3α-acetoxy-24-nor-5β-cholane-23-carbonitrile | 911472-94-1

• 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: 3α-acetoxy-24-nor-5β-cholane-23-carbonitrile
• 英文别名: 3α-acetoxy-5β-cholane-24-nitrile；3α-Acetoxy-5β-cholan-24-nitril；3α-Acetoxy-5β-cholanonitril
• CAS: 911472-94-1
• 化学式: C₂₆H₄₁NO₂
• 分子量: 399.617
• InChiKey: SUCBJYLNYQIANN-OUPAKXGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3α-acetoxy-24-nor-5β-cholane-23-carbonitrile 在 chromium(VI) oxide 作用下， 生成 24-phenyl-5β-cholane-3,24-dione
  参考文献：
  名称：

  Ercoli; De Ruggieri, Il Farmaco, scienza e tecnica, 1951, vol. 6, p. 438,443

  摘要：

  DOI：
• 作为产物：
  描述：

  3α-acetoxy-5β-cholan-24-oic acid amide 在 氯化亚砜 作用下， 生成 3α-acetoxy-24-nor-5β-cholane-23-carbonitrile
  参考文献：
  名称：

  Ercoli; De Ruggieri, Il Farmaco, scienza e tecnica, 1951, vol. 6, p. 438,443

  摘要：

  DOI：

文献信息

• Synthesis of 24-(Piperidin-1-yl, Morpholin-4-yl and 4-Methylpiperazin-1-yl)-5β-cholan-3α-ols and Four Hydroxylated 23-(4,5-Dihydroimidazol-2-yl)-24-nor-5β-cholanes
  作者：Thi Thu Huong Nguyen、Jiří Protiva、Eva Klinotová、Jiří Urban、Miroslav Protiva

  DOI：10.1135/cccc19970471

  日期：——

  Lithocholic (1a), chenodeoxycholic (1b), deoxycholic (1c) and cholic acid (1d) were used for the synthesis of the title compouds. Reactions of O-acetyllithocholic acid chloride with piperidine, morpholine and 1-methylpiperazine gave the corresponding amides 2a-2c which were reduced with lithium aluminium hydride to 24-(piperidin-1-yl)-5β-cholan-3α-ol (3a) and analogues 3b and 3c. Heating of the acids 1a-1d with ethylenediamine monotosylate afforded 23-(4,5-dihydroimidazol-2-yl)-24-nor-5β-cholan-3α-ol (4a) and analogues 4b-4d. Compound 4a was similarly obtained from 3α-acetoxy-24-nor-5β-cholane-23-carbonitrile. Identity of the products was corroborated by spectral characterization. Some of the products (in the form of salts) were tested for cancerostatic and antimicrobial activities in vitro with partially promising results.

  石胆酸（1a），陈胆酸（1b），去氧胆酸（1c）和胆酸（1d）被用于合成标题化合物。将O-乙酰石胆酸氯化物与哌啶，吗啉和1-甲基哌嗪反应，得到相应的酰胺2a-2c，然后用氢化铝锂还原为24-(哌啶-1-基)-5β-胆烷-3α-醇（3a）及类似物3b和3c。将酸1a-1d与乙二胺单对甲苯磺酸酯加热，得到23-(4,5-二氢咪唑-2-基)-24-去-5β-胆烷-3α-醇（4a）及类似物4b-4d。化合物4a也可以从3α-乙酰氧基-24-去-5β-胆烷-23-碳腈中类似地获得。通过光谱表征证实了产物的身份。其中一些产物（以盐的形式）经过体外测试，显示出部分有希望的抗癌和抗微生物活性。
• Syntheses with stable isotopes: Synthesis of deuterium and¹³C labeled bile acids
  作者：D. L. Hachey、P. A. Szczepanik、O. W. Berngruber、P. D. Klein

  DOI：10.1002/jlcr.2590090412

  日期：1973.10

  A series of 5β-cholanic acids labeled with deuterium in the A ring were prepared by exchange labeling of the corresponding ketone by column chromatography on deuterated alumina. Factors affecting yield and labeling efficiency are discussed. 5β-Cholanic acids labeled with 13C in the carboxyl position were prepared by treatment of the corresponding 23-chloro-24-norcholane with sodium cyanide-13C followed by alkaline hydrolysis of the nitrile. The intermediates in the synthesis were characterized by high resolution NMR spectroscopy. Mass spectra are also reported for the 13C labeled products.

  通过在氚化氧化铝上进行柱层析，对相应的酮进行交换标记，制备了一系列在 A 环中用氘标记的 5β-cholanic 酸。本文讨论了影响产率和标记效率的因素。用氰化钠-13C 处理相应的 23-氯-24-正胆烷，然后碱水解腈，制备了在羧基位置标记 13C 的 5β-Cholanic 酸。合成过程中的中间产物通过高分辨率核磁共振光谱进行了表征。同时还报告了 13C 标记产物的质谱图。