石胆酸 | 1053-37-8

• 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
• 中文名称: 石胆酸
• 英文名称: lithocholenic acid
• 英文别名: 3α-hydroxy-5β-chol-11-enoic acid；3α-hydroxy-5β-chol-11-en-24-oic acid；3α-Hydroxy-5β-chol-11-en-24-saeure；3α-Hydroxy-5β-cholen-(11)-saeure-(24)；3α-Hydroxy-5β-chol-11-ensaeure；(4R)-4-[(3R,5R,8S,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 1053-37-8
• 化学式: C₂₄H₃₈O₃
• 分子量: 374.564
• InChiKey: FEGCPHIPSRBREU-HVATVPOCSA-N

物化性质

• 熔点：
  162-163 °C
• 沸点：
  510.8±43.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  石胆酸 在 盐酸 、 氯仿 、 五氯化磷 、 calcium carbonate 作用下， 生成 3β-chloro-5β-chol-11-en-24-oic acid ethyl ester
  参考文献：
  名称：

  Seroflocculating Steroids. I. Ethyl. 3β-Chloro-Δ¹¹-cholenate¹

  摘要：

  DOI：

  10.1021/ja01641a031
• 作为产物：
  描述：

  石胆酸 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以87%的产率得到石胆酸
  参考文献：
  名称：

  The synthesis and antitumor activity of lithocholic acid and its derivatives

  摘要：

  In this paper, a new and concise synthetic route of lithocholic acid (LCA) using commercially available steroid source deoxycholic acid is reported. A series of amide derivatives of LCA were also synthesized and investigated for their activity against the growth of MCF-7 and MCF-7/ADR cells using the sulforhodamine B assay. For MCF-7, the most potent compound 20 showed a 20-fold higher antitumor activity than LCA. For MCF-7/ADR, the most potent compound 24 showed a 22-fold higher antitumor activity than LCA. The transwell migration assay of 20 was evaluated on MDA-MB-231 cells. The colony formation and apoptosis assays of 20 were performed on MCF-7 and MCF-7/ADR cell lines.

  DOI：

  10.1016/j.steroids.2017.06.009

文献信息

• [EN] 3-MODIFIED ISO-/ISOALLO-LITHOCHOLIC ACID DERIVATIVES OR THEIR HOMO-ANALOGS FOR PREVENTING AND TREATING CLOSTRIDIOIDES DIFFICILE-ASSOCIATED DISEASES<br/>[FR] DÉRIVÉS D'ACIDE ISO-/ISOALLO-LITHOCHOLIQUE 3-MODIFIÉS OU LEURS HOMO-ANALOGUES POUR LA PRÉVENTION ET LE TRAITEMENT DE MALADIES ASSOCIÉES À CLOSTRIDIOIDES DIFFICILE
  申请人：PHENEX PHARMACEUTICALS AG

  公开号：WO2020260558A1

  公开（公告）日：2020-12-30

  The present invention relates to isolithocholic acid (3β-hydroxy-5β-cholan-24-oic acid) and isoallolithocholic acid (3β-hydroxy-5α-cholan-24-oic acid) together with the respective 22-homo-analogs or the deuterated analogs, which are modified in 3-position, for preventing or treating Clostridioides difficile-associated disease in a mammalian subject.

  本发明涉及孤立胆烷酸（3β-羟基-5β-胆烷-24-酸）和异孤立胆烷酸（3β-羟基-5α-胆烷-24-酸），以及相应的在3位修饰的22-同系物或氘代同系物，用于预防或治疗哺乳动物主体中的难辨梭菌相关疾病。
• Catalytic Oxidations of Steroid Substrates by Artificial Cytochrome P-450 Enzymes
  作者：Jerry Yang、Bartolo Gabriele、Sandro Belvedere、Ying Huang、Ronald Breslow

  DOI：10.1021/jo020174u

  日期：2002.7.1

  perform hydroxylations with substrate selectivity and regio- and stereoselectivity and high catalytic turnovers. The geometries of the catalyst/substrate complexes override intrinsic substrate reactivities, permitting attack on geometrically accessible saturated carbons of steroids in the presence of secondary carbinol groups and carbon-carbon double bonds, as in enzymatic reactions. Selective hydroxylations

  包含带有环糊精结合基团的锰-卟啉的催化剂能够以底物选择性，区域和立体选择性以及高催化转化率进行羟基化。催化剂/底物配合物的几何形状超越了固有的底物反应性，从而允许在存在仲甲醇基团和碳-碳双键的情况下，如在酶促反应中，攻击类固醇的几何可及的饱和碳。甾族碳9位的选择性羟基化特别实用。
• Ruff et al., Journal of the Chemical Society, 1953, p. 3683,3687
  作者：Ruff et al.

  DOI：——

  日期：——
• The Preparation and Properties of 3(α),11-Dihydroxy-12-ketocholanic Acid
  作者：Bernard B. Longwell、O. Wintersteiner

  DOI：10.1021/ja01858a059

  日期：1940.1
• Turner et al., Journal of Biological Chemistry, 1946, vol. 162, p. 571,573
  作者：Turner et al.

  DOI：——

  日期：——