cas 2868-48-6, HYODEOXYCHOLIC ACID METHYL ESTER

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Synthesis of 5α-cholestan-6-one derivatives and their inhibitory activities of NO production in activated microglia: Discovery of a novel neuroinflammation inhibitor
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.
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)
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Preparation method of chenodeoxycholic acid
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.
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Paragraph 0089-0096; 0151-0153

(2021/01/24)

METHOD FOR HOMOGENIZING BILE ACID DERIVATIVES
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.
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Paragraph 0083-0085

(2021/05/28)

Synthesis and biological activity of cyclopropyl Δ7-dafachronic acids as DAF-12 receptor ligands
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
Carotti, Andrea,Ceccarelli, Giada,Gioiello, Antimo,Goracci, Laura,Mancino, Valentina,Passeri, Daniela,Pellicciari, Roberto,Sardella, Roccaldo
p. 5403 - 5412
(2021/06/30)

Efficient synthesis of cholic acid derivates through stereoselective C–H functionalization from hyodeoxycholic acid
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.
Liang, Yu-Yan,Huang, Huan,Li, Yang,Du, Rong-Kai,Li, Jing,Liu, Yong-Hong,Li, Shan,Zhang, Lei
(2020/02/26)

Synthesis of new cisplatin derivatives from bile acids
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.
?otowski, Zenon,Hryniewicka, Agnieszka,Morzycki, Jacek W.,Rárová, Lucie,Seroka, Barbara,Sicinski, Rafal R.,Tomkiel, Aneta M.
(2020/02/18)

GPBAR1 activation by C6-substituted hyodeoxycholane analogues protect against colitis
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.
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)

Method for synthesizing lithocholic acid from hyodeoxycholic acid as raw material
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.
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Paragraph 0021; 0029

(2019/01/23)

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.
?ebular, Klara,Bo?i?, Bojan ?.,Stavber, Stojan
supporting information

(2019/08/01)

Synthetic method for 6-carbonyl lithocholic acid
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.
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Paragraph 0026; 0031

(2019/02/19)

Preparation method of muricholic acid
The invention relates to the technical field of drug synthesis, in particular to a preparation method of muricholic acid. According to the preparation method of the muricholic acid, 3[alpha], 6[alpha]-dyhydroxy-5[beta]-cholanic acid are used as raw materials for to be subjected to alkyl esterification, site-3 and site-6 selective oxidation is performed, a bromination reaction is performed, a substitution reaction is performed, site-6 reduction is performed, and hydrolysis is performed to obtain the muricholic acid. The muricholic acid is prepared by the synthetic route, namely 3[alpha], 6[beta], 7[beta]-trihydroxy-5[alpha]-cholanoic acid, a raw material source is wide, and sufficient supply is achieved; and the yield of the muricholic acid obtained by the steps is high and up to 24.5%, andthe muricholic acid is suitable for large-scale preparation and can provide data support and reference for subsequent related researches.
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Paragraph 0056-0063; 0100-0105

(2019/03/06)

HYODEOXYCHOLIC ACID DERIVATIVES AND USE THEREOF
The present invention concerns compounds having formula (I) and compositions thereof with a pharmacologically acceptable excipient and uses thereof as a medicament, in particular for the treatment and/or prevention of a disorder selected from the group consisting of: gastrointestinal disorders, liver diseases, cardiovascular and vascular diseases, pulmonary and metabolic diseases, infectious diseases, cancer, renal disorders, inflammatory disorders comprising immune mediated disorders, and neurological disorders.
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Page/Page column 20; 21

(2018/02/03)

A concise synthesis of 25-Hydroxycholesterol from hyodesoxycholic Acid
A simple, efficient and economical method has been developed for the synthesis of 25-hydroxycholesterol in seven steps from hyodesoxycholic acid with an overall yield of 39%. The preparation of the 3β-tetrahydropyranyloxychol-5-en-24-al from 3β-tetrahydropyranyloxychol-5-en-24-oic acid methyl ester with di-isobutylaluminium hydride was achieved instead of using the conventional two-step reaction, thus avoiding the use of the toxic oxidant CrO3. The terminal product was obtained by hydroxybromination of desmosterol with N-bromosuccinimide/H2O, followed by reduction and deprotection of the halohydrins with LiAlH4. This simplified route gave an increased overall yield and used economical and environmentally benign reagents.
Jin, Can,Wang, Yulei,Sun, Bin,Su, Weike
p. 96 - 99
(2018/03/21)

OXYSTEROLS AND METHODS OF USE THEREOF
Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R2, R3, R4, R5, and and R6 are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.
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Paragraph 00750

