5α,6α-epoxyandrostane-3β,17β-diol | 29752-14-5

• 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,6α-epoxyandrostane-3β,17β-diol
• 英文别名: 3β,17β-dihydroxy-5,6α-epoxy-5α-androstan；5α,6α-Epoxy-3β,17β-dihydroxy-androstan；5,6α-epoxyandrostan-3β,17β-diol；5,6α-epoxy-5α-androstane-3β,17β-diol；5,6α-Epoxy-5α-androstan-3β,17β-diol；(1S,2R,5S,7R,9S,11S,12S,15S,16S)-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecane-5,15-diol
• CAS: 29752-14-5
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: QNCNODDNQFHTAE-ZEMYGLBYSA-N

物化性质

• 沸点：
  452.2±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α,6α-epoxyandrostane-3β,17β-diol 在 哌啶 、 吡啶 、 chromium(VI) oxide 作用下， 生成 6α-hydroxy-androst-4-ene-3,17-dione
  参考文献：
  名称：

  6-Methyl Steroids in the Androstane Series¹

  摘要：

  DOI：

  10.1021/ja01550a073
• 作为产物：
  描述：

  雄烯二醇 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到5α,6α-epoxyandrostane-3β,17β-diol
  参考文献：
  名称：

  C-6α-和C-7α取代的甾体芳香化酶抑制剂：哪个更好？合成，生化评估，对接研究和构效关系。

  摘要：

  研究了C-6α和C-7α雄烷酮，以揭示其中的哪个位置更易于官能化以实现优异的芳香化酶抑制作用。在第一个系列中，对C-6和C-7甲基衍生物的研究导致了非常活泼的化合物9，IC50为0.06μM，Ki = 0.025μM（竞争性抑制）。在第二系列中，对C-6和C-7烯丙基衍生物的研究导致了这项工作中最佳的芳香化酶抑制剂13，IC50为0.055μM，Ki = 0.0225μM（不可逆抑制）。除了这些发现外，可以得出结论，C-6α位置比C-7α更好的功能化，除了同时存在一个C-4取代基时。另外，甲基是最好的取代基，其次是烯丙基，其次是羟基。为了合理化最佳抑制剂13的构效关系，

  DOI：

  10.1021/acs.jmedchem.9b00157

文献信息

• Wada, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 684,685
  作者：Wada

  DOI：——

  日期：——
• 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.
• Highly β‐Selective Epoxidation of Δ ⁵ ‐Unsaturated Steroids Catalyzed by Ketones
  作者：Dan Yang、Guan‐Sheng Jiao

  DOI：10.1002/1521-3765(20001002)6:19<3517::aid-chem3517>3.0.co;2-#

  日期：2000.10.2

  A general catalytic and environmentally friendly method for beta-epoxidation of Delta(5)-unsaturated steroids has been developed, which uses ketones as the catalysts and Oxone as the terminal oxidant. A whole range of Delta(5)-unsaturated steroids, which bear different functional groups such as hydroxyl, carbonyl, acetyl, or ketal, as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5 beta,5 beta-epoxides with excellent beta-selectivities and high yields.
• Steroids. CXXIV.¹ Studies in Cyano Steroids. Part I. The Synthesis of a Series of C-6-Cyano Steroid Hormones
  作者：A. Bowers、E. Denot、María Blanca Sánchez、L. M. Sánchez-Hidalgo、H. J. Ringold

  DOI：10.1021/ja01528a053

  日期：1959.10
• Madaewa et al., Zhurnal Obshchei Khimii, 1940, vol. 10, p. 213,214
  作者：Madaewa et al.

  DOI：——

  日期：——