10573-17-8Relevant academic research and scientific papers
Potential bile acid metabolites. 20. A new synthetic route to stereoisomeric 3,6,-dihydroxy-and 6-hydroxy-5α-cholanoic acids
Iida, Takashi,Tamaru, Tamaaki,Chang, Frederic C.,Niwa, Toshifumi,Goto, Junichi,Nambara, Toshio
, p. 362 - 369 (1993)
An improved procedure for the syntheses of stereoisomeric 3,6,-dihydroxy- and 6-hydroxy-5α-cholanoic acids (and their methyl esters) is described. The principal reactions emplyoed are those reported in the preceding paper of this series, with the commercially available hyodeoxycholic acid as starting material. The final step in the procedure is the reduction of the key 5α C-6 ketones with either the stereoselective equatorial reagent, Li/NH3/MeOH, or the axial reagent, Zn(BH4)2). The results of analysis of the prepared 6-monohydroxylated and 3,6-dihydroxylated stereoisomers by thin-layer chromatographic, high performance liquid chromatographic and gas-liquid chromatographic mobilities, and 1H and 13C nuclear magnetic resonance spectra are discussed along with the dat for the corresponding compounds in the 5β-series. (Steroids 58: 362-369, 1993).
GPBAR1 activation by C6-substituted hyodeoxycholane analogues protect against colitis
De Marino, Simona,Finamore, Claudia,Biagioli, Michele,Carino, Adriana,Marchiano, Silvia,Roselli, Rosalinda,Di Giorgio, Cristina,Bordoni, Martina,Di Leva, Francesco Saverio,Novellino, Ettore,Cassiano, Chiara,Limongelli, Vittorio,Zampella, Angela,Festa, Carmen,Fiorucci, Stefano
, p. 818 - 824 (2020)
GPBAR1 agonists have been identified as potential leads for the treatment of diseases related to colon inflammation such as Crohn's and ulcerative colitis. In this paper, we report the discovery of a small library of hyodeoxycholane analogues, decorated at C-6 with different substituents, as potent and selective GPBAR1 agonists. In vitro pharmacological assays showed that compound 6 selectively activates GPBAR1 (EC50 = 0.3 μM) and reduces the production of pro-inflammatory cytokines (IL-1β, IL-6, and TNF-a) in THP1 cells. The binding mode of compound 6 in GPBAR1 was elucidated by docking calculations. Moreover, compound 6 protects against TNBSinduced colitis in Gpbar1+/+ rodent model, representing an intriguing lead for the treatment of these inflammatory disorders.
Preparation method of 3-hydroxy-6-ketocholanic acid with low cost and high yield
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Paragraph 0036-0041, (2020/06/20)
The invention discloses a preparation method of 3 alpha-hydroxy-6-keto-5 beta-cholestane-24-acid with low cost and high yield, which is characterized by comprising the following steps: adding hyodeoxycholic acid into a mixed solution of an organic solvent and water, and stirring to dissolve; adding bromide and acid, stirring and dissolving; bromate is added for reaction; adding a terminating agent, and stirring to terminate the reaction; adding water to crystallize the product; and carrying out solid-liquid separation, washing a solid product with water for multiple times, and drying to obtainthe 3 alpha-hydroxy-6-keto-5 beta-cholestane-24-acid. According to the method, a common and safe reagent is adopted, the hyodeoxycholic acid is selectively oxidized into the 3 alpha-hydroxy-6-keto-5beta-cholestane-24-acid under a relatively mild condition, the product purity is greater than 98.0%, and the yield is greater than 85%. The method has the advantages of cheap reagents, simple operation, high process reproducibility, simple post-treatment, high product purity and high yield, and can easily implement industrial production.
Synthetic method for 6-carbonyl lithocholic acid
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, (2019/02/19)
The invention discloses a synthetic method for 6-carbonyl lithocholic acid. The synthetic method comprises the following steps of by adopting hyodeoxycholic acid as a starting material, sequentially performing 4-step reaction of 24-carboxyl esterification, oxidization of 3 alpha-OH and 6 alpha-OH into carbonyl groups, selective reduction and hydrolyzation to obtain a target product. The synthetictechnology is simple in flow, liable to control, wide in raw material source and available in raw material and can realize mass production.
Method for synthesizing lithocholic acid from hyodesoxycholic acid
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Paragraph 0036; 0037; 0038; 0039, (2017/08/29)
The invention discloses a method for synthesizing lithocholic acid, comprising: using hyodesoxycholic acid as a start material, and performing two-step reaction of 6Alpha-OH selective oxidation and Huang Minglon reduction to synthesize the lithocholic acid. The start material herein is low in price and easy to obtain, the synthetic steps are short, posttreatment is simple, few side reactions are employed, and the method is applicable to industrial production.
Structural modifications of deoxycholic acid to obtain three known brassinosteroid analogues and full NMR spectroscopic characterization
Herrera, Heidy,Carvajal, Rodrigo,Olea, Andrés F.,Espinoza, Luis
, (2016/09/23)
An improved synthesis route for obtaining known brassinosteroid analogues, i.e., methyl 2α,3α-dihydroxy-6-oxo-5α-cholan-24-oate (11), methyl 3α-hydroxy-6-oxo-7-oxa-5α-cholan-24-oate (15) and methyl 3α-hydroxy-6-oxa-7-oxo-5α-cholan-24-oate (16), from hyodeoxycholic acid (4) maintaining the native side chain is described. In the alternative procedure, the di-oxidized product 6, obtained in the oxidation of methyl hyodeoxycholate 5, was converted almost quantitatively into the target monoketone 7 by stereoselective reduction with NaBH4 , increasing the overall yield of this synthetic route to 96.8%. The complete 1H- and 13C-NMR assignments for all compounds synthesized in this work have been made by 1D and 2D heteronuclear correlation gs-HSQC and gs-HMBC techniques. Thus, it was possible to update the spectroscopic information of 1H-NMR and to accomplish a complete assignment of all 13C-NMR signals for analogues 5-16, which were previously reported only in partial form.
