3β-[(tetrahydropyran-2-yl)oxy]-cholestan-7-one | 782477-92-3

• 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: 3β-[(tetrahydropyran-2-yl)oxy]-cholestan-7-one
• CAS: 782477-92-3
• 化学式: C₃₂H₅₄O₃
• 分子量: 486.779
• InChiKey: NTRCNKYNETYFKT-CJJYFUCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3β-[(tetrahydropyran-2-yl)oxy]-cholestan-7-one 在 85 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 3β-hydroxy-5α-cholestan-7-one
  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-<(tetrahydropyran-2-yl)oxy>-7-oxo-cholest-5-ene 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以82%的产率得到3β-[(tetrahydropyran-2-yl)oxy]-cholestan-7-one
  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

文献信息

• Stereoselective synthesis of 7α- and 7β-aminocholestanol as potent fungicidal drugs
  作者：S Fouace、L El kihel、M Dherbomez、Y Letourneux

  DOI：10.1016/s0960-894x(01)00609-6

  日期：2001.12

  Potentially lymphotropic 7 alpha- and 7 beta -aminocholestanol were stereo selectively synthesized. In vitro bioassay studies have shown that these fungicidal lipidic derivatives possess strong antifungal activity against Candida spp resistant strains to amphotericin B, 5-fluorocytosine and azoles. (C) 2001 Elsevier Science Ltd. All rights reserved.