(2S)-((13S,17S)-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl) 1-(4-sulfamoylbenzoyl)pyrrolidine-2-carboxylate | 1644459-05-1

• 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: (2S)-((13S,17S)-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl) 1-(4-sulfamoylbenzoyl)pyrrolidine-2-carboxylate
• 英文别名: (2S)-((13S,17S)-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[α]phenanthren-17-yl) 1-(4-sulfamoylbenzoyl)pyrrolidine-2-carboxylate；N7ZU267Azb；[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] (2S)-1-(4-sulfamoylbenzoyl)pyrrolidine-2-carboxylate
• CAS: 1644459-05-1
• 化学式: C₃₀H₃₆N₂O₆S
• 分子量: 552.692
• InChiKey: DDUJSLXJKGYGCG-OQDYUIEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  17β-estradiol-3-t-butyldimethylsilyl ether 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 N,N'-dicyclopropylcarbodiimide 、 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 反应 120.5h， 生成 (2S)-((13S,17S)-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl) 1-(4-sulfamoylbenzoyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  A prodrug design for improved oral absorption and reduced hepatic interaction

  摘要：

  A series of estradiol-17-beta esters of N-(p-sulfomylbenzamide)-amino acids were prepared and evaluated for systemic and hepatic estrogenic activity after oral administration in ovariectomized rats. The alkyl substitution at nitrogen of amino acids such as proline or N-methyl-alanine produced compounds that exhibit potent oral activity. The proline analog (EC508) was further evaluated along with 17 beta-estradiol (E2) and ethinyl-estradiol (EE) and compared their effects on the uterus, angiotensin and HDL-cholesterol after oral administration to ovariectomized female rats. Orally administered EC508 produced systemic estrogenic activity 10 times greater than EE and a 100 times higher activity than E2 with no influence on levels of angiotensin and HDL-cholesterol, whereas EE and E2 reduced the HDL-cholesterol and increased the angiotensine plasma levels. EC508 might offer significant advantages in indications like fertility control and HRT based on its high oral bioavailability and lack of hepatic estrogenicity. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.08.027