ethoxycarbonyl (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate | 196505-69-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: ethoxycarbonyl (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 196505-69-8
• 化学式: C₂₇H₄₄O₆
• 分子量: 464.643
• InChiKey: KXJQIYYPYGGBPB-MKQJCDGFSA-N

物化性质

• 沸点：
  562.0±56.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethoxycarbonyl (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate 在 tetrachloropyrophosphate 作用下， 以 1,4-二氧六环 、 sodium hydroxide 、 氯仿 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Basic Studies on 5-(7-Hydroxy-3-Ophosphonocholyl)aminosalicylic Acid for the Evaluation of Microbial Overgrowth.

  摘要：

  一种新合成的7-羟基-3-O-膦酸胆酸（熊去氧胆酸单膦酸盐）与5-氨基水杨酸（5-ASA-UDCA单膦酸盐）的结合物被研究，以确定其是否适合用于评估肠道细菌。这种化合物，5-ASA-UDCA单膦酸盐，能被胆酰甘氨酸水解酶高效去结合释放5-ASA，而对胰腺和肠粘膜酶的去结合完全不敏感。在翻转肠囊实验中，5-ASA-UDCA单膦酸盐在小肠的任何部分都没有主动吸收。在动物实验中，口服20 mg的5-ASA-UDCA单膦酸盐后，测量了24小时的N-乙酰-5-ASA（Ac-5ASA）尿排泄量。对照组大鼠排泄了276.3±89.0 μg（均值±标准误）的Ac-5ASA，而肠道细菌过度生长的大鼠排泄更多（1224.1±231.5 μg；p<0.01）。这些基础研究表明，这种化合物可能提供一种简单的方法来评估微生物过度生长，无需使用放射性同位素或昂贵、特殊的设备。

  DOI：

  10.1248/bpb.20.370
• 作为产物：
  描述：

  acid bile salt 生成 ethoxycarbonyl (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
  参考文献：
  名称：

  牛磺熊去氧胆酸钠的制备方法

  摘要：

  本发明提出了一种牛磺熊去氧胆酸钠的制备方法，包括：(1)以熊去氧胆酸为原料，经过乙酰化、酰氯化反应得到混合酸酐溶液；(2)将牛磺酸溶于碳酸钠溶液中，得到牛磺酸的碳酸钠溶液；将所述牛磺酸的碳酸钠溶液滴加到步骤(1)中的混合酸酐溶液中，搅拌，滤除沉淀得滤液；(3)将步骤(2)中的滤液的pH调整为6～7，浓缩干燥得牛磺熊去氧胆酸粗品干燥物；(4)将步骤(3)中的浓缩干燥物脱盐纯化和重结晶，即得牛磺熊去氧胆酸。本发明成本低，工艺路线短，得率高达78％，适于工业化规模生产。

  公开号：

  CN102718829B

文献信息

• Process for the preparation of tauroursodesoxycholic acid
  申请人：PRODOTTI CHIMICI E ALIMENTARI SPA

  公开号：EP1985622A1

  公开（公告）日：2008-10-29

  The present invention relates to a novel method for preparing tauroursodeoxycholic acid which comprises a step of selective precipitation of the impurities present in the suspension obtained from the reaction of an aqueous solution of sodium taurinate with an acetonic solution of a mixed anhydride of ursodeoxycholic acid with an alkyl chloroformate.

  本发明涉及一种制备牛磺胆酸的新方法，包括通过选择性沉淀来去除从水溶性牛磺酸钠与乙酮溶液中的醇氧化胆酸混合酐的烷基氯甲酸酯反应产生的悬浮液中存在的杂质的步骤。
• Bile acid–cysteamine conjugates: Structural properties, gelation, and toxicity evaluation
  作者：Virpi Noponen、Heini Belt、Manu Lahtinen、Arto Valkonen、Hannu Salo、Jitka Ulrichová、Adéla Galandáková、Elina Sievänen

  DOI：10.1016/j.steroids.2011.11.006

  日期：2012.2

  Design, synthesis, and characterization of six novel bile acid-cysteamine conjugates together with investigation of their structural studies, gelation properties, and preliminary toxicity evaluation, are reported. Solid state properties of selected compounds were studied by means of X-ray diffraction and C-13 CPMAS NMR spectroscopy. N-(2-thioethyl)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholan-24-amide was shown to exhibit (pseudo)polymorphism, and a single crystal structure of its non-stoichiometric hydrate is reported herein. Cholyl and dehydrocholyl derivatives bearing three functionalities in their steroidal backbone were shown to undergo self-assembly leading to gelation in certain organic solvents. Preliminary morphology studies of the formed gels by scanning electron microscopy (SEM) were performed. The standard model mouse fibroblast cell line together with the MTT and NR tests were utilized for evaluating the toxicity of the prepared compounds. Lithocholyl, ursodeoxycholyl, and dehydrocholyl derivatives turned out to be relatively non-toxic in the conditions studied. (C) 2011 Elsevier Inc. All rights reserved.
• Synthesis and Physicochemical, Biological, and Pharmacological Properties of New Bile Acids Amidated with Cyclic Amino Acids
  作者：Aldo Roda、Carolina Cerrè、Anna C. Manetta、Gianfranco Cainelli、Achille Umani-Ronchi、Mauro Panunzio

  DOI：10.1021/jm9508503

  日期：1996.1.1

  New analogs of cyclic amino acid-conjugated bile acids were synthesized, and their physicochemical and biological properties were compared with those of natural analogs. Ursodeoxycholic acid was amidated with D-proline, L-proline, 4-hydroxy-L-proline, and 4-methoxy-L-proline. Hyocholic and hyodeoxycholic acids were amidated with L-proline. The physicochemical properties were similar to those of the natural analogs. All of them were highly stable toward enzymatic C-24 amide bond hydrolysis and 7-dehydroxylation. Their transport, metabolism, and effect on biliary lipid secretion were evaluated in bile fistula rat after intravenous infusion. All the analogs were secreted in bile unmodified. The 4-methoxy-L-proline derivative produced the highest secretion rate, much higher than those of all the other natural and synthetic analogs. This was associated with a selective reduction of cholesterol secretion with normal phospholipid secretion and choleresis. When coinfused, all the analogs were able to prevent the hepatotoxicity induced by intravenous taurochenodeoxycholic acid, as revealed by normal choleresis, alkaline phosphatase, and lactate dehydrogenase values in bile. Considering the overall data, 4-methoxy-L-proline, 4-hydroxy-L-proline, and L-proline derivatives of ursodeoxycholic acid were more potent than the natural analogs.