11β-hydroxyestrone 3,11-diacetate | 17521-91-4

• 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: 11β-hydroxyestrone 3,11-diacetate
• 英文别名: 3,11β-diacetoxy-estra-1,3,5(10)-trien-17-one；3,11β-Diacetoxy-oestra-1,3,5(10)-trien-17-on；Estra-1,3,5(10)-trien-17-one, 3,11-bis(acetyloxy)-, (11beta)-；[(8S,9S,11S,13S,14S)-3-acetyloxy-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-11-yl] acetate
• CAS: 17521-91-4
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: WLWVQTWOYOZNBO-WODKUCBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11β-hydroxyestrone 3,11-diacetate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 11β-acetoxyestrone
  参考文献：
  名称：

  Structure-activity relationships of estrogens: Effects of esterification of the 11β-hydroxyl group

  摘要：

  Fourteen esters (formate, acetate, propionate, butyrate, hexanoate, heptanoate, and benzoate) located at C-11 of 11 beta-hydroxyesterone and 11 beta-hydroxyestradiol-17 beta were synthesized and evaluated for uterotropic and gonadotropin release inhibition in rats, as well as their ability to displace (3H) estradiol-17 beta from the rat uterine cytosolic estrogen receptor. The most potent uterotropic agent was 11 beta-formoxyestrone which was 1,625 or 2,500 times as active as 11 beta-hydroxyesterone in the uterotropic or gonadotropin release inhibition assay, respectively. 11 beta-Formoxyestrone was 7.5 times as uterotropic as estradiol-17 beta and equal to estradiol-17 beta in inhibiting gonadotropin release. However, the most potent inhibitor of gonadotropin release was 11 beta-acetoxy-estradiol-17 beta which had 133% of the activity of estradiol-17 beta, although it had only 38% of the activity of estradiol-17 beta in the uterotropic assay. Esters larger than the acetoxy group showed sharply decreased activities in either assay. Despite the high estrogenic potency of the 11-formates or 11-acetates, they were rather weak (6% to 35% as active as estradiol-17 beta) in displacing (3H) estradiol-17 beta from the rat uterine cytosolic estrogen receptor.

  DOI：

  10.1016/0039-128x(84)90063-1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 二氯甲烷 作用下， 生成 11β-hydroxyestrone 3,11-diacetate
  参考文献：
  名称：

  Preparation and Reactions of 11-Substituted 1,3,5(10)-Estratrienes.¹ I. 11-Oxygenated Estrones and Estradiols

  摘要：

  DOI：

  10.1021/ja01542a045

文献信息

• Structure-activity relationships of estrogens: Effects of esterification of the 11β-hydroxyl group
  作者：Albert Segaloff、R.Bruce Gabbard

  DOI：10.1016/0039-128x(84)90063-1

  日期：1984.1

  Fourteen esters (formate, acetate, propionate, butyrate, hexanoate, heptanoate, and benzoate) located at C-11 of 11 beta-hydroxyesterone and 11 beta-hydroxyestradiol-17 beta were synthesized and evaluated for uterotropic and gonadotropin release inhibition in rats, as well as their ability to displace (3H) estradiol-17 beta from the rat uterine cytosolic estrogen receptor. The most potent uterotropic agent was 11 beta-formoxyestrone which was 1,625 or 2,500 times as active as 11 beta-hydroxyesterone in the uterotropic or gonadotropin release inhibition assay, respectively. 11 beta-Formoxyestrone was 7.5 times as uterotropic as estradiol-17 beta and equal to estradiol-17 beta in inhibiting gonadotropin release. However, the most potent inhibitor of gonadotropin release was 11 beta-acetoxy-estradiol-17 beta which had 133% of the activity of estradiol-17 beta, although it had only 38% of the activity of estradiol-17 beta in the uterotropic assay. Esters larger than the acetoxy group showed sharply decreased activities in either assay. Despite the high estrogenic potency of the 11-formates or 11-acetates, they were rather weak (6% to 35% as active as estradiol-17 beta) in displacing (3H) estradiol-17 beta from the rat uterine cytosolic estrogen receptor.
• Preparation and Reactions of 11-Substituted 1,3,5(10)-Estratrienes.¹ I. 11-Oxygenated Estrones and Estradiols
  作者：Barney J. Magerlein、John A. Hogg

  DOI：10.1021/ja01542a045

  日期：1958.5