1173-32-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Oxo-5β-24-cholanoic acid methyl ester is used as an intermediate in the synthesis of Taurolithocholic Acid (T009100) for its role in the development of pharmaceuticals. Taurolithocholic Acid is a major human metabolite and a bile acid that inhibits radioligand binding to muscarinic M1 receptors, making it a potential target for the treatment of various medical conditions related to muscarinic receptor dysfunction.
Used in Research and Development:
3-Oxo-5β-24-cholanoic acid methyl ester is utilized as a key compound in the research and development of new drugs and therapies. Its unique structure and properties make it a valuable tool for understanding the mechanisms of action and potential applications of related compounds in the field of medicinal chemistry.

Upstream product

• 1249-75-8 methyl lithocholate 
• 67-56-1 methanol 
• 1553-56-6 dehydrolithocholic acid 
• 73409-98-0 choladiene-1,4 one-3 oate-24 de methyle 
• 5405-42-5 methyl 3β-hydroxy-5β-cholan-24-oate 
• 91667-86-6 5β cholene-1, one-3, oate-24 de methyle 
• 20231-57-6 methyl 5-cholenoate 
• 1452-33-1 methyl 3-oxo-4-cholenolate 
• 186581-53-3 diazomethane 
• 434-13-9 Lithocholic acid 

Downstream Products

• 5405-42-5 methyl 3β-hydroxy-5β-cholan-24-oate 
• 1452-33-1 methyl 3-oxo-4-cholenolate 
• 148785-41-5 methyl 4β-acetoxy-3-oxo-5β-cholan-24-oate 
• 73409-98-0 choladiene-1,4 one-3 oate-24 de methyle 
• 91667-86-6 5β cholene-1, one-3, oate-24 de methyle 
• 1249-75-8 methyl lithocholate 
• 77285-18-8 methyl 3-ketocholanate tosylhydrazone 
• 643758-93-4 methyl 5β-hydroxy-3-oxocholan-24-oate 
• 501119-96-6 (R)-4-[(1R,3aS,3bR,5aR,10aS,10bS,12aR)-8-(3-Hydroxy-benzyl)-10a,12a-dimethyl-1,2,3,3a,3b,4,5,5a,6,8,10,10a,10b,11,12,12a-hexadecahydro-7,8-diaza-dicyclopenta[a,h]phenanthren-1-yl]-pentanoic acid 
• 501120-05-4 {(R)-4-[(1R,3aS,3bR,5aR,10aS,10bS,12aR)-8-(3-Hydroxy-benzyl)-10a,12a-dimethyl-1,2,3,3a,3b,4,5,5a,6,8,10,10a,10b,11,12,12a-hexadecahydro-7,8-diaza-dicyclopenta[a,h]phenanthren-1-yl]-pentanoylamino}-acetic acid tert-butyl ester 
• 1249-75-8 methyl 3β-hydroxy-5α-cholan-24-oate 
• 1258236-46-2 C₃₂H₄₆BrN₃O₂S 
• 1025965-86-9 Benzoic acid (R)-4-[(3R,3aR,5aS,6R,9aS,9bS)-6-(2-carboxy-ethyl)-3a,6-dimethyl-7-oxo-dodecahydro-cyclopenta[a]naphthalen-3-yl]-pentyl ester 
• 473462-28-1 24-(benzoyloxy)-chol-4-en-3-one 

Relevant academic research and scientific papers

Synthesis and characterization of lithocholic acid derived dipyrromethanes: Precursors for pyrrole-steroidal macrocycles

Three steroidal dipyrromethanes, 3,3,24,24-tetrakis(pyrrol-2-yl)-5β- cholane 1, 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oic acid 2, and methyl 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oate 3, have been prepared from 3α-hydroxy-5β-cholan-24-oic acid (lithocholic acid) 4 in good overall yields. The structures of 1-3 have been fully characterized by 1H, 13C, PFG DQF 1H-1H COSY, 1H- 1H ROESY, 13C DEPT-135, PFG 1H-13C HMQC, PFG 1H-13C HMBC, and PFG 1H- 15N HMBC NMR spectra. Their molecular weights and compositions have been determined by ESI-TOF and EI mass spectra, and elemental analyses. The energetically optimised geometry and isotropic 13C NMR chemical shifts of 3,3,24,24-tetrakis(pyrrol-2-yl)-5β-cholane 1 have been calculated by ab initio HF/6-31G* and DFT B3PW91/6-311G* methods.

Bile acid-derived mono- and diketals-synthesis, structural characterization and self-assembling properties

Three oxo-derivatives of bile acid methyl esters have been used as starting compounds in the preparation of novel bile acid monoketals with 1,2-benzenediol (catechol) and 2,3-naphthalenediol, as well as mono- and diketals with pentaerythritol. Monoketals of pentaerythritol showed a tendency to form thermoreversible gels in many aromatic solvents and the methyl lithocholate derivative proved to be a supergelator able to form a gel with t-butylbenzene at a concentration as low as 0.5% w/v. Whereas the naphthalenediol ketals formed film-type materials in the studied solvents, the catechol ketals underwent rapid crystallization into X-ray quality single crystals. Single crystal X-ray structures of the catechol ketals have been determined. The monoketal obtained from methyl-3,7,12-trioxo-5β-cholan-24-oate (dehydrocholate) revealed to have an unusual packing pattern in its solid state compared to other bile acid derivatives reported in the literature. The synthesis of diketals from pentaerythritol furnished a mixture of two diastereomers which, in the case of the methyl lithocholate derivative, have been separated and the X-ray crystal structure of one isomer resolved.

