3β-acetyl-7β-azidocholesterol | 156761-07-8

• 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: 3β-acetyl-7β-azidocholesterol
• 英文别名: 3-acetyl-7β-azidocholesterol
• CAS: 156761-07-8
• 化学式: C₂₉H₄₇N₃O₂
• 分子量: 469.711
• InChiKey: BQWIQEWQLGYBJX-NHGCSETBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.25
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  75.06
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3β-acetyl-7β-azidocholesterol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 7β-aminocholesterol
  参考文献：
  名称：

  Stereoselective Synthesis of 7α- and 7β-Aminocholesterol as Δ8-Δ7 Sterol Isomerase Inhibitors, with Fungicidal Activities towards Resistant Strains

  摘要：

  A mixture of epimeric 7alpha- and 7beta-aminocholesterol was shown to be a stronger inhibitor of yeast cell growth than morpholine inhibitors. In fact, this epimeric mixture inhibits Delta8-Delta7-sterol reductase. This epimeric mixture is fungicidal and active against Saccharomyces cerevisiae resistant strains. Therefore, 7alpha- and 7beta-aminocholesterol were selectively synthesized. According to in vitro bioassay studies on resistant strains such as Candida tropicalis [Amphotericin B resistant; minimum inhibitory concentration (MIC) of Amp B: 12.5 mug/mL], the MIC values for 7beta-aminocholesterol and 7alpha-aminocholesterol were found to be 0.8 mug/mL and 1.5 mug/ mL, respectively. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:23<4075::aid-ejoc4075>3.0.co;2-7
• 作为产物：
  描述：

  7α-hydroxycholest-5-en-3β-yl 3-acetate 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3β-acetyl-7β-azidocholesterol
  参考文献：
  名称：

  Stereoselective Synthesis of 7α- and 7β-Aminocholesterol as Δ8-Δ7 Sterol Isomerase Inhibitors, with Fungicidal Activities towards Resistant Strains

  摘要：

  A mixture of epimeric 7alpha- and 7beta-aminocholesterol was shown to be a stronger inhibitor of yeast cell growth than morpholine inhibitors. In fact, this epimeric mixture inhibits Delta8-Delta7-sterol reductase. This epimeric mixture is fungicidal and active against Saccharomyces cerevisiae resistant strains. Therefore, 7alpha- and 7beta-aminocholesterol were selectively synthesized. According to in vitro bioassay studies on resistant strains such as Candida tropicalis [Amphotericin B resistant; minimum inhibitory concentration (MIC) of Amp B: 12.5 mug/mL], the MIC values for 7beta-aminocholesterol and 7alpha-aminocholesterol were found to be 0.8 mug/mL and 1.5 mug/ mL, respectively. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:23<4075::aid-ejoc4075>3.0.co;2-7

文献信息

• Synthesis of spermidinylcholestanol and spermidinylcholesterol, squalamine analogues
  作者：Bassima Choucair、Michel Dherbomez、Cristos Roussakis、Laïla El Kihel

  DOI：10.1016/j.tet.2004.09.055

  日期：2004.12

  Several novel squalamine-related polyaminosterols are reported. The synthesis of 7alpha-N-[3N-(4-aminobutyl)aminopropyl]aminocholestanol I, 6alpha-N-[3N-(4-aminobutyl)aminopropyl]aminocholestanol II, 7alpha and 7beta-N-[3N-(4-aminobutyl)aminopropyl]aminocholesterol (III and IV), was accomplished from cholesterol, they provide the first examples in which spermidine is introduced in the B steroidal ring. These molecules showed comparable antibacteria and fungi activities to squalamine, and were cytotoxic on a human non-small cell bronchopulmonary carcinoma line (NSCLC-N6). Therefore, these molecules with antibiotic and cytotoxic activities are promising for immune-compromised patients in cancer chemotherapy. (C) 2004 Elsevier Ltd. All fights reserved.
• Synthesis of Aminocholesterol Derivatives with Antibiotic Properties
  作者：L. Elkihel、J. Bourass、M. Dherbomez、Y. Letourneux

  DOI：10.1080/00397919708006797

  日期：1997.6

  We report here a new family of antibiotic with fungicidal and antibacterial activity. The syntheses of five 7-amino and 7-aminoalkylcholesterol derivatives are described.