5α-hydroxy-6β-[4-(2-aminoethyl)imidazol-1-yl]cholestan-3β-ol | 106057-79-8

• 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: 5α-hydroxy-6β-[4-(2-aminoethyl)imidazol-1-yl]cholestan-3β-ol
• 英文别名: (3S,5R,6R,8S,9S,10R,13R,14S,17R)-6-[4-(2-aminoethyl)imidazol-1-yl]-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5-diol
• CAS: 106057-79-8
• 化学式: C₃₂H₅₅N₃O₂
• 分子量: 513.808
• InChiKey: YXLRIBHYEQBYDG-BULFVYHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-(1-((3S,5R,6R,8S,9S,10R,13R,14S,17R)-3,5-dihydroxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-6-yl)-1H-imidazol-4-yl)ethyl)acetamide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以58%的产率得到5α-hydroxy-6β-[4-(2-aminoethyl)imidazol-1-yl]cholestan-3β-ol
  参考文献：
  名称：

  Synthesis of New Alkylaminooxysterols with Potent Cell Differentiating Activities: Identification of Leads for the Treatment of Cancer and Neurodegenerative Diseases

  摘要：

  We describe here the syntheses and the biological properties of new alkylaminooxysterols. Compounds were synthesized through the trans-diaxial aminolysis of 5,6-alpha-epoxysterols with various natural amines including histamine, putrescine, spermidine, or spermine. The regioselective synthesis of these 16 new 5 alpha-hydroxyl-6 beta-aminoalkylsterols is presented. Compounds were first screened for dendrite outgrowth and cytotoxicity in vitro, and two leads were selected and further characterized. 5 alpha-Hydroxy-6 beta-[2-(1-H-imidazol-4-yl)ethylamino]cholestan -3 beta-ol, called dendrogenin A, induced growth control, differentiation, and the death of tumor cell lines representative of various cancers including metastatic melanoma and breast cancer. 5 alpha-hydroxyl-6 beta-[3-(4-aminobutylamino)propylamino]cholest-7-en-3 beta-ol, called dendrogenin B, induced neurite outgrowth on various cell lines, neuronal differentiation in pluripotent cells, and survival of normal neurones at nanomolar concentrations. In summary, we report that two new alkylaminooxysterols, dendrogenin A and dendrogenin B, are the first members of a class of compounds that induce cell differentiation at nanomolar concentrations and represent promising new leads for the treatment of cancer or neurodegenerative diseases.

  DOI：

  10.1021/jm901063e

文献信息

• Synthesis of New Alkylaminooxysterols with Potent Cell Differentiating Activities: Identification of Leads for the Treatment of Cancer and Neurodegenerative Diseases
  作者：Philippe de Medina、Michael R. Paillasse、Bruno Payré、Sandrine Silvente-Poirot、Marc Poirot

  DOI：10.1021/jm901063e

  日期：2009.12.10

  We describe here the syntheses and the biological properties of new alkylaminooxysterols. Compounds were synthesized through the trans-diaxial aminolysis of 5,6-alpha-epoxysterols with various natural amines including histamine, putrescine, spermidine, or spermine. The regioselective synthesis of these 16 new 5 alpha-hydroxyl-6 beta-aminoalkylsterols is presented. Compounds were first screened for dendrite outgrowth and cytotoxicity in vitro, and two leads were selected and further characterized. 5 alpha-Hydroxy-6 beta-[2-(1-H-imidazol-4-yl)ethylamino]cholestan -3 beta-ol, called dendrogenin A, induced growth control, differentiation, and the death of tumor cell lines representative of various cancers including metastatic melanoma and breast cancer. 5 alpha-hydroxyl-6 beta-[3-(4-aminobutylamino)propylamino]cholest-7-en-3 beta-ol, called dendrogenin B, induced neurite outgrowth on various cell lines, neuronal differentiation in pluripotent cells, and survival of normal neurones at nanomolar concentrations. In summary, we report that two new alkylaminooxysterols, dendrogenin A and dendrogenin B, are the first members of a class of compounds that induce cell differentiation at nanomolar concentrations and represent promising new leads for the treatment of cancer or neurodegenerative diseases.