3β-acetoxyl-5β-hydroxyl-6β-thiosemicarbazone-B-norandrostane | 1398623-61-4

• 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-acetoxyl-5β-hydroxyl-6β-thiosemicarbazone-B-norandrostane
• CAS: 1398623-61-4
• 化学式: C₂₂H₃₃N₃O₄S
• 分子量: 435.588
• InChiKey: XTWAIWVDAGLDPB-OIQJEXDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  114.01
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3β-acetoxyl-5β-hydroxyl-6β-thiosemicarbazone-B-norandrostane 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以68%的产率得到5β,17β-dihydroxyl-3β-acetoxyl-6-thiosemicarbazone-B-norandrostane
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative evaluation of some ring B abeo-sterols

  摘要：

  Using cholesterol, p-sitosterol, dehydroisoandrosterone and pregnenolone as starting materials, a series of 5(6 -> 7)abeo-sterols with different substituted groups and various side chains were synthesized and the antiproliferative activity of these compounds against HeLa, SMMC 7404 and MGC 7901 cells was investigated. The results revealed that the presence of a cholesterol-type side chain was very important for their cytotoxicity, and in particular a thiosemicarbazone at the C-6 position significantly enhanced the antiproliferative activity of these compounds. Although the elimination of 5-hydroxyl has no an obvious effect on their cytotoxic function, removal of the hydroxyl at the C-3 position decreased markedly the antiproliferative activity of the compounds. Some compounds have similar cytotoxic capability as cis-platin does. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.005
• 作为产物：
  描述：

  3β-acetoxyl-5,6-dioxo-5,6-secoandrostane 在 aluminum oxide 、 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 反应 5.0h， 生成 3β-acetoxyl-5β-hydroxyl-6β-thiosemicarbazone-B-norandrostane
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative evaluation of some ring B abeo-sterols

  摘要：

  Using cholesterol, p-sitosterol, dehydroisoandrosterone and pregnenolone as starting materials, a series of 5(6 -> 7)abeo-sterols with different substituted groups and various side chains were synthesized and the antiproliferative activity of these compounds against HeLa, SMMC 7404 and MGC 7901 cells was investigated. The results revealed that the presence of a cholesterol-type side chain was very important for their cytotoxicity, and in particular a thiosemicarbazone at the C-6 position significantly enhanced the antiproliferative activity of these compounds. Although the elimination of 5-hydroxyl has no an obvious effect on their cytotoxic function, removal of the hydroxyl at the C-3 position decreased markedly the antiproliferative activity of the compounds. Some compounds have similar cytotoxic capability as cis-platin does. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.005