[(1R,2S,10S,13R,14S,17S,18S)-6-acetyl-18-methyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-yl] acetate | 160458-65-1

• 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: [(1R,2S,10S,13R,14S,17S,18S)-6-acetyl-18-methyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-yl] acetate
• CAS: 160458-65-1
• 化学式: C₂₄H₃₂O₄
• 分子量: 384.516
• InChiKey: AYSVTFKOGZOBFW-KZALKQEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  [(1R,2S,10S,13R,14S,17S,18S)-6-acetyl-18-methyl-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 3.0h， 以88%的产率得到1-(5α,17β-17-hydroxyestr-2-eno<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：

  诺龙 在 palladium on activated charcoal 吡啶 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 氢气 、 二异丁基氢化铝 、 三乙胺 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -14.0~25.0 ℃ 、344.73 kPa 条件下， 反应 44.25h， 生成 [(1R,2S,10S,13R,14S,17S,18S)-6-acetyl-18-methyl-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

文献信息

• Androgen Receptor Affinity of 5'-Acyl Furanosteroids
  作者：Virendra Kumar、James H. Ackerman、Michael D. Alexander、Malcolm R. Bell、Robert G. Christiansen、Jen S. Dung、Edward P. Jaeger、John L. Herrmann、Michael E. Krolski

  DOI：10.1021/jm00050a019

  日期：1994.11

  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.