8β-tert-butyldimethylsilyloxy-des-A,B-androst-11-en-12-yl-trifluoromethanesulfonate | 881182-46-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 8β-tert-butyldimethylsilyloxy-des-A,B-androst-11-en-12-yl-trifluoromethanesulfonate
• 英文别名: [(3aR,7S,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-3a-methyl-1,2,3,6,7,7a-hexahydroinden-4-yl] trifluoromethanesulfonate
• CAS: 881182-46-3
• 化学式: C₁₇H₂₉F₃O₄SSi
• 分子量: 414.562
• InChiKey: DVFJPXZLYNOMOT-HEHGZKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8β-tert-butyldimethylsilyloxy-des-A,B-androst-11-en-12-yl-trifluoromethanesulfonate 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 重铬酸吡啶 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 二乙胺 为溶剂， 反应 71.0h， 生成 20(17->12β)-abeo-25-hydroxy-des-A,B-24-homo-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：

  8β-tert-butyldimethylsilyloxy-des-A,B-androst-11-en-9α-ol 在 palladium on activated charcoal 重铬酸吡啶 、 氢气 、 sodium naphthalenide 、 三乙胺 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 93.33h， 生成 8β-tert-butyldimethylsilyloxy-des-A,B-androst-11-en-12-yl-trifluoromethanesulfonate
  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).