8β-tert-butyldimethylsilyloxy-des-A,B-androstan-12-one | 881182-35-0

• 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: 8β-tert-butyldimethylsilyloxy-des-A,B-androstan-12-one
• 英文别名: (3aR,7S,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-3a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-4-one
• CAS: 881182-35-0
• 化学式: C₁₆H₃₀O₂Si
• 分子量: 282.498
• InChiKey: QEDRMCCBMBRUBB-HEHGZKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8β-tert-butyldimethylsilyloxy-des-A,B-androstan-12-one 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 重铬酸吡啶 、 正丁基锂 、 四丁基氟化铵 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 二乙胺 为溶剂， 反应 151.0h， 生成 20(17->12β)-abeo-1α,25-dihydroxy-24-homo-21-norvitamin D₃
  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：

  8β-tert-butyldimethylsilyloxy-des-A,B-androst-9(11)-en 在 palladium on activated charcoal 六甲基磷酰三胺 、 重铬酸吡啶 、 lithium diethylamide 、 氢气 、 sodium naphthalenide 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 59.33h， 生成 8β-tert-butyldimethylsilyloxy-des-A,B-androstan-12-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

文献信息

• Novel 1α,25-Dihydroxyvitamin D₃ Analogues with the Side Chain at C12
  作者：Xosé C. González-Avión、Antonio Mouriño、Natacha Rochel、Dino Moras

  DOI：10.1021/jm049016g

  日期：2006.3.1

  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).