6α-N-(3-aminopropyl)aminocholestan-3β-ol | 812650-92-3

• 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: 6α-N-(3-aminopropyl)aminocholestan-3β-ol
• CAS: 812650-92-3
• 化学式: C₃₀H₅₆N₂O
• 分子量: 460.787
• InChiKey: QJXCAEUZEVSDMK-CZGSGLPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.28
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6α-N-(3-aminopropyl)aminocholestan-3β-ol 在 lithium aluminium tetrahydride 、 碳酸氢钠 、 nickel dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 6α-N-[3N-(3-aminobutyl)aminopropyl]aminocholestan-3β-ol
  参考文献：
  名称：

  Synthesis of spermidinylcholestanol and spermidinylcholesterol, squalamine analogues

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.09.055
• 作为产物：
  描述：

  3β-acetoxy-6-hydroxyiminocholestane 在 70 lithium aluminium tetrahydride 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 36.0h， 生成 6α-N-(3-aminopropyl)aminocholestan-3β-ol
  参考文献：
  名称：

  Synthesis of spermidinylcholestanol and spermidinylcholesterol, squalamine analogues

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.09.055