6β-thiosemicarbazone-B-norcholest-3,5-diene | 1398623-57-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6β-thiosemicarbazone-B-norcholest-3,5-diene
• CAS: 1398623-57-8
• 化学式: C₂₈H₄₅N₃S
• 分子量: 455.751
• InChiKey: UURNMUFWRASQEZ-XPVYSPFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  50.41
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norcholestane 在 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇-D1 为溶剂， 反应 3.5h， 生成 6β-thiosemicarbazone-B-norcholest-3,5-diene
  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

文献信息

• Synthesis and in vitro antiproliferative evaluation of some ring B abeo-sterols
  作者：Chunfang Gan、Lianghua Fan、Jianguo Cui、Yanmin Huang、Yanxiao Jiao、Wanxin Wei

  DOI：10.1016/j.steroids.2012.05.005

  日期：2012.9

  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.