2868-48-6Relevant academic research and scientific papers
Synthesis of 5α-cholestan-6-one derivatives and their inhibitory activities of NO production in activated microglia: Discovery of a novel neuroinflammation inhibitor
Yang, Ya-Xi,Zheng, Long-Tai,Shi, Jing-Jing,Gao, Bo,Chen, Yan-Ke,Yang, Hui-Chi,Chen, Hong-Li,Li, Yuan-Chao,Zhen, Xue-Chu
, p. 1222 - 1227 (2014)
Glial activation-mediated neuroinflammation plays a pivotal role in the process of several neuroinflammatory diseases including stroke, Alzheimer's diseases, Parkinson's diseases, multiple sclerosis and ischemia. Inhibition of microglial activation may ameliorate neuronal degeneration under the inflammatory conditions. In the present study, a number of 5α-cholestan-6- one derivatives were prepared and the anti-inflammatory effects of these compounds were evaluated in LPS-stimulated BV-2 microglia cells. Those derivatives were synthesized from readily available hyodeoxycholic acid (1). Among the tested compounds, several analogs (16-18, 25, 35, 38) exhibited potent inhibitory activities on nitric oxide production with no or weak cell toxicity. Compound 16 also significantly suppressed the expression of TNF-α, interleukin (IL)-1β, cyclooxygenase (COX-2) as well as inducible nitric oxide synthase (iNOS) in LPS-stimulated BV-2 microglia cells. In addition, compound 16 markedly reduced infarction volume in a focal ischemic mice model.
Preparation method of chenodeoxycholic acid
-
Paragraph 0089-0096; 0151-0153, (2021/01/24)
The invention relates to the technical field of medicine synthesis, in particular to a preparation method of chenodeoxycholic acid. The invention develops a method for synthesizing the chenodeoxycholic acid by taking hyodeoxycholic acid(3alpha, 6alpha-dihydroxy-5beta-cholanic acid)as a raw material through nine steps of reaction, the reaction conditions of each step are mild, the control is easy,the process is simple, the used raw materials are wide in source, low in price and easy to obtain, the yield is high, the total yield can reach 61%, the synthesis cost is low, and the method is suitable for mass preparation and industrial production.
METHOD FOR HOMOGENIZING BILE ACID DERIVATIVES
-
Paragraph 0083-0085, (2021/05/28)
The present invention relates to a process for producing bile acid derivatives having a protected hydroxyl group in the 3 position comprising contacting a bile acid derivative having an unprotected 3-alpha-hydroxyl group with a specific lipase. The present invention further relates to a bile acid derivative obtained or obtainable by the process, to the use of the bile acid derivative obtained or obtainable by the process for producing lithocholic acid and also to a process for producing lithocholic acid and to lithocholic obtained by the process. The invention further relates to the use of lithocholic acid obtained or obtainable by the process for producing ursodeoxycholic acid or ursodeoxycholic acid derivatives.
Synthesis and biological activity of cyclopropyl Δ7-dafachronic acids as DAF-12 receptor ligands
Carotti, Andrea,Ceccarelli, Giada,Gioiello, Antimo,Goracci, Laura,Mancino, Valentina,Passeri, Daniela,Pellicciari, Roberto,Sardella, Roccaldo
, p. 5403 - 5412 (2021/06/30)
The four cyclopropyl stereoisomers of Δ7-dafachronic acids were prepared from the bile acid hyodeoxycholic acid and employed as chemical tools to exploit the importance of the orientation and spatial disposition of the carboxyl tail and the C25-methyl gro
Efficient synthesis of cholic acid derivates through stereoselective C–H functionalization from hyodeoxycholic acid
Liang, Yu-Yan,Huang, Huan,Li, Yang,Du, Rong-Kai,Li, Jing,Liu, Yong-Hong,Li, Shan,Zhang, Lei
, (2020/02/26)
Five cholic acid derivatives (including allo-ω-muricholic acid and CDCA) were synthesized from hyodeoxycholic acid via selective oxidation of C3- or C6-hydroxyl groups by IBX and NBS oxidants and stereocontrolled conversion. The hydroxyl group could be introduced through hydrolyzing α-Br keto with K2CO3 aqueous solution or through oxidizing the double bond by monoperoxyphthalic acid. The reduction of C6-O6 carbonyl to methylene could undergo with PTSH, NaBH3CN and ZnCl2 only at 5β configuration. A feasible synthetic route of CDCA from HDCA has been established to avoid the epimerization with the yield of 45% (8 steps). These strategies provided good yields, stereoselectivity and reproducibility for the preparation of cholic acid derivates and CDCA.
Synthesis of new cisplatin derivatives from bile acids
?otowski, Zenon,Hryniewicka, Agnieszka,Morzycki, Jacek W.,Rárová, Lucie,Seroka, Barbara,Sicinski, Rafal R.,Tomkiel, Aneta M.
, (2020/02/18)
A series of bile acid derived 1,2- and 1,3-diamines as well as their platinum(II) complexes were designed and synthesized in hope to get a highly cytotoxic compound by the combination of two bioactive moieties. All complexes obtained were subjected to cytotoxicity assays in vitro and some hybrid molecules showed an expected activity.
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
supporting information, p. 818 - 824 (2020/07/02)
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.
Method for synthesizing lithocholic acid from hyodeoxycholic acid as raw material
-
Paragraph 0021; 0029, (2019/01/23)
The invention discloses a method for synthesizing a lithocholic acid from a hyodeoxycholic acid as the raw material. The hyodeoxycholic acid is used as the starting material, the lithocholic acid is produced through the seven reaction steps of 24-carboxylesterification, carboxylation of 3alpha-hydroxyl and 6alpha-hydroxyl through oxidation, selective reduction, acylation, hydrazone formation, hydrazoneremoval, and hydrolysis. The starting material is cheap and easy to get, no hydrazine hydrate is used in the synthesis process, the technological conditions for synthesis are safe, environmentally friendly and mild, the total yield is relatively high, and the method is suitable for industrial production.
1,3-Dibromo-5,5-dimethylhydantoin as a Precatalyst for Activation of Carbonyl Functionality
?ebular, Klara,Bo?i?, Bojan ?.,Stavber, Stojan
supporting information, (2019/08/01)
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.
Synthetic method for 6-carbonyl lithocholic acid
-
Paragraph 0026; 0031, (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.
