-S in combination with irradiation resulted in effects on radiosensitivity in MDA-MB-231 cells (DMF10 = 1.14). In particular, ROS formation was strongly assessed in MSBA-S-treated breast cancer cells. Our findings suggest that the sulfamate derivative of maslinic acid MSBA-S might be a new option for the radiation therapy in breast cancer cells.

Cytotoxic triterpenoid–safirinium conjugates target the endoplasmic reticulum

Safirinium P and Q fluorescence labels were synthesized and conjugated with spacered triterpenoic acids to access hybrid structures. While the parent safirinium compounds were not cytotoxic at all, many triterpenoid safirinium P and Q conjugates showed moderate cytotoxicity. An exception, however, was safirinium P derived compound 30 holding low EC50 = 5.4 μM (for A375 cells) to EC50 = 7.5 μM (for FaDu cells) as well as EC50 = 6.6 μM for non-malignant fibroblasts NIH 3T3. Fluorescence imaging showed that the safirinium core structures cannot enter the cells (not even after a prolonged incubation time of 24 h), while the conjugates (as exemplified for 30) are accumulating in the endoplasmic reticulum but not in the mitochondria. The development of safirinium–hybrids targeting the endoplasmic reticulum can be regarded as a promising strategy in the development of cytotoxic agents.

COMPOSITIONS AND METHODS FOR TREATMENT OF PLATINUM-BASED CHEMOTHERAPEUTIC RESISTANT TUMORS

Embodiments of the instant disclosure relate to novel methods and compositions for treating tumors resistant to platinum-based chemotherapy. In certain embodiments, methods of treating tumors herein can include administering an effective amount of at least one ursolic acid derivative. In certain embodiments, methods of treating tumors herein can include administering an effective amount of at least one ursolic acid derivative in combination with at least one platinum-based chemotherapeutic separately or in a combination therapy. In some embodiments, methods of treating tumors disclosed herein can include screening and/or selecting a subject suitable for treatment on the basis of SENP1 tumor expression. In other embodiments, methods of treating tumors can include administering a composition disclosed herein to a subject, the composition having a combination of at least one ursolic acid derivative and at least one platinum-based chemotherapeutic.

The presence of a cyclohexyldiamine moiety confers cytotoxicity to pentacyclic triterpenoids

Pentacyclic triterpenoids oleanolic acid, ursolic acid, betulinic acid, and platanic acid were acetylated and converted into several amides 9–31; the cytotoxicity of which has been determined in sulforhodamine B assays employing seral human tumor cell lines and nonmalignant fibrob-lasts. Thereby, a betulinic acid/trans-1,4-cyclohexyldiamine amide showed excellent cytotoxicity (for example, EC50 = 0.6 μM for HT29 colon adenocarcinoma cells).

Design, Synthesis and Biological Activity of C3 Hemisynthetic Triterpenic Esters as Novel Antitrypanosomal Hits

Research for innovative drugs is crucial to contribute to parasitic infections control and eradication. Inspired by natural antiprotozoal triterpenes, a library of 12 hemisynthetic 3-O-arylalkyl esters was derived from ursolic and oleanolic acids through one-step synthesis. Compounds were tested on Trypanosoma, Leishmania and the WI38 cell line alongside with a set of triterpenic acids. Results showed that the triterpenic C3 esterification keeps the antitrypanosomal activity (IC50≈1.6–5.5 μm) while reducing the cytotoxicity compared to parent acids. Unsaturation of the ester alkyl chain leads to an activity loss interestingly kept when a sterically hindered group replaces the double bond or shields the ester group. An ursane/oleanane C3 hydroxylation was the only important feature for antileishmanial activity. Two candidates, dihydrocinnamoyl and 2-fluorophenylpropionyl ursolic acids, were tested on an acute mouse model of African trypanosomiasis with significant parasitemia reduction at day 5 post-infection for the dihydrocinnamoyl derivative. Further evaluation on other alkyl/protective groups should be investigated both in vitro and in vivo.

Acetoxyl ursolic acid piperazine compound containing isopropanolamine substructure, and preparation method and application of acetoxyl ursolic acid piperazine compound

The invention relates to an acetoxyl ursolic acid piperazine compound containing an isopropanolamine substructure, and a preparation method and application of the acetoxyl ursolic acid piperazine compound. The compound has a structure disclosed in a following general formula (I): an ursolic acid compound is taken as a basis, a nitrogen-containing fragment is introduced into the system to synthesize one series of 3[beta]-acetoxyl ursolic acid-28-piperazine compound containing the isopropanolamine substructure, and the compound has a good inhibition effect on plant pathogenic bacteria, includingxanthomonas oryzaepv. oryzae, xanthomonas axonopodis pv. Citri and the like.

The presence of a cationic center is not alone decisive for the cytotoxicity of triterpene carboxylic acid amides

3-O-Acetyl-ursolic acid (2) and 3-O-acetyl oleanolic acid (8) were converted into piperazinylamides holding a distal NH, NMe or a NMe2 group. These compounds as well as the corresponding N-methyl-N-oxides were accessed. Their cytotoxicity was assessed in SRB assays employing a panel of human tumor cell lines and non-malignant fibroblasts (NIH 3T3). As a result, compounds holding a quaternary distal N-substituent were less cytotoxic that those holding a NH-moiety. Hence, the presence of a distal cationic center seems not to be a sufficient criterion for obtaining triterpenoids of high cytotoxicity and selectivity.