(3β,20S)-pregn-5-ene-22S-benzylbut-24-enylcarbamate | 1313610-99-9

• 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: (3β,20S)-pregn-5-ene-22S-benzylbut-24-enylcarbamate
• CAS: 1313610-99-9
• 化学式: C₃₃H₄₇NO₃
• 分子量: 505.741
• InChiKey: YJGDVFDCBFBCIU-GMXFLPSGSA-N

物化性质

• 熔点：
  151-152 °C
• 沸点：
  630.3±48.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3β,20S)-pregn-5-ene-22S-benzylbut-24-enylcarbamate 在 dicarbonylacetylacetonato rhodium (I) 、 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 、 6,6′-[(3,3′-二叔丁基-5,5′-二甲氧基-1,1′-二苯基-2,2′-二基)双(氧)]双(二苯并[d,f][1,3,2]二噁磷杂庚英) 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 65.0 ℃ 、500.01 kPa 条件下， 反应 66.02h， 生成 25-desmethylveramiline
  参考文献：
  名称：

  Synthesis and biological evaluation of desmethylveramiline, a micromolar Hedgehog inhibitor

  摘要：

  Desmethylveramiline (1), an aza steroid analogue of veramiline was designed as a surrogate for cyclopamine, a reference antagonist of the Sonic Hedgehog (Shh) pathway. Desmethyveramiline (1) was prepared in seven steps from commercially available Fernholtz acid using the hydroformylation of a terminal olefine as the key step for the construction of the piperidine appendage. In two assays (i) the inhibition of the Shh-induced Gli-dependent luciferase activity in Shh-light2 cells, (ii) the inhibition of the SAG-induced differentiation of the mesenchymal C3H10T1/2cells, desmethylveramiline (1) is an inhibitor in the mu M range comparable to cyclopamine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.103
• 作为产物：
  描述：

  (20S)-3β-(tert-butyldimethylsilanyloxy)-20-methyl-pregn-5-en-21-ol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (3β,20S)-pregn-5-ene-22S-benzylbut-24-enylcarbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of desmethylveramiline, a micromolar Hedgehog inhibitor

  摘要：

  Desmethylveramiline (1), an aza steroid analogue of veramiline was designed as a surrogate for cyclopamine, a reference antagonist of the Sonic Hedgehog (Shh) pathway. Desmethyveramiline (1) was prepared in seven steps from commercially available Fernholtz acid using the hydroformylation of a terminal olefine as the key step for the construction of the piperidine appendage. In two assays (i) the inhibition of the Shh-induced Gli-dependent luciferase activity in Shh-light2 cells, (ii) the inhibition of the SAG-induced differentiation of the mesenchymal C3H10T1/2cells, desmethylveramiline (1) is an inhibitor in the mu M range comparable to cyclopamine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.103