(2018/05/16)

Preparation method of obeticholic acid and intermediate thereof
The invention discloses a preparation method of obeticholic acid and an intermediate thereof. The invention provides a preparation method of a compound V. The preparation method of the compound V comprises the following steps: carrying out hydroxyl protective reaction on a compound VI and a hydroxyl protective reagent to obtain the compound V. The preparation method is simple and convenient to operate, low in cost, gentle in condition, environmentally friendly and suitable for industrialization.
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Paragraph 0219; 0220; 0221

(2018/07/30)

Preparation method of obeticholic acid and intermediate thereof
The invention discloses a preparation method of obeticholic acid and an intermediate thereof. The provided preparation method of the obeticholic acid comprises the following step: carrying out oxidizing reaction on a compound V and an oxidizing agent in an organic solvent to obtain a compound IV so as to obtain the final product. PG1 is a carboxyl protecting group, PG2 is a hydroxyl protecting group, and a component as shown in specification in the compound V and the compound IV independently shows that the ethidine is an E configuration, a Z configuration or a mixture of the E configuration and the Z configuration. The preparation method is simple and convenient to operate, low in cost, gentle in condition, environmentally friendly and suitable for industrialization.
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Paragraph 0220; 0221; 0222

(2018/07/30)

COMPOSITIONS AND METHODS FOR TREATING CLOSTRIDIUM ASSOCIATED DISEASES
The present disclosure provides compounds for preventing, treating, and/or reducing the risk of developing a Clostridium-associated disease in a mammalian subject. Also provided are pharmaceutically acceptable salts of such compounds and compositions that include such compounds and/or pharmaceutically acceptable salts thereof.
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Page/Page column 43-44

(2017/09/08)

Method for preparing ursodeoxycholic acid
The invention belongs to the field of medicine, and particularly relates to a method for preparing an ursodeoxycholic acid. The method comprises the following steps: performing esterification reaction to obtain a compound shown in formula II by taking an HDCA (hyodeoxycholic acid) as a starting raw material; performing selective hydroxy protection reaction to obtain a compound shown in formula III; performing hydroxy protection reaction to obtain a compound shown in formula IV; performing elimination reaction to obtain a compound shown in formula V; performing oxidation reaction on the compound shown in formula V under the action of tert-butyl hydroperoxide and pyridinium chlorochromate to obtain a compound shown in formula VI; performing hydrolysis to obtain a compound shown in formula VII; performing reduction to obtain the ursodeoxycholic acid shown in formula I. According to the method, the ursodeoxycholic acid is prepared by taking the HDCA as the starting raw material, so that not only can the problem of raw material shortage be solved, but also the method is convenient to operate, low in byproduct rate and cost, mild in reaction condition and suitable for large-scale production of the ursodeoxycholic acid.
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Paragraph 0062; 0063

(2017/07/20)

Obeticholic acid preparation method
The invention discloses an obeticholic acid preparation method, which comprises that (1) hyodeoxycholic acid II reacts with an alcohol compound III under the action of a catalyst to generate an ester compound IV; (2) the ester compound IV is subjected to PDC oxidation in dichloromethane to generate a compound V; (3) the compound V and trimethyl chlorosilane are subjected to a reaction at a temperature of -70 to -20 DEG C in tetrahydrofuran by using lithium diisopropylamide as an alkali to generate a silyl enol ether compound VI; (4) the silyl enol ether compound VI is subjected to m-chloroperoxybenzoic acid oxidation and deprotection in dichloromethane to generate a compound VII: (5) the compound VII and Yield generated from ethyltriphenylphosphonium bromide under the action of a strong alkali are subjected to a Wittig alkenylation reaction at a temperature of 0-70 DEG C to convert the ketone into the vinyl so as to generate a compound VIII; (6) the double bond of the compound VIII is subjected to catalytic hydrogenation reduction in a mixing solvent to generate a compound IX; and (7) the compound IX is hydrolyzed under an alkaline condition to generate the obeticholic acid.
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Paragraph 0047; 0048; 0049; 0050; 0051

(2017/10/28)

A method for preparing aobeiAobei cholic acid (by machine translation)
The invention belongs to the field of medicine, in particular relates to a preparation method of aobeiAobei cholic acid. The method is: to hyodeoxycholic acid HDCA as the starting raw material passes through the esterification reaction, the oxidation reaction, hydroxy protecting reaction, with bromoethane zinc oxide or diethyl zinc reagent reaction, dehydration reaction, oxidation reaction, reduction reaction and removing hydroxyl and carboxyl protection reaction to obtain aobeiAobei cholic acid. The method of the invention not only can solve the problem of raw materials, but also can avoid the strong alkaline and harsh reaction conditions such as high temperature, thereby greatly improving the aobeiAobei cholic acid synthesis efficiency, thus provides a few by-products, the operation is simple, mild reaction conditions, low cost, and is suitable for mass production aobeiAobei cholic acid new preparation method. (by machine translation)
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Paragraph 0071; 0072

