20231-57-6Relevant academic research and scientific papers
Coordination of sodium cation to an oxygen function and olefinic double bond to form molecular adduct ion in fast atom bombardment mass spectrometry
Morisaki, Naoko,Kobayashi, Hisayoshi,Yamamura, Yumiko,Morisaki, Masuo,Nagasawa, Kazuo,Hashimoto, Yuichi
, p. 935 - 940 (2002)
Steroidal allylic alcohols formed Na+ adduct ion peaks [M+Na]+ by the addition of NaCl in FAB mass spectrometry. A comparison of the intensities of the adduct ion peaks of allylic alcohols with those of the corresponding saturated alcohols and olefin suggested that the olefinic double bond and the proximal hydroxyl group had coordinated to Na +. The adduct ion was stable and did not undergo dehydroxylation. We suggest that the Na+ adduct ion will be useful for the molecular weight determination of allylic alcohols which are susceptible to dehydroxylation under FAB mass spectrometric conditions. Na+ adduct ions of α, β-unsaturated carbonyl compounds were also investigated.
Synthesis of 24-functionalized oxysterols
Khripach,Zhabinskii,Konstantinova,Khripach,Antonchick
, p. 257 - 261 (2002)
The syntheses of (24S)-24,25-epoxycholesterol, (24S)-hydroxycholesterol, and 24-ketocholesterol are described. The compounds belong to oxysterols, which can be considered to be the modulators of cholesterol metabolism. The asymmetric hydroxylation of desmosterol acetate according to Sharpless was used as the key reaction in the stereoselective introduction of functionality in position 24.
Elucidation of Distinct Modular Assemblies of Smoothened Receptor by Bitopic Ligand Measurement
Zhao, Fei,Wu, Yiran,Zhou, Fang,Xue, Dongxiang,Zhao, Simeng,Lu, Wanglong,Liu, Xiaoyan,Hu, Tao,Qiu, Yanli,Li, Rongyan,Gu, Tangjie,Xu, Yueming,Xu, Fei,Zhong, Guisheng,Jiang, Zhongxing,Zhao, Suwen,Tao, Houchao
supporting information, p. 13830 - 13840 (2021/09/28)
Class F G protein-coupled receptors are characterized by a large extracellular domain (ECD) in addition to the common transmembrane domain (TMD) with seven α-helixes. For smoothened receptor (SMO), structural studies revealed dissected ECD and TMD, and th
Synthesis method of saringosterol
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, (2022/01/10)
The invention discloses a synthesis method of saringosterol. The synthesis method comprises the following steps of: carrying out esterification on hyodeoxycholic acid serving as a raw material to generate hyodeoxycholate or directly carrying out sulfonylation reaction on the hyodeoxycholate serving as a raw material to generate 3, 6-disulfonyl hyodeoxycholate, then carrying out nucleophilic substitution-elimination reaction to generate 3beta-hydroxychol-5-ene-24-acid ester, then performing reaction with N, O-dimethyl hydroxylamine to prepare weinreb amide, and carrying out two-step Green Nisi reaction to finally obtain sargassterol. The synthesis method disclosed by the invention is mild in reaction condition, relatively short in reaction time, low in price of the starting raw material hyodeoxycholic acid and the reaction reagent, relatively high in final yield and suitable for large-scale preparation of the sargassterol.
An effective synthesis of ursodeoxycholic acid from dehydroepiandrosterone
Chen, Wang,Hu, Daihua,Feng, Zili,Liu, Zhaopeng
supporting information, (2021/06/16)
A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from plant-source dehydroepiandrosterone (DHEA), with a Mistunobu reaction and regioselective allyl oxidationat as the key steps. The reaction conditions of the key allyl oxidation reaction were also investigated and optimized, including solvent, oxidant and reaction temperature. In this novel route for the preparation of UDCA, most of the reaction steps have high conversions and overall yield up to 35% for 8 steps. Since all starting materials are cost-effective, commercially available and effectively avoided the risk of animal derived raw materials, this promising synthetic route offers economical and efficient strategies for potential production of UDCA.
A concise synthesis of 25-Hydroxycholesterol from hyodesoxycholic Acid
Jin, Can,Wang, Yulei,Sun, Bin,Su, Weike
, p. 96 - 99 (2018/03/21)
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.
OXYSTEROLS AND METHODS OF USE THEREOF
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Paragraph 00750, (2018/05/16)
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.
Cholesterol molecular probe as well as preparation method and application thereof
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Paragraph 0117; 0118, (2017/07/21)
The invention discloses a cholesterol molecular probe and a preparation method thereof. The cholesterol molecular probe shown as a formula (I) is prepared by taking lithocholic acid as a raw material through esterification reaction, oxidization reaction, dehydrogenation reaction, carbonyl protection reaction, reduction reaction, hydroxyl protection reaction, reduction reaction, iodination reaction, substitution reaction and de-protection reaction. The invention further discloses application of the cholesterol molecular probe shown as the formula (I) to identification of cholesterol modified protein. The cholesterol molecular probe provided by the invention can be used for simulating normal cholesterol to promote cell growth, and prompting the shearing ripening of the cholesterol modified protein hedgehog, and can also be used for researching cholesterol modification of the protein.
Novel 3,4-seco bile acid diamides as selective anticancer proliferation and migration agents
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)
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.
Design and synthesis of a crosslinker for studying intracellular steroid trafficking pathways
Byrd, Katherine M.,Arieno, Marcus D.,Kennelly, Megan E.,Estiu, Guillermina,Wiest, Olaf,Helquist, Paul
, p. 3843 - 3851 (2015/07/27)
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
