(3β,20R)-3-<(tert-butyldimethylsilyl)oxy>-24-norchol-5-en-23-al | 134952-66-2

• 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: (3β,20R)-3-<(tert-butyldimethylsilyl)oxy>-24-norchol-5-en-23-al
• 英文别名: 3β-DMTBS-24-norchol-5-en-22-al
• CAS: 134952-66-2
• 化学式: C₂₉H₅₀O₂Si
• 分子量: 458.8
• InChiKey: OVLDUHBWHKOYRI-OHPSOFBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.18
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3β,20R)-3-<(tert-butyldimethylsilyl)oxy>-24-norchol-5-en-23-al 在 吡啶 、 二环己烷并-18-冠醚-6 、 potassium hydride 、 borane tert-butylamine 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 194.59h， 生成 (3β,24R,S)-24-ethyl-24-thioniacholest-5-en-3-ol iodide
  参考文献：
  名称：

  Synthesis, specificity, and antifungal activity of inhibitors of the Candida albicans .DELTA.24-sterol methyltransferase

  摘要：

  A series of side chain modified analogues of cholesterol and lanosterol (1-10) have been synthesized and evaluated as inhibitors of the Candida albicans DELTA-24-sterol methyltransferase. Two sterol substrate analogues 1 and 2 which contained a 24-thia substituent were relatively modest inhibitors of the enzyme (K(i) = 1.5-72-mu-M). Compounds which mimic the carbocation intermediates proposed for the methyltransferase reaction, including sulfonium salts 4-6, amidines 7 and 8, and imidazoles 9 and 10 were substantially more potent inhibitors (K(i) = 5-500 nM). All of the sterol analogues examined displayed less than 10-fold selectivity for inhibition of the methyltransferase versus the rat liver DELTA-24-sterol reductase. The sterol analogues were tested for in vitro antifungal activity against C. albicans, Candida tropicalis, and Torulopsis glabrata. The minimum inhibitory concentrations versus C. albicans correlated well with the K(i) values for methyltransferase inhibition, and the potency of several compounds approached that of amphotericin B, although only modest fungicidal activity was observed.

  DOI：

  10.1021/jm00079a012
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 草酰氯 、 mercury(II) diacetate 、 potassium 2-methylbutan-2-olate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 8.58h， 生成 (3β,20R)-3-<(tert-butyldimethylsilyl)oxy>-24-norchol-5-en-23-al
  参考文献：
  名称：

  Synthesis, specificity, and antifungal activity of inhibitors of the Candida albicans .DELTA.24-sterol methyltransferase

  摘要：

  A series of side chain modified analogues of cholesterol and lanosterol (1-10) have been synthesized and evaluated as inhibitors of the Candida albicans DELTA-24-sterol methyltransferase. Two sterol substrate analogues 1 and 2 which contained a 24-thia substituent were relatively modest inhibitors of the enzyme (K(i) = 1.5-72-mu-M). Compounds which mimic the carbocation intermediates proposed for the methyltransferase reaction, including sulfonium salts 4-6, amidines 7 and 8, and imidazoles 9 and 10 were substantially more potent inhibitors (K(i) = 5-500 nM). All of the sterol analogues examined displayed less than 10-fold selectivity for inhibition of the methyltransferase versus the rat liver DELTA-24-sterol reductase. The sterol analogues were tested for in vitro antifungal activity against C. albicans, Candida tropicalis, and Torulopsis glabrata. The minimum inhibitory concentrations versus C. albicans correlated well with the K(i) values for methyltransferase inhibition, and the potency of several compounds approached that of amphotericin B, although only modest fungicidal activity was observed.

  DOI：

  10.1021/jm00079a012

文献信息

• Synthesis of 23-ketocholestane derivatives with different side-chain lengths (asterosapogenin analogs)
  作者：I. A. Kutnevich、I. G. Reshetova、E. I. Chernoburova、A. V. Kamernitskii

  DOI：10.1007/bf00958594

  日期：1991.4

  Syntheses were developed for 23-ketoasterosapogenin analogs with various side-chain lengths from dimethyl(tert-butyl)silyloxypregnenolone (DMTBS-pregnenolone) through 20-hydroxy-23-carboxylates or 22-acetylenic (C5, C6) derivatives by reduction and allylic rearrangement with concurrent oxidation of the intermediate 23-hydroxy-27-nor- and 27-nor-26-methylcholestanes.