7-去氢胆固醇 5,6-氧化物 | 95841-71-7

• 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
• 中文名称: 7-去氢胆固醇 5,6-氧化物
• 中文别名: 7-去氢胆固醇5,6-氧化物
• 英文名称: 5β,6β-epoxycholest-7-en-3β-ol
• 英文别名: 7-Dehydrocholesterol 5,6-oxide；(1S,2R,5S,7S,9R,12R,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-10-en-5-ol
• CAS: 95841-71-7
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: HQJPDAPYXZGRSF-RMXJHBPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-去氢胆固醇 5,6-氧化物 在 phosphate buffer 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 cholest-6-ene-3beta,5beta,8beta-triol
  参考文献：
  名称：

  Stereoselective synthesis and solvolytic behavior of the isomeric 7-dehydrocholesterol 5,6-oxides

  摘要：

  DOI：

  10.1021/jo00211a009
• 作为产物：
  描述：

  7α-bromocholest-5-en-3β-ol benzoate 在 氢氧化钾 、 potassium tert-butylate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二甲基亚砜 、 苯 为溶剂， 反应 7.5h， 生成 7-去氢胆固醇 5,6-氧化物
  参考文献：
  名称：

  Stereoselective synthesis and solvolytic behavior of the isomeric 7-dehydrocholesterol 5,6-oxides

  摘要：

  DOI：

  10.1021/jo00211a009

文献信息

• Meiosis regulating compounds
  申请人：——

  公开号：US20010005757A1

  公开（公告）日：2001-06-28

  Certain compounds, structurally related to natural compounds which can be extracted i.a. from bull testes and from human follicular fluid, can be used for regulating the meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives. These compounds have the structural formula 1 wherein the substituents are as defined in the specification.

  某些化合物在结构上与可以从公牛睾丸和人类卵泡液中提取的天然化合物相关，可用于调节卵母细胞和男性生殖细胞中的减数分裂。其中一些化合物对治疗不孕症有用，而其他化合物则可用作避孕药。这些化合物具有结构式，其中取代基如规范中定义。
• 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.
• MEIOSIS REGULATING COMPOUNDS
  申请人：NOVO NORDISK A/S

  公开号：EP0946584A1

  公开（公告）日：1999-10-06
• US6486145B2
  申请人：——

  公开号：US6486145B2

  公开（公告）日：2002-11-26
• US6759400B2
  申请人：——

  公开号：US6759400B2

  公开（公告）日：2004-07-06