11β-acetoxyestradiol-17β | 95258-51-8

• 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-acetoxyestradiol-17β
• 英文别名: 11β-Acetoxyestradiol；[(8S,9S,11S,13S,14S,17S)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-11-yl] acetate
• CAS: 95258-51-8
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: JRKHEAMPOXYWLN-SIRBJWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  11β-hydroxyestrone 3,11-diacetate 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.75h， 生成 11β-acetoxyestradiol-17β
  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

文献信息

• Design of drugs involving receptor-ligand-DNA interactions
  申请人：——

  公开号：US20020064790A1

  公开（公告）日：2002-05-30

  It has been discovered that the degree of hormonal activity of candidate ligands correlates better with degree of fit into DNA than with the strength of receptor binding, and that the receptors in the steroid/thyroid hormone/vitamin A and D family alter the physiochemical properties of DNA and in concert with other transcription factors facilitate insertion of the ligand into DNA. As a result, the magnitude of the response is a function of the structure of the ligand as it related to insertion and fit into the DNA and the specificity of the response is a function of the stereochemistry of the receptor through binding to both the ligand and to the DNA. Based on these discoveries, a method is described herein for identifying drugs having increased activity as compared with the natural ligand for receptors such as the estrogenic receptors.

  人们发现，候选配体的荷尔蒙活性程度与 DNA 的匹配程度的相关性比与受体结合强度的相关性要好，类固醇/甲状腺激素/维生素 A 和 D 家族中的受体会改变 DNA 的理化性质，并与其他转录因子一起促进配体插入 DNA。因此，反应的大小是配体结构的函数，因为它与插入和适合 DNA 有关，而反应的特异性则是受体通过与配体和 DNA 结合的立体化学的函数。基于这些发现，本文介绍了一种方法，用于鉴定与雌激素受体等受体的天然配体相比活性更强的药物。
• Systems and methods for rapid evaluation and design of molecules for predicted biological activity
  申请人：——

  公开号：US20040002052A1

  公开（公告）日：2004-01-01

  The computer-based systems and methods are for rapidly evaluating molecules for suspected biological activity and relative potency, and for designing molecules for desired biological activity. The systems and methods enable rapid screening of large molecular databases using one or more search engines designed to identify molecules predicted to possess specific biological activities.

  基于计算机的系统和方法用于快速评估分子的可疑生物活性和相对效力，以及设计具有所需生物活性的分子。这些系统和方法可利用一个或多个搜索引擎快速筛选大型分子数据库，以识别预测具有特定生物活性的分子。
• DESIGN OF DRUGS INVOLVING RECEPTOR-LIGAND-DNA INTERACTIONS
  申请人：Hendry, Lawrence B.

  公开号：EP0740708B1

  公开（公告）日：2004-08-04
• US5705335A
  申请人：——

  公开号：US5705335A

  公开（公告）日：1998-01-06
• US5888741A
  申请人：——

  公开号：US5888741A

  公开（公告）日：1999-03-30