10538-55-3Relevant articles and documents
p-Toluenesulfonic acid/methanol: mild reagent for the preparation of bile acid methyl esters.
Dayal,Speck,Bagan,Tint,Salen
, p. 239 - 242 (1981)
An improved method for the preparation of bile acid methyl esters is described. This is achieved by the addition of catalytic amounts of p-toluenesulfonic acid in a solution of bile acid in methanol. Advantages of this procedure over conventional methods include (1) use of a mild solid acid catalyst which prevents the formation of undesirable byproducts, (2) isolation of a solid product of high purity and (3) utilization of a relatively safe reagent in comparison to other methods involving diazomethane, hydrochloric acid or sulfuric acid.
Synthesis and characterization of organometallic rhenium(I{cyrillic, ukrainian}) and technetium(I{cyrillic, ukrainian}) bile acid complexes
Huang, Liliang,Zhu, Hua,Xu, Xiaoping,Zhang, Chunchun,Shen, Yu-Mei
, p. 3247 - 3253 (2009)
Eight bile acid derivatives have been synthesized with alkyl chains of various length based tridentate ligand chelating system. These derivatives have been reacted with the precursor [Et4N]2[Re(CO)3Br3] and fac-[M(CO)3(H2O)3]+ (M = 99mTc, Re) in ethanol or ethanol-aqueous media to form water-soluble and stable organometallic complexes in good yields. 1H NMR, 13C NMR, IR and elemental analysis or HRMS spectroscopic analyses confirmed the tridentate complexation of the metal-tricarbonyl fragment exclusively via the tridentate chelates. In addition, the corresponding radioactive technetium-99m complexes were prepared successfully and challenged for stability in physiological phosphate buffer at 37 °C for 24 h. No decomposition of the complexes could be detected under the condition proving the stability of these complexes.
Microwave-induced organic reactions of bile acids: Esterification, deformylation and deacetylation using mild reagents
Dayal, B.,Rao, Keshava,Salen, G.
, p. 453 - 457 (1995)
An efficient and convenient procedure for the esterification, deformylation, and deacetylation of bile acids is described.This is achieved by the addition of a catalytic amount of methanesulfonic acid or para-toluene sulfonic acid to a solution of bile acid in methanol in the domestic microwave oven.All these reactions were completed in the microwave oven within 1-3 min at 60percent power (390 W) and the desired bile acids, namely trihydroxy-5β-cholestanoic acid, (23R)-3α,7α,23-trihydroxy-5β-cholan-24-oic acid, ursocholic acid and 7-ketolithocholic acid were isolated in 86-94percent yield. - Keywords: microwave; bile acids; esterification; deformylation; deacetylation; methanesulfonic acid/methanol; para-toluene sulfonic acid/methanol
Corrigendum to "Synthesis and antimicrobial evaluation of bile acid tridentate conjugates" [Steroids 74 (2009) 701-706] (DOI:10.1016/j.steroids.2009.03.005)
Huang, Liliang,Sun, Yanhong,Zhu, Hua,Zhang, Yuanqing,Xu, Jia,Shen, Yu-Mei
, p. 189 - 189 (2010)
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Structural analysis and antitussive evaluation of five novel esters of verticinone and bile acids
Zhang, Jiu-liang,Wang, Hui,Pi, Hui-fang,Ruan, Han-li,Zhang, Peng,Wu, Ji-zhou
, p. 424 - 434 (2009)
Shedan-Chuanbei powder, a complex of traditional Chinese medicine preparation, which consists of Snake Bile (Chinese name "Shedan") and Fritillariae Cirrhosae (Chinese name "Chuanbei"), is the most popular antitussive and expectorant formulation in Chinese communities. However, the clinical application of Shedan-Chuanbei powder is now stringently limited because of the shortage of the two crude medicinal materials, especially for the sake of animal protection. In addition, the inherent defects of the most of the complex of traditional Chinese medicine such as the indistinct basal pharmacodynamic materials and the difficulties in quality control had blocked them heading into the international medicinal market. So we attempted to seek new substitute for Shedan-Chuanbei powder for antitussive drugs. In order to gain some new compounds with better bioactivity and attenuated toxicity, we tried to combine two kinds of drugs through ester bond. Enlightened with "combination principle" in drug discovery, we synthesized five novel esters of verticinone and bile acids, both of which are the major bioactive components in Shedan-Chuanbei powder. We then evaluated the antitussive activity and the acute toxicity of the five ester-linked compounds. The five ester-linked compounds had much more potent antitussive activity and expectorant activity than single bile acids at the same doses, and had equivalent antitussive activity and expectorant activity in comparison with about double moles dose of the monomer verticinone. Especially, cholic acid-verticinone ester had much more potent antitussive effects than the monomer verticinone or cholic acid at the same dose. A further acute toxicity study showed that the LD50 values of the five ester-linked compounds exceeded 3.5 g/kg by intraperitoneal injection in mice. Based on the studies of pharmacology and acute toxicity, the five ester-linked compounds have synergic pharmacodynamic action and attenuated toxicity compared with single verticinone and single bile acids.
SYNTHETIC DERIVATIVES OF CHOLIC ACID 7-SULFATE AND USES THEREOF
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Paragraph 00365-00366, (2020/07/05)
The compositions and methods provided herein are related, in part, to the discovery of cholic acid 7-sulfate as a treatment for diabetes. Provided herein is a method for treating a metabolic disorder (e.g., diabetes, obesity), or an inflammatory disease (e.g., Crohn's disease, inflammatory bowel disease, ulcerative colitis, pancreatitis, hepatitis, appendicitis, gastritis, diverticulitis, celiac disease, food intolerance, enteritis, ulcer, gastroesophageal reflux disease (GERD), psoriatic arthritis, psoriasis, and rheumatoid arthritis) in a subject in need thereof comprising administering to a subject a compound of Formulae (I)-(XVII).
Method for preparing ursodeoxycholic acid
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Paragraph 0006; 0024; 0025, (2018/03/25)
The invention provides a method for preparing ursodeoxycholic acid; with 7-carbonyl lithocholic acid ester as a raw material, a zinc powder/ammonium formate system is used for catalytic hydrogenation,hydrolysis and recrystallization to prepare ursodeoxycholic acid; the reaction routes and the process conditions are optimized, and the purity and the yield of the product are improved.