(2017/07/21)

A Facile Route to Ursodeoxycholic Acid Based on Stereocontrolled Conversion and Aggregation Behavior Research
A facile route to ursodeoxycholic acid (UDCA) and its aggregation behavior in aqueous phase solution, which is rarely known, are reported. The starting material, hyodeoxycholic acid (HDCA), is a relatively less expensive material and more easily obtained compared with chenodeoxycholic acid (CDCA). A facile route was developed to synthesize UDCA from HDCA with a Shapiro reaction as the key step and in 26% overall yield. A new strategy using organosilane reagent considering its stability, nontoxicity, and abundance in nature was carried out for a more rapid route and higher yield. It was found that the critical micelle concentration value, which is a critical value for surfactants of bile salts, was influenced by the number of hydroxyl groups.
Dou, Qian,Jiang, Zhongliang
p. 588 - 594
(2016/02/14)

Structural modifications of deoxycholic acid to obtain three known brassinosteroid analogues and full NMR spectroscopic characterization
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.
Herrera, Heidy,Carvajal, Rodrigo,Olea, Andrés F.,Espinoza, Luis
(2016/09/23)

Novel 3,4-seco bile acid diamides as selective anticancer proliferation and migration agents
A series of new seco-A ring bile acid diamides were synthesized, and their antiproliferative activities against PC3M (prostate), HT29 (colon) and ES-2 (ovarian) cancer cell lines were investigated using SRB assays. Most synthesized compounds presented improved antiproliferative activities compared to the parent bile acids (IC50> 80 μM), especially the piperazine conjugated compound 27 with IC50values of 1.07, 4.58 and 3.86 μM against PC3M, HT29 and ES-2 cancer cell lines, respectively. In addition, all the tested compounds showed less cytotoxic activity on a noncancerous cell line (HAF), and the most active compound 27 exhibited the highest selectivity (Selectivity Index, SIPC3M= 26.3). Furthermore, 27 could also enhance G1 arrest in PC3M cell, revealed by cell cycle analysis, and increase anti-migration activity on PC3M cells, confirmed by transwell migration assay.
Mao, Shi-Wei,Chen, Huang,Yu, Li-Fang,Lv, Fang,Xing, Ya-Jing,Liu, Ting,Xie, Jia,Tang, Jie,Yi, Zhengfang,Yang, Fan
p. 574 - 583
(2016/07/22)

Design and synthesis of a crosslinker for studying intracellular steroid trafficking pathways
A crosslinker was designed and synthesized as a molecular tool for potential use in probing the intracellular trafficking pathways of steroids. The design was guided by computational modeling based upon a model for the transfer of cholesterol between two
Byrd, Katherine M.,Arieno, Marcus D.,Kennelly, Megan E.,Estiu, Guillermina,Wiest, Olaf,Helquist, Paul
p. 3843 - 3851
(2015/07/27)

NEUROACTIVE STEROIDS AND METHODS OF USE THEREOF
3beta, 17beta disubstituted steroidal compounds, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, are provided for the prevention and treatment of a variety of CNS-related conditions.
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Paragraph 00275

(2014/10/15)

NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, wherein Z is a group of the formula (i), (ii), (iii), (iv), or (v), and wherein L1, L2, L3, X1, X2, Y, Rz4, Rz5, Rz6, n, R1, R2, R3a, R3b, R4a, R4b, R6a, R6b, R7a, R7b, R11a, R11b, R14, R17, R19, R20, R23a, R23b, and R24 are as defined herein, and pharmaceutical compositions thereof. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of CNS-related conditions in mammals.
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Page/Page column 178; 179; 180

(2013/03/26)

Synthesis and quantitative structure-property relationships of side chain-modified hyodeoxycholic acid derivatives
Bile acids have emerged as versatile signalling compounds of a complex network of nuclear and membrane receptors regulating various endocrine and paracrine functions. The elucidation of the interconnection between the biological pathways under the bile ac
Sabbatini, Paola,Filipponi, Paolo,Sardella, Roccaldo,Natalini, Benedetto,Nuti, Roberto,Macchiarulo, Antonio,Pellicciari, Roberto,Gioiello, Antimo
p. 10497 - 10513
(2013/10/22)

