3,7-dioxo-24-cholanyl methansulfonate | 1417402-85-7

• 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: 3,7-dioxo-24-cholanyl methansulfonate
• 英文别名: [(4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7-dioxo-2,4,5,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl] methanesulfonate
• CAS: 1417402-85-7
• 化学式: C₂₅H₄₀O₅S
• 分子量: 452.656
• InChiKey: JSWIGZKSMZEZSA-AWOZODTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,7-dioxo-24-cholanyl methansulfonate 在 吡啶 、 sodium azide 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(thiophene-2-sulfonyl)-3,7-dioxo-5β-cholan-24-amine
  参考文献：
  名称：

  Synthesis and antitumor activity of N-sulfonyl-3,7-dioxo-5β-cholan-24-amides, ursodeoxycholic acid derivatives

  摘要：

  A series of N-sulfonyl-3,7-dioxo-5 beta-cholan-24-amides, ursodeoxycholic acid derivatives, have been designed and synthesized in nine steps starting from ursodeoxycholic acid. The in vitro antitumor activity of the target compounds has been evaluated against HCT-116, MCF-7, K562, and SGC-7901 cell lines. The pharmacological results showed that most of the prepared compounds display excellent selective cytotoxicity toward HCT-116, MCF-7, and K562 cell lines. Particularly, compounds 10c, 10f and 10g show high inhibitory activity on these human cancer cell lines (IC50: 2.39-9.34 mu M). Conversely, all compounds are generally inactive against SGC-7901, with only 10b having IC50 below 50 mu M. Crown Copyright (c) 2012 Published by Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.09.009
• 作为产物：
  描述：

  熊去氧胆酸 在 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 氯化亚砜 、 乙醇 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.0h， 生成 3,7-dioxo-24-cholanyl methansulfonate
  参考文献：
  名称：

  Synthesis and antitumor activity of N-sulfonyl-3,7-dioxo-5β-cholan-24-amides, ursodeoxycholic acid derivatives

  摘要：

  A series of N-sulfonyl-3,7-dioxo-5 beta-cholan-24-amides, ursodeoxycholic acid derivatives, have been designed and synthesized in nine steps starting from ursodeoxycholic acid. The in vitro antitumor activity of the target compounds has been evaluated against HCT-116, MCF-7, K562, and SGC-7901 cell lines. The pharmacological results showed that most of the prepared compounds display excellent selective cytotoxicity toward HCT-116, MCF-7, and K562 cell lines. Particularly, compounds 10c, 10f and 10g show high inhibitory activity on these human cancer cell lines (IC50: 2.39-9.34 mu M). Conversely, all compounds are generally inactive against SGC-7901, with only 10b having IC50 below 50 mu M. Crown Copyright (c) 2012 Published by Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.09.009