[(1S,2S,10S,13R,14S,17R,18S)-6-acetyl-17-ethynyl-2,18-dimethyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-yl] acetate | 160458-64-0

• 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: [(1S,2S,10S,13R,14S,17R,18S)-6-acetyl-17-ethynyl-2,18-dimethyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-yl] acetate
• CAS: 160458-64-0
• 化学式: C₂₇H₃₄O₄
• 分子量: 422.565
• InChiKey: XITPNRCRIUDRQN-QDIVAEBDSA-N

物化性质

• 沸点：
  526.4±50.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S,2S,10S,13R,14S,17R,18S)-6-acetyl-17-ethynyl-2,18-dimethyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-yl] acetate 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.0h， 以84%的产率得到1-(5alpha,17 alpha-17-Hydroxyandrost-2-en-20-yno[3,2-b]-furan-5'-yl)ethanone
  参考文献：
  名称：

  Androgen Receptor Affinity of 5'-Acyl Furanosteroids

  摘要：

  Syntheses of 5'-acyl furanosteroids are described from the corresponding unsubstituted [3,2-b]furanosteroids using acid anhydrides and acid chlorides in the presence or absence of Lewis acids. New methods have been developed to prepare 5'-acetyl derivatives: reduction of a 5'-trichloroacetyl intermediate either by sodium formaldehyde sulfoxylate or with 10% Pd/C. Most of these 5'-acyl derivatives bind to the rat ventral prostate androgen receptor. However the antiandrogenic activity was diminished when compared with 4, 5'-methylsulfonyl furanosteroid. Biological studies revealed that 5'-acyl furanosteroids were either androgens or modest antiandrogens. The electrostatic potential maps of the substructures of 3, 4, and 5'-acetyl syn- and anti-furanosteroids showed striking differences which may explain, to some extent, the lack of significant antiandrogenic activity of 5'-acyl furanosteroids.

  DOI：

  10.1021/jm00050a019
• 作为产物：
  描述：

  (5α,17β)-Androst-2-eno<3,2-b>furan-17-ol 在 吡啶 、 4-二甲氨基吡啶 、 氯化二乙基铝 、 二甲基亚砜 、 三氟乙酸酐 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 [(1S,2S,10S,13R,14S,17R,18S)-6-acetyl-17-ethynyl-2,18-dimethyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-yl] acetate
  参考文献：
  名称：

  Androgen Receptor Affinity of 5'-Acyl Furanosteroids

  摘要：

  Syntheses of 5'-acyl furanosteroids are described from the corresponding unsubstituted [3,2-b]furanosteroids using acid anhydrides and acid chlorides in the presence or absence of Lewis acids. New methods have been developed to prepare 5'-acetyl derivatives: reduction of a 5'-trichloroacetyl intermediate either by sodium formaldehyde sulfoxylate or with 10% Pd/C. Most of these 5'-acyl derivatives bind to the rat ventral prostate androgen receptor. However the antiandrogenic activity was diminished when compared with 4, 5'-methylsulfonyl furanosteroid. Biological studies revealed that 5'-acyl furanosteroids were either androgens or modest antiandrogens. The electrostatic potential maps of the substructures of 3, 4, and 5'-acetyl syn- and anti-furanosteroids showed striking differences which may explain, to some extent, the lack of significant antiandrogenic activity of 5'-acyl furanosteroids.

  DOI：

  10.1021/jm00050a019