7727-82-4

Usage

InChI:InChI=1/C25H36O5/c1-14(5-8-22(29)30-4)17-6-7-18-23-19(13-21(28)25(17,18)3)24(2)10-9-16(26)11-15(24)12-20(23)27/h14-15,17-19,23H,5-13H2,1-4H3

Upstream product

• 81-23-2 dehydrocholic acid 
• 74-88-4 methyl iodide 
• 68138-89-6 (5S,9S,10S,13R,14S,17R)-17-((R)-4-iodobutan-2-yl)-10,13-dimethyldecahydro-1H-cyclopenta[a]phenanthrene-3,7,12(2H,4H,8H)-trione 
• 18414-58-9 diphenylmethylsilanecarboxylic acid 
• 865-34-9 lithium methanolate 
• 1346220-47-0 ¹³C-methyldiphenylsilanecarboxylic acid 
• 81-25-4 cholic acid 
• 1448-36-8 methyl cholate 
• 64-19-7 acetic acid 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 

Downstream Products

• 1600520-70-4 N-benzyl-N-methyl-3α,7α,12α-tris[(phenylaminocarbonyl)amino]-5β-cholan-24-amide 
• 1600520-69-1 N,N-dimethyl-3α,7α,12α-tris[(phenylaminocarbonyl)amino]-5β-cholan-24-amide 
• 1600520-68-0 N-benzyl-3α,7α,12α-tris[(phenylaminocarbonyl)amino]-5β-cholan-24-amide 
• 1600520-67-9 N-methyl-3α,7α,12α-tris[(phenylaminocarbonyl)amino]-5β-cholan-24-amide 
• 1243065-14-6 3α,7α,12α-tris[(phenylaminocarbonyl)amino]-5β-cholic acid 
• 10538-64-4 methyl 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oate 
• 1553-56-6 dehydrolithocholic acid 
• 1448-36-8 methyl cholate 
• 25312-65-6 cholanic acid 

Relevant academic research and scientific papers

Nickel-Mediated Alkoxycarbonylation for Complete Carbon Isotope Replacement

Many commercial drugs, as well as upcoming pharmaceutically active compounds in the pipeline, display aliphatic carboxylic acids or derivatives thereof as key structural entities. Synthetic methods for rapidly accessing isotopologues of such compounds are highly relevant for undertaking critical pharmacological studies. In this paper, we disclose a direct synthetic route allowing for full carbon isotope replacement via a nickel-mediated alkoxycarbonylation. Employing a nickelII pincer complex ([(N2N)Ni-Cl]) in combination with carbon-13 labeled CO, alkyl iodide, sodium methoxide, photocatalyst, and blue LED light, it was possible to generate the corresponding isotopically labeled aliphatic carboxylates in good yields. Furthermore, the developed methodology was applied to the carbon isotope substitution of several pharmaceutically active compounds, whereby complete carbon-13 labeling was successfully accomplished. It was initially proposed that the carboxylation step would proceed via the in situ formation of a nickellacarboxylate, generated by CO insertion into the Ni-alkoxide bond. However, preliminary mechanistic investigations suggest an alternative pathway involving attack of an open shell species generated from the alkyl halide to a metal ligated CO to generate an acyl NiIII species. Subsequent reductive elimination involving the alkoxide eventually leads to carboxylate formation. An excess of the alkoxide was essential for obtaining a high yield of the product. In general, the presented methodology provides a simple and convenient setup for the synthesis and carbon isotope labeling of aliphatic carboxylates, while providing new insights about the reactivity of the N2N nickel pincer complex applied.

