N-(2-thioethyl)-3α-hydroxy-5β-cholan-24-amide | 1357360-25-8

• 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: N-(2-thioethyl)-3α-hydroxy-5β-cholan-24-amide
• 英文别名: (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-(2-sulfanylethyl)pentanamide
• CAS: 1357360-25-8
• 化学式: C₂₆H₄₅NO₂S
• 分子量: 435.715
• InChiKey: ZFHNWASTILQYRK-GBURMNQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  49.33
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  石胆酸 在 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 N-(2-thioethyl)-3α-hydroxy-5β-cholan-24-amide
  参考文献：
  名称：

  Bile acid–cysteamine conjugates: Structural properties, gelation, and toxicity evaluation

  摘要：

  Design, synthesis, and characterization of six novel bile acid-cysteamine conjugates together with investigation of their structural studies, gelation properties, and preliminary toxicity evaluation, are reported. Solid state properties of selected compounds were studied by means of X-ray diffraction and C-13 CPMAS NMR spectroscopy. N-(2-thioethyl)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholan-24-amide was shown to exhibit (pseudo)polymorphism, and a single crystal structure of its non-stoichiometric hydrate is reported herein. Cholyl and dehydrocholyl derivatives bearing three functionalities in their steroidal backbone were shown to undergo self-assembly leading to gelation in certain organic solvents. Preliminary morphology studies of the formed gels by scanning electron microscopy (SEM) were performed. The standard model mouse fibroblast cell line together with the MTT and NR tests were utilized for evaluating the toxicity of the prepared compounds. Lithocholyl, ursodeoxycholyl, and dehydrocholyl derivatives turned out to be relatively non-toxic in the conditions studied. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.11.006