CAS: 20380-11-4; (25R)-Cholest-5-Ene-3β,26-Diol

该化合物是一种氧气激素和胆固醇的代谢物,由CYP27A1的酶氧化形成. 它在脂质新陈代谢中起着重要作用,作为肝X受体(LXRs)和雌激素受体的内生离子离子体,从而影响胆固醇的回旋,炎症和免疫反应.由于对细胞路径的调控作用,这种分子对与脉冲硬化,...

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上下游产品

(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-羟基-6-甲基庚烷-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇 26-Hydroxycholesterol 13095-61-9
24-Norchol-5-En-3β,23-Diol 64907-38-6
胆固醇 Cholesterol 57-88-5
3Beta-Hydroxycholest-5-En-26-Al 32557-11-2
27-去甲-25-氧代胆固醇 27-Nor-5-Cholesten-3β-Ol-25-One 7494-34-0
(25R)-Cholest-5-En-3β,16β,26-Triol 31327-56-7
(25R)-26-Acetoxycholest-5-En-3β-Ol 192187-72-7
孕烯醇酮 Pregnenolone 145-13-1 (25R)-26-Hydroxy-16-Oxocholesterol 77611-30-4 Kryptogenin 468-99-5

合成工艺路线路线简述

    📜薯蓣皂素置于吡啶,盐酸,Lithium Aluminium Tetrahydride,锌体系中,用 四氢呋喃,乙醚,乙醇,水 用作溶剂,化学反应 11.5H,反应生成5,25R-胆甾烯-3Beta,26-二醇
    参考文献:Semi-Synthesis And Biological Evaluation Of 25(R)-26-Acetoxy-3β,5α-Dihydroxycholest-6-One
    标题:Semi-Synthesis And Biological Evaluation Of 25(R)-26-Acetoxy-3β,5α-Dihydroxycholest-6-One
    摘要:此前,我们发现了一系列类固醇(1-6),它们对呼吸道合胞病毒(rsv)具有很强的抗病毒活性,Ic50值从3.23到0.19 µm不等.在这项工作中,我们首先从市售化合物 Diosgenin(7)出发,通过七个步骤半合成并表征了 5,25(R)-26-乙酰氧基-3β,5α-二羟基胆甾烷-6-酮的单一异构体,命名为 (25R)-5,总产率为 2.8%.遗憾的是,化合物 (25R)-5 及其中间体在 10 µm 浓度下对 Rsv 的复制只有轻微的抑制作用,但它们对人膀胱癌 5637(htb-9)和肝癌 Hepg2 具有很强的细胞毒性活性,Ic50 值从 3.0 µm 到 15.5 µm 不等,在 20 µm 浓度下对正常肝细胞的增殖没有任何影响.其中,目标化合物(25R)-5 对 5637(htb-9)和 Hepg2 具有细胞毒性活性,Ic50 值分别为 4.8 µm 和 15.5 µm.进一步研究表明,化合物 (25R)-5 可通过诱导早期和晚期细胞凋亡抑制癌细胞增殖.总之,我们对化合物 5 的 25R 异构体进行了半合成,表征和生物学评价;生物学结果表明,化合物 (25R)-5 可能是进一步抗癌研究,尤其是抗人类肝癌研究的非常好先导.
    Doi:10.3390/md21030191

    海关参考信息

    专利信息


    专利号:US-2025305010-A1
    优先权日:2022-05-08
    标题:Lipid compositions and methods of producing same
    发明人:KEREN TOMER; ELLA EZRA; ARGOV-ARGAMAN NURIT
    权利人:WILK TECH INTERNATIONAL LTD; YISSUM RES DEV CO OF HEBREW UNIV JERUSALEM LTD
    摘要:Provided is a method of increasing lipid synthesis or accumulation in mammary epithelial cells (MECs) culture and optionally secretion therefrom. The method comprising contacting the MECs with an LXR agonist in the presence of a fatty acid to thereby increase lipid synthesis or accumulation and optionally secretion of lipids. Also provided is a method of producing synthetic fat globules, the method comprising: (a) isolating lipid droplets from cells in culture; (b) encapsulating the droplets with a lipid bilayer, thereby producing synthetic fat globules. Also provided are compositions produced thereby.

    专利号:US-7339065-B2
    优先权日:2003-07-21
    标题 :Design and synthesis of optimized ligands for PPAR
    发明人:AVERY MITCHELL A; PERSHADSINGH HARRIHAR A
    权利人:BETHESDA PHARMACEUTICALS INC; UNIV MISSISSIPPI
    摘要:This invention provides new chemical entities useful for treating a variety of clinical disorders including those that are influenced by the activity of peroxisome proliferator activated receptors (PPAR). The structures of the compounds and methods to design, make and use the compounds are provided. Compounds and methods for administering therapeutic compositions comprising the compounds in cases of the disease psoriasis are provided. An exemplary compound having the formula compound is 5adamantan-2-yl-pentanoic acid {2-[4-(2,4-dioxo-thiazolidin-5-yl-methyl)-phenoxy]-ethyl}-methyl-amide is provided.

