1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-(2-oxopropoxy)pregna-5,7,16-triene | 881382-07-6

• 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: 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-(2-oxopropoxy)pregna-5,7,16-triene
• CAS: 881382-07-6
• 化学式: C₃₆H₆₂O₄Si₂
• 分子量: 615.057
• InChiKey: YWFQJGQKVFGCGH-LWDSCMKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.79
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-(2-oxopropoxy)pregna-5,7,16-triene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.25h， 生成 1α,3β-dihydroxy-20(S)-(2-hydroxy-2-methylpropoxy)pregna-5,7,16-triene
  参考文献：
  名称：

  Novel vitamin D3 antipsoriatic antedrugs: 16-En-22-oxa-1α,25-(OH)2D3 analogs

  摘要：

  A series of 16-en-22-oxa-derivatives of vitamin D-3 based on the structure of maxacalcitol (2) were prepared. Maxacalcitol is currently used topically for the treatment of psoriasis and is recognized as the most successful antedrug of natural vitamin D-3 because it retains the original antiproliferative activity of calcitriol without increased calcemic activity. We introduced 16-olefinic functionality to accelerate the oxidative metabolism of the drug in liver, presumed to be essential for the reduction of calcemic activity, and modified the side-chain moiety by placing the 22-oxygen on the more labile allylic carbon center. Novel 22-oxa analogs (7a-i), carrying either the 24-alkynyl bond or 24-hydroxy functionality in addition to the 16-double bond were synthesized and their pharmacokinetics were evaluated. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.034
• 作为产物：
  描述：

  1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-(2,3(R)-epoxypropoxy)pregna-5,7,16-triene 在 lithium aluminium tetrahydride 、 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.92h， 生成 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-(2-oxopropoxy)pregna-5,7,16-triene
  参考文献：
  名称：

  Novel vitamin D3 antipsoriatic antedrugs: 16-En-22-oxa-1α,25-(OH)2D3 analogs

  摘要：

  A series of 16-en-22-oxa-derivatives of vitamin D-3 based on the structure of maxacalcitol (2) were prepared. Maxacalcitol is currently used topically for the treatment of psoriasis and is recognized as the most successful antedrug of natural vitamin D-3 because it retains the original antiproliferative activity of calcitriol without increased calcemic activity. We introduced 16-olefinic functionality to accelerate the oxidative metabolism of the drug in liver, presumed to be essential for the reduction of calcemic activity, and modified the side-chain moiety by placing the 22-oxygen on the more labile allylic carbon center. Novel 22-oxa analogs (7a-i), carrying either the 24-alkynyl bond or 24-hydroxy functionality in addition to the 16-double bond were synthesized and their pharmacokinetics were evaluated. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.034