11β-allenyl-3,3-ethylenethioxy-19-nor-17α-pregna-4,9-diene-21,17-carbolactone | 138306-86-2

• 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: 11β-allenyl-3,3-ethylenethioxy-19-nor-17α-pregna-4,9-diene-21,17-carbolactone
• CAS: 138306-86-2
• 化学式: C₂₆H₃₂O₂S₂
• 分子量: 440.671
• InChiKey: DVHXOMUMTFRHGR-LZDJTLFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11β-allenyl-3,3-ethylenethioxy-19-nor-17α-pregna-4,9-diene-21,17-carbolactone 在 N-氯代丁二酰亚胺 、 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 11β-allenyl-3-oxo-19-nor-17α-pregna-4,9-diene-21,17-carbolactone
  参考文献：
  名称：

  Synthesis of new 11.beta.-substituted spirolactone derivatives. Relationship with affinity for mineralocorticoid and glucocorticoid receptors

  摘要：

  Various steroidal 17-spirolactones substituted in the 11beta-position were synthesized to study the relationship between the nature of the 11beta-arm and their affinity for cytosolic mineralocorticoid (MR) and glucocorticoid (GR) receptors prepared from adrenalectomized rabbit kidney or liver. One of them, the 11beta-allenyl-3-oxo-19-nor-17-pregna-4,9-diene-21,17-carbolactone derivative, exhibited the same affinity for MR as aldosterone and a 5-fold higher affinity than mespirenone. Its affinity for GR was found to be relatively low. As suggested by molecular modeling, the marked differences in mineralocorticoid receptor binding affinity could be related to the structural features induced by this 11beta-allenic substituent.

  DOI：

  10.1021/jm00068a018
• 作为产物：
  描述：

  在 盐酸 、 氢氧化钾 、 trimethylsulfonium iodide 、 sodium hydride 、 lithium diisopropyl amide 作用下， 生成 11β-allenyl-3,3-ethylenethioxy-19-nor-17α-pregna-4,9-diene-21,17-carbolactone
  参考文献：
  名称：

  Synthesis of new 11.beta.-substituted spirolactone derivatives. Relationship with affinity for mineralocorticoid and glucocorticoid receptors

  摘要：

  Various steroidal 17-spirolactones substituted in the 11beta-position were synthesized to study the relationship between the nature of the 11beta-arm and their affinity for cytosolic mineralocorticoid (MR) and glucocorticoid (GR) receptors prepared from adrenalectomized rabbit kidney or liver. One of them, the 11beta-allenyl-3-oxo-19-nor-17-pregna-4,9-diene-21,17-carbolactone derivative, exhibited the same affinity for MR as aldosterone and a 5-fold higher affinity than mespirenone. Its affinity for GR was found to be relatively low. As suggested by molecular modeling, the marked differences in mineralocorticoid receptor binding affinity could be related to the structural features induced by this 11beta-allenic substituent.

  DOI：

  10.1021/jm00068a018

文献信息

• Synthesis of new 11.beta.-substituted spirolactone derivatives. Relationship with affinity for mineralocorticoid and glucocorticoid receptors
  作者：Michel Claire、Hassane Faraj、Gerard Grassy、Andre Aumelas、Anne Rondot、Gilles Auzou

  DOI：10.1021/jm00068a018

  日期：1993.8

  Various steroidal 17-spirolactones substituted in the 11beta-position were synthesized to study the relationship between the nature of the 11beta-arm and their affinity for cytosolic mineralocorticoid (MR) and glucocorticoid (GR) receptors prepared from adrenalectomized rabbit kidney or liver. One of them, the 11beta-allenyl-3-oxo-19-nor-17-pregna-4,9-diene-21,17-carbolactone derivative, exhibited the same affinity for MR as aldosterone and a 5-fold higher affinity than mespirenone. Its affinity for GR was found to be relatively low. As suggested by molecular modeling, the marked differences in mineralocorticoid receptor binding affinity could be related to the structural features induced by this 11beta-allenic substituent.