(17beta-17-Hydroxyestra-1,3,5(10)-trieno[3,2-b]-furan-5'-yl)propanone

• 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: (17beta-17-Hydroxyestra-1,3,5(10)-trieno[3,2-b]-furan-5'-yl)propanone
• 英文别名: 1-[(1S,13R,14S,17S,18S)-17-hydroxy-18-methyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-2(10),3,5,8-tetraen-6-yl]propan-1-one
• 化学式: C₂₃H₂₈O₃
• 分子量: 352.474
• InChiKey: DXMMRNKHIXQRPX-YRRUUWTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  诺龙 在 sodium methylate 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 68.5h， 生成 (17beta-17-Hydroxyestra-1,3,5(10)-trieno[3,2-b]-furan-5'-yl)propanone
  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.