(17->12β)-abeo-8β-tert-butyldimethylsilyloxy-des-A,B-24-dihomo-21-norcholestan-25-ol | 881182-54-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (17->12β)-abeo-8β-tert-butyldimethylsilyloxy-des-A,B-24-dihomo-21-norcholestan-25-ol
• 英文别名: 8-[(3aS,4R,7S,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-3a-methyl-1,2,3,4,5,6,7,7a-octahydroinden-4-yl]-2-methyloctan-2-ol
• CAS: 881182-54-3
• 化学式: C₂₅H₅₀O₂Si
• 分子量: 410.756
• InChiKey: BZRCTRPBBMQNIL-KXEAFHOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (17->12β)-abeo-8β-tert-butyldimethylsilyloxy-des-A,B-24-dihomo-21-norcholestan-25-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以94%的产率得到20(17->12β)-abeo-des-A,B-24-dihomo-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
• 作为产物：
  描述：

  2-methyl-3-octyn-2-ol 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 potassium hydride 、 1,3-丙二胺 作用下， 以 乙酸乙酯 、 二乙胺 为溶剂， 反应 38.0h， 生成 (17->12β)-abeo-8β-tert-butyldimethylsilyloxy-des-A,B-24-dihomo-21-norcholestan-25-ol
  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