N-(3-hydroxypropyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide | 1135007-90-7

• 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: N-(3-hydroxypropyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide
• 英文别名: N-(3'-hydroxypropyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide；(4R)-N-(3-hydroxypropyl)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanamide
• CAS: 1135007-90-7
• 化学式: C₂₇H₄₇NO₅
• 分子量: 465.674
• InChiKey: PPKAMEPSZYNWAZ-OCCHXLOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  胆酸甲酯 、 3-氨基-1-丙醇 以 甲醇 为溶剂， 以40%的产率得到N-(3-hydroxypropyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide
  参考文献：
  名称：

  Syntheses and structural study of bile acid amidoalcohols

  摘要：

  Preparation, structural and thermoanalytical characterization of fourteen N-hydroxyalkyl 5 beta-cholan-24-amides have been performed in this study. The utilized techniques include liquid state and CP-MAS C-13 NMR spectroscopy, thermogravimetry, differential scanning calorimetry, and also powder and single crystal X-ray crystallography. The results were discussed and compared to each other and also to previous findings on similar compounds. One pure hydrate form was obtained. Six new single crystal structures were determined, including one hydrated chloroform solvate. Decomposition temperatures were found to correlate with the side chain length, and the number of the hydroxyl groups. The spatial direction of the groups in the steroid skeleton was also found to be relevant in predicting the thermal properties of bile acid amidoalcohols studied. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.06.006

文献信息

• The Design, Synthesis, and Characterizations of Spore Germination Inhibitors Effective against an Epidemic Strain of <i>Clostridium difficile</i>
  作者：Shiv K. Sharma、Christopher Yip、Emilio Xavier Esposito、Prateek V. Sharma、Matthew P. Simon、Ernesto Abel-Santos、Steven M. Firestine

  DOI：10.1021/acs.jmedchem.8b00632

  日期：2018.8.9

  this problem, a series of cholic acid amides were synthesized and tested against R20291. The best compound in the series was the simple phenyl amide analogue which possessed an IC50 value of 1.8 μM, more than 225 times as potent as the natural germination inhibitor, chenodeoxycholate. This is the most potent inhibitor of C. difficile spore germination described to date. QSAR and molecular modeling analysis

  艰难梭菌感染（CDI），尤其是由BI / NAP1 / 027流行株引起的艰难梭菌感染，要治疗具有挑战性。解决该疾病的一种方法是通过抑制艰难梭菌孢子的萌发来预防CDI的发展。以前的研究已经确定胆酸酰胺米磺酸，CamSA，作为孢子萌发的抑制剂。但是，CamSA对高毒力菌株R20291没有活性。为了解决这个问题，合成了一系列胆酸酰胺，并针对R20291进行了测试。该系列中最好的化合物是具有IC 50的简单苯基酰胺类似物值为1.8μM，是天然发芽抑制剂鹅脱氧胆酸盐的225倍以上。迄今为止，这是最有力的艰难梭菌孢子萌发抑制剂。QSAR和分子模型分析表明，疏水性的增加和部分电荷或极性表面积的减少与效力的增加相关。