    专利号:US-2018148745-A1
    优先权日:2015-05-26
    标题:Hemoprotein catalysts for improved enantioselective enzymatic synthesis of ticagrelor
    发明人:ARNOLD FRANCIS H; RENATA HANS; MCINTOSH JOHN A; LEWIS RUSSELL D; KAN SEK BIK JENNIFER; HERNANDEZ KARI; COELHO PEDRO; ROZZELL DAVID; ZHANG CHEN
    权利人:CALIFORNIA INST OF TECHN; PROVIVI INC
    摘要:The present invention provides methods by which trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine and related cyclopropane compounds are prepared using synthetic strategies that include a biocatalytic cyclopropanation step.

    专利号:WO-2011107023-A1
    优先权日:2010-03-05
    标题:Compounds for preventing and treating disorders of metabolism and uses thereof
    发明人:SONG BAOLIANG; TANG JINGJIE; LI JIAGUI; LI PEISHAN; QI WEI
    权利人:SHANGHAI INST BIOL SCIENCES; SONG BAOLIANG; TANG JINGJIE; LI JIAGUI; LI PEISHAN; QI WEI
    摘要:The present invention provides compounds and uses thereof for preventing and treating metabolic disorders such as hyperlipemia, atherosclerosis, type II diabetes and so on. The present invention firstly discloses new inhibitors by SREBP route which can specifically inhibit the synthesis of lipid such as cholesterol, fatty acid, triglyceride and so on by inhibiting the SREBP route and can reduce the level of lipid. So the present invention can provide a new method for preventing and treating metabolic disorders such as adiposity, atherosclerosis, type II diabetes and so on.

    专利号:US-9650407-B2
    优先权日:2011-11-02
    标 题 :Reprogramming of cellular adhesion
    发明人:GARTNER ZEV JORDAN; SELDEN NICHOLAS SCOTT; TODHUNTER MICHAEL E; LIANG SAMANTHA ISABEL; WEBER ROBERT JOSEPH; JEE NOEL YOUNGHO; LIU JENNIFER S
    权利人:UNIV CALIFORNIA
    摘要:Disclosed are membrane-anchored polynucleotides, and compositions comprising the membrane-anchored polynucleotides. Also disclosed are the processes for the synthesis of these compounds, compositions comprising such compounds, and the use of such compounds and compositions in research and therapeutic applications.

    专利号:WO-9947136-A1
    优先权日:1998-03-19
    标题 :Prevention and treatment of adhesions
    发明人:KOOISTRA TEAKE; GOEDDE MARTIN FRANZ
    权利人:TNO; KOOISTRA TEAKE; GOEDDE MARTIN FRANZ
    摘要:The invention relates to medical treatments and compositions to prevent or reduce the occurrence of adhesions to and between body organs, parts of body organs and/or tissues in animals, in particular human beings, such as the adhesions occurring after surgical proccedures. The invention provides for reducing or preventing adhesions to or between organs, parts of organs or tissues, at a particular location, in an animal, comprising subjecting said animal to a treatment which provides for increased synthesis and/or secretion of plasminogen activator by mesothelial cells present at said location, or to a treatment which provides for decreased synthesis and/or secretion of plasminogen activator inhibitor by mesothelial cells present at said location. The active agents are selelcted form the group composed of vastatins or distinct natural oxysterols, such as 22 (R)-hydroxycholesterol, mevalonate, or geranylgeraniol or combinations thereof, optionally combined with retinoic acid.

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    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Hashimoto Y, Sugiura H, Togo S, Koarai A, Abe K, Yamada M, Ichikawa T, Kikuchi T, Numakura T, Onodera K, Tanaka R, Sato K, Yanagisawa S, Okazaki T, Tamada T, Kikuchi T, Hoshikawa Y, Okada Y, Ichinose M. 27-Hydroxycholesterol accelerates cellular senescence in human lung resident cells. Am J Physiol Lung Cell Mol Physiol. 2016 Jun 1;310(11):L1028-41. doi: 10.1152/ajplung.00351.2015. Epub 2016 Apr 1. doi: 10.3233/JAD-150734. doi: 10.1002/iub.1465. Epub 2016 Jan 12. doi: 10.1007/s12032-015-0725-5. Epub 2016 Jan 5. doi: 10.1016/j.freeradbiomed.2015.12.007. Epub 2015 Dec 10. doi: 10.1002/biof.1243. Epub 2015 Dec 16. doi: 10.1007/978-1-4939-3127-9_34. doi: 10.1007/s11010-015-2551-7. Epub 2015 Sep 8.
    12: Zhang DD, Yu HL, Ma WW, Liu QR, Han J, Wang H, Xiao R. 27-Hydroxycholesterol contributes to disruptive effects on learning and memory by modulating cholesterol metabolism in the rat brain. Neuroscience. 2015 Aug 6;300:163-73. doi: 10.1016/j.neuroscience.2015.05.022. Epub 2015 May 16. doi: 10.1111/acel.12322. Epub 2015 Mar 10.
    14: Lee WR, Ishikawa T, Umetani M. The interaction between metabolism, cancer and cardiovascular disease, connected by 27-hydroxycholesterol. Clin Lipidol. 2014;9(6):617-624.

    合成参考文献


    参考文献:10.3233/jad-2010-1298
    摘要:Marwarha G, Dasari B, Prasanthi JRP, Schommer J, Ghribi O. RETRACTED: Leptin Reduces the Accumulation of Aβ and Phosphorylated Tau Induced by 27-Hydroxycholesterol in Rabbit Organotypic Slices. Journal of Alzheimer’s Disease. 2010 Jan 28;19(3):1007–19. doi: 10.3233/jad-2010-1298.
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