24-nor-5β-cholane-3α,12α,23-triol | 68896-33-3

• 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: 24-nor-5β-cholane-3α,12α,23-triol
• 英文别名: 24-nor-5β-cholanetriol-(3α.12α.23)；(10S)-3t.12t-Dihydroxy-10r.13c-dimethyl-17c-((R)-3-hydroxy-1-methyl-propyl)-(5cH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3α.12α-Dihydroxy-10.13-dimethyl-17β-((R)-3-hydroxy-1-methyl-propyl)-5β-gonan；24-Nor-5β-cholantriol-(3α.12α.23)；24-Nor-5beta-cholane-3alpha,12alpha,23-triol；(3R,5R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-4-hydroxybutan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
• CAS: 68896-33-3
• 化学式: C₂₃H₄₀O₃
• 分子量: 364.569
• InChiKey: JWKNPWJGFZVWMB-XQNRYLPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  24-nor-5β-cholane-3α,12α,23-triol 在 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 23-iodo-24-nor-5β-cholane-3α,12α-diol
  参考文献：
  名称：

  Synthesis of sulfonate analogs of bile acids

  摘要：

  Sulfonate analogs of C23 and C24 bile acids were synthesized from norcholic, norchenodeoxycholic, norursodeoxycholic, nordeoxycholic, norhyodeoxycholic, cholic, deoxycholic, hyodeoxycholic, and lithocholic acids. The principal reactions used were (1) reduction of the bile acids with NaBH4 to the corresponding bile alcohols, (2) selective tosylation of the terminal hydroxyl group, (3) iodination of the tosyl esters with NaI, and (4) treatment of the iodides with Na2SO3 to form the sulfonate analogs of the bile acids. The sulfonate analogs showed polarity similar to that of taurine-conjugated bile acids on thin-layer chromatography. The carbon 13 nuclear magnetic resonance spectral data for the sulfonate analogs were tabulated.

  DOI：

  10.1016/0039-128x(92)90008-w
• 作为产物：
  描述：

  去甲脱氧氯酸 在 sodium tetrahydroborate 、 氯甲酸乙酯 、 三乙胺 作用下， 生成 24-nor-5β-cholane-3α,12α,23-triol
  参考文献：
  名称：

  Synthesis of sulfonate analogs of bile acids

  摘要：

  Sulfonate analogs of C23 and C24 bile acids were synthesized from norcholic, norchenodeoxycholic, norursodeoxycholic, nordeoxycholic, norhyodeoxycholic, cholic, deoxycholic, hyodeoxycholic, and lithocholic acids. The principal reactions used were (1) reduction of the bile acids with NaBH4 to the corresponding bile alcohols, (2) selective tosylation of the terminal hydroxyl group, (3) iodination of the tosyl esters with NaI, and (4) treatment of the iodides with Na2SO3 to form the sulfonate analogs of the bile acids. The sulfonate analogs showed polarity similar to that of taurine-conjugated bile acids on thin-layer chromatography. The carbon 13 nuclear magnetic resonance spectral data for the sulfonate analogs were tabulated.

  DOI：

  10.1016/0039-128x(92)90008-w

文献信息

• Steroid Acids and their Transformation Products. VI. Some New Aldehydes and Their Derived Cyanohydrins
  作者：A. Vern. McIntosh、Anna Mae. Searcy、Elizabeth M. Meinzer、Robert H. Levin

  DOI：10.1021/ja01178a013

  日期：1949.10
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.
• Synthesis of sulfonate analogs of bile acids
  作者：Kihira Kenji、Mikami Takahiro、Ikawa Seiichiro、Okamoto Akira、Yoshii Michiko、Miki Shigeo、Erwin H. Mosbach、Hoshita Takahiko

  DOI：10.1016/0039-128x(92)90008-w

  日期：1992.4

  Sulfonate analogs of C23 and C24 bile acids were synthesized from norcholic, norchenodeoxycholic, norursodeoxycholic, nordeoxycholic, norhyodeoxycholic, cholic, deoxycholic, hyodeoxycholic, and lithocholic acids. The principal reactions used were (1) reduction of the bile acids with NaBH4 to the corresponding bile alcohols, (2) selective tosylation of the terminal hydroxyl group, (3) iodination of the tosyl esters with NaI, and (4) treatment of the iodides with Na2SO3 to form the sulfonate analogs of the bile acids. The sulfonate analogs showed polarity similar to that of taurine-conjugated bile acids on thin-layer chromatography. The carbon 13 nuclear magnetic resonance spectral data for the sulfonate analogs were tabulated.