1,3-Dibromo-5,5-dimethylhydantoin as a Precatalyst for Activation of Carbonyl Functionality

Activation of carbonyl moiety is one of the most rudimentary approaches in organic synthesis and is crucial for a plethora of industrial-scale condensation reactions. In esterification and aldol condensation, which represent two of the most important reactions, the susceptibility of the carbonyl group to nucleophile attack allows the construction of a variety of useful organic compounds. In this context, there is a constant need for development of and improvement in the methods for addition-elimination reactions via activation of carbonyl functionality. In this paper, an advanced methodology for the direct esterification of carboxylic acids and alcohols, and for aldol condensation of aldehydes using widely available, inexpensive, and metal-free 1,3-dibromo-5,5-dimethylhydantoin under neat reaction conditions is reported. The method is air- and moisture-tolerant, allowing simple synthetic and isolation procedures for both reactions presented in this paper. The reaction pathway for esterification is proposed and a scale-up of certain industrially important derivatives is performed.

Esterification of aryl/alkyl acids catalysed by n-bromosuccinimide under mild reaction conditions

N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterification of aryl and alkyl carboxylic acids. Comprehensive esterification of substituted benzoic acids, mono-, di- and tri-carboxy alkyl derivatives has been performed under neat reaction conditions. The method is metal-free, air- and moisture-tolerant, allowing for a simple synthetic and isolation procedure as well as the large-scale synthesis of aromatic and alkyl esters with yields up to 100%. Protocol for the recycling of the catalyst has been proposed.

Cholanamide components for organic alloys; Expanding the scope of nanoporous steroidal ureas

Amide-linked side-chains can substitute for esters in crystalline nanoporous steroidal ureas (NSPUs). This efficient conjugation method increases the versatility of NPSUs, and should aid the inclusion of complex functional units in the crystal channels. The Royal Society of Chemistry 2014.

Synthesis of cholic acid amino analogues by oxime reduction with TiCl 3-NaBH3CN

Amino analogues of cholic acid have been synthesized by reduction of the corresponding oximes with titanium(iii) chloride in the presence of sodium cyanoborohydride.

Synthesis of Amino analogues of cholic acid

Amino analogues of cholic acid were synthesized by reduction of oximes using titanium(III) chloride in the presence of sodium cyanoborohydride. Pleiades Publishing, Ltd., 2011.

Synthesis and cytotoxicity of A-homo-lactam derivatives of cholic acid and 7-deoxycholic acid

Using cholic acid and deoxycholic acid as starting materials, a series of 3-aza-A-homo-4-one bile acid and 7-deoxycholic acid derivatives were synthesized by the esterification, oxidation, reduction, oximation and Beckman rearrangement etc. The cytotoxicity of the synthesized compounds against MGC 7901 (human ventriculi carcinoma cell line), hela (human cervical carcinoma cell line), SMMC 7404 (human liver carcinoma cell line) were investigated. The results showed that bile acid and 7-deoxycholic-acid derivatives with 3-aza-A-homo-4-one configuration bearing a 6-hydroximino or 12-hydroximino group displayed a distinct cytotoxicity to Hela tumor cell line. In particular, the IC50 values of the compounds 6 and 13 were 14.3 and 24.3 μmol/L against Hela human tumor cell line respectively. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs.

CATIONIC STEROID ANTIMICROBIAL DIAGNOSTIC, DETECTION, SCREENING AND IMAGING METHODS

The invention relates to diagnostic, detection, screening and imaging methods. In various embodiments, methods of diagnosis, detection, screening and imaging include administering a cationic steroid antimicrobial or CSA to a subject having or at risk of having an infection or a hyperproliferative disorder (e.g., a tumor, cancer or neoplasia) in an amount effective to diagnose or detect the infection or the hyperproliferative disorder (e.g., a tumor, cancer or neoplasia) in the subject. In a particular aspect, a detectable CSA, namely CSA- 13 labeled with 99mTc is used to detect the presence of an infection.

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.

Cationic Steroid Antimicrobial Compositions and Methods of Use

The invention provides methods for decreasing or inhibiting poxvirus infection or pathogenesis of a cell in vitro, ex vivo or in vivo, a symptom or pathology associated with poxvirus infection or pathogenesis in vitro, ex vivo or in vivo, or an adverse side effect of poxvirus infection or pathogenesis in vitro, ex vivo or in vivo. In one embodiment, a method of the invention includes treating a subject with an invention compound (e.g., cationic steroid antimicrobial or CSA).