20(17->12β)-abeo-des-A,B-24-trihomo-21-norcholestan-8β,25-diol | 881182-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 20(17->12β)-abeo-des-A,B-24-trihomo-21-norcholestan-8β,25-diol
• 英文别名: (3aR,4S,7R,7aS)-7-(8-hydroxy-8-methylnonyl)-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-ol
• CAS: 881182-58-7
• 化学式: C₂₀H₃₈O₂
• 分子量: 310.521
• InChiKey: OARNMTFIVYSXTR-LXZJYRNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  20(17->12β)-abeo-des-A,B-24-trihomo-21-norcholestan-8β,25-diol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以95%的产率得到20(17->12β)-abeo-25-hydroxy-des-A,B-24-trihomo-21-norcholestan-8-one
  参考文献：
  名称：

  Novel 1α,25-Dihydroxyvitamin D₃ Analogues with the Side Chain at C12

  摘要：

  The plethora of actions of 1 alpha,25(OH)(2)D-3 in various systems suggested wide clinical applications of vitamin D nuclear receptor (VDR) ligands in treatments of inflammation, dermatological indication, osteoporosis, cancers, and autoimmune diseases. More than 3000 vitamin D analogues have been synthesized in order to reduce the calcemic side effects while maintaining the transactivation potency of the natural ligand. In light of the crystal structures of the vitamin D nuclear receptor (VDR), novel analogues of the hormone 1 alpha,25(OH)2D3 with side chains attached to C-12 were synthesized via the convergent Wittig-Horner approach. Among the compounds studied, the analogue 2b showed the highest binding affinity for VDR and was the most potent at inducing VDR transcriptional activity in a transient transfection assay (20% of the transactivation activity of the natural ligand).

  DOI：

  10.1021/jm049016g
• 作为产物：
  描述：

  2-methyl-3-nonyn-2-ol 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 氢气 、 potassium hydride 、 1,3-丙二胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 二乙胺 为溶剂， 反应 86.0h， 生成 20(17->12β)-abeo-des-A,B-24-trihomo-21-norcholestan-8β,25-diol
  参考文献：
  名称：

  Novel 1α,25-Dihydroxyvitamin D₃ Analogues with the Side Chain at C12

  摘要：

  The plethora of actions of 1 alpha,25(OH)(2)D-3 in various systems suggested wide clinical applications of vitamin D nuclear receptor (VDR) ligands in treatments of inflammation, dermatological indication, osteoporosis, cancers, and autoimmune diseases. More than 3000 vitamin D analogues have been synthesized in order to reduce the calcemic side effects while maintaining the transactivation potency of the natural ligand. In light of the crystal structures of the vitamin D nuclear receptor (VDR), novel analogues of the hormone 1 alpha,25(OH)2D3 with side chains attached to C-12 were synthesized via the convergent Wittig-Horner approach. Among the compounds studied, the analogue 2b showed the highest binding affinity for VDR and was the most potent at inducing VDR transcriptional activity in a transient transfection assay (20% of the transactivation activity of the natural ligand).

  DOI：

  10.1021/jm049016g