Synthesis of new hyodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave
An efficient and simple method for synthesis of new hyodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave has been developed. Its main advantages are short reaction times, good conversions and the environmentally friendly nature of the process. The preliminary results indicate that some of these compounds possess inhibitory effects against E. coli.
Shi, Zhi Chuan,Zhao, Zhi Gang,Liu, Xing Li,Chen, Yu
experimental part
p. 405 - 408
(2012/01/05)

Corrigendum to "Synthesis and antimicrobial evaluation of bile acid tridentate conjugates" [Steroids 74 (2009) 701-706] (DOI:10.1016/j.steroids.2009.03.005)
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Huang, Liliang,Sun, Yanhong,Zhu, Hua,Zhang, Yuanqing,Xu, Jia,Shen, Yu-Mei
scheme or table
p. 189 - 189
(2010/04/29)

Synthesis and antimicrobial evaluation of bile acid tridentate conjugates
Two series of novel bile acid tridentate conjugates with different linkers were synthesized and characterized, and their biological activities in vitro were evaluated. The procedure was straightforward and efficient to be carried out with high overall yield. The antimicrobial activity of the synthesized compounds against Saccharomyces cerevisiae, Aspergillus niger, Escherichia coli and Staphylococcus aureus was investigated in vitro. The best activity of minimal inhibitory concentrations (MICs) for 1c, 1c′, 2c and 2c′ against S. cerevisiae was up to 0.125 μg/mL.
Huang, Liliang,Sun, Yanhong,Zhu, Hua,Zhang, Yuanqing,Xu, Jia,Shen, Yu-Mei
experimental part
p. 701 - 706
(2009/07/19)

Synthesis and characterization of organometallic rhenium(I{cyrillic, ukrainian}) and technetium(I{cyrillic, ukrainian}) bile acid complexes
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.
Huang, Liliang,Zhu, Hua,Xu, Xiaoping,Zhang, Chunchun,Shen, Yu-Mei
experimental part
p. 3247 - 3253
(2010/01/11)

Methods of treating cancers
This invention relates to methods for treating cancers.
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Page/Page column 6; 11; 12

(2010/11/25)

PURIFICATION PROCESS FOR CHENODEOXYCHOLIC ACID
The present invention relates to a process for purifying chenodeoxycholic acid (3α,7α-dihydroxy-5β-cholic acid). In particular, the present invention relates to a process for purifying chenodeoxycholic acid from low grade of chenodeoxycholic acid mixture in swine bile solid, with high yield and purity.
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Page/Page column 17

(2008/06/13)

A new route for synthesizing cholesterol analogs with fluorocarbon side chains and their liquid-crystalline aliphatic esters
A new and efficient route has been developed to synthesize 17β-(1-methyl-3-perfluoroalkyl)propyl-3β-androsterol (1) in nine steps from hyodeoxycholic acid via selective addition of 1-perfluoroalkyl iodide to 24-norchola-5,22-dien-3β-ol. From (1), the first series of steroidal liquid crystalline aliphatic esters (smectic A) with fluorocarbon side chains has been prepared.
Shen, Yuehai,Wen, Jianxun
p. 13 - 15
(2007/10/03)

The synthesis and characterization of analogs of the antimicrobial compound squalamine: 6β-hydroxy-3-aminosterols synthesized from hyodeoxycholic acid
Analogs of the aminosterol antimicrobial agent squalamine have been synthesized beginning from hyodeoxycholic acid. After carboxylic acid esterification and oxidation of both alcohol functions to ketones, the A/B ring junction was converted from cis to trans by acid-catalyzed isomerization. Different polyamines were added to the 3-keto group by reductive amination, yielding both the 3α and 3β addition products. The synthetic products exhibited potent, broad-spectrum antimicrobial activity similar to that of the parent compound. Changing the identity of the polyamine or the stereochemistry of addition has little effect upon antimicrobial activity but appears to change the selectivity of the agents. The analogs are synthesized with high yield from inexpensive starting materials and are promising alternatives to squalamine as potential antibiotics.
Jones, Stephen R.,Kinney, William A.,Zhang, Xuehai,Jones, Lisa M.,Selinsky, Barry S.
p. 565 - 571
(2007/10/03)

A SIMPLE AND MILD PROCEDURE FOR THE PREPARATION OF BILE ACID METHYL ESTERS.
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Ballini, Roberto,Carotti, Angelo
p. 1197 - 1202
(2007/10/02)

p-Toluenesulfonic acid/methanol: mild reagent for the preparation of bile acid methyl esters.
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.
Dayal,Speck,Bagan,Tint,Salen
p. 239 - 242
(2007/10/02)