Spontaneous Ketalization of 3-Keto-5β-cholanic Acids in Methanol

The formation of 3-dimethyl ketals of 3-ketocholanic acids in methanol is described.The dependence of this unexpected behaviour on pKa of the cholanic acids is also reported.

NMDAR INHIBITING AGENTS AND GABAAR POTENTIATING AGENTS AND USES THEREOF

N-methyl-d-aspartate receptors (NMDAR) and/or potentiating y-aminobutyric acid receptors (GABAAR) agents and uses thereof are described. Uses of these agents include methods of treating or preventing various psychiatric diseases, disorders, or conditions and methods of treating or preventing alcohol use disorder in a subject in need thereof.

Cholic acid derivative and preparation method and application thereof

The invention discloses a cholic acid derivative represented by the formula (I) and a preparation method thereof. The target product cholic acid derivative is prepared by esterification, oxidation, bromination, debromination, 4,4-dimethylation, C-7 oxidation, reduction, TBSCl protection, iodation, cyano substitution, Wittig, Grignard, TBS-removing protection and other reactions. The invention alsoprovides an application of the cholic acid derivative in inhibiting cholesterol synthesis and reducing cholesterol and triglyceride levels in a body; the cholic acid derivative can be used for preparing drugs for preventing and treating hypercholesterolemia, hypertriglyceride, atherosclerosis and other diseases, and has good application prospects.

Counteracting in Vitro Toxicity of the Ionophoric Mycotoxin Beauvericin - Synthetic Receptors to the Rescue

Beauvericin (BEA) and enniatins are toxic ionophoric cyclodepsipeptides that mainly occur in grains. As such, their presence in food commodities poses a concern for public health. To date, despite recent European Food Safety Authority emphasis on the need for more data to evaluate long-term toxicity effects, no suitable affinity reagents are available to detect the presence of BEA and derivatives in food samples. We here report on the synthesis of a small library of artificial receptors with varying cavity sizes and different hydrophobic building blocks. Immobilization of one of the receptors on solid support resulted in a strong retention of beauvericin, thus revealing promising properties as solid-phase extraction material for sample pretreatment. Furthermore, treatment of HepG2 cells with the most promising receptor markedly reduced beauvericin-induced cytotoxicity, hinting toward the possibility of using synthetic receptors as antidotes against ionophoric toxins.

SYNTHETIC RECEPTORS FOR IONOPHORIC COMPOUNDS

The present invention relates to synthetic receptors for ionophoric compounds, such as ionophoric toxins. Hence, the invention provides synthetic molecules capable of binding different ionophoric compounds, thereby being suitable for use in the detection,

Cholesterol molecular probe as well as preparation method and application thereof

The invention discloses a cholesterol molecular probe and a preparation method thereof. The cholesterol molecular probe shown as a formula (I) is prepared by taking lithocholic acid as a raw material through esterification reaction, oxidization reaction, dehydrogenation reaction, carbonyl protection reaction, reduction reaction, hydroxyl protection reaction, reduction reaction, iodination reaction, substitution reaction and de-protection reaction. The invention further discloses application of the cholesterol molecular probe shown as the formula (I) to identification of cholesterol modified protein. The cholesterol molecular probe provided by the invention can be used for simulating normal cholesterol to promote cell growth, and prompting the shearing ripening of the cholesterol modified protein hedgehog, and can also be used for researching cholesterol modification of the protein.

Lithocholic acid and derivatives: Antibacterial activity

In order to develop bioactive lithocholic acid derivatives, we prepared fifteen semi-synthetic compounds through modification at C-3 and/or C-24. The reactions showed yields ranging from 37% to 100%. The structures of all compounds obtained were identified on the basis of their spectral data (IR, MS, 1D- and 2D-NMR). The activity of lithocholic acid and derivatives was evaluated against the growth of Escherichia coli, Staphylococcus aureus, Bacillus cereus and Pseudomonas aeruginosa. The derivative 3α-formyloxy-5β-cholan-24-oic acid (LA-06) showed the best activity, with MIC values of 0.0790 mM against E. coli (Ec 27) and B. cereus in both cases, and 0.0395 mM against S. aureus (ATCC 12692). Lithocholic acid and the derivatives with MIC ≤ 1.2 mM were evaluated on the susceptibility of some bacterial pathogens to the aminoglycoside antibiotics neomycin, amikacin and gentamicin was evaluated. There are no previously reported studies about these compounds as modifiers of the action of antibiotics or any other drugs.

First synthesis of steroidal 1,2,4-trioxolanes

Griesbaum ozonolysis of mixtures of methyl 3-(methoxyimino)-5β-cholan- 24-oate with ketones (cyclohexanone, methyl trifluoromethyl ketone, and phenyl trifluoromethyl ketone) afforded for the first time steroidal 1,2,4-trioxolanes which were isolated as mixtures of stereoisomers.