(8R,9S,10R,13S,14S,17S)-17-(1-Ethoxy-vinyl)-13-ethyl-3-methoxy-16-methylene-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol | 192722-11-5

• 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: (8R,9S,10R,13S,14S,17S)-17-(1-Ethoxy-vinyl)-13-ethyl-3-methoxy-16-methylene-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
• CAS: 192722-11-5
• 化学式: C₂₅H₃₆O₃
• 分子量: 384.559
• InChiKey: WDQJYCBFYUYBEG-ZWYIGRMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (8R,9S,10R,13S,14S,17S)-17-(1-Ethoxy-vinyl)-13-ethyl-3-methoxy-16-methylene-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol 在 盐酸 作用下， 反应 8.0h， 以31.6 g的产率得到16-methylene-17β-hydroxy-18-methyl-19-nor-17α-pregn-4-en-3,20-dione
  参考文献：
  名称：

  Synthesis and biological activity of a new progestogen, 16-methylene-17α-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione acetate

  摘要：

  The progestational activity of second- and third-generation progestins in oral contraceptives were markedly increased by addition of an 18-methyl group. A new progestin, the 18-methyl analog of Nestorone, 16-methylene-17 alpha-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione acetate (10), was synthesized. The relative binding affinity and biologic activity of 10 was compared with Nestorone, levonorgestrel. and progesterone using a binding assay for rat progesterone receptors, the Clauberg assay in the rabbit. and by assessing pregnancy maintenance in the rat. These studies, as summarized in Table 4, show that 10 is three to ten times more potent than Nestorone. The addition of the 18-merhyl group to Nestorone markedly increased its potency as noted above. but is unlikely to change its rate of delivery from sustained release systems. 10 should be ideally suited for administration by implants or small skin patches. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00109-9
• 作为产物：
  描述：

  在 叔丁基锂 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 5.5h， 生成 (8R,9S,10R,13S,14S,17S)-17-(1-Ethoxy-vinyl)-13-ethyl-3-methoxy-16-methylene-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  Synthesis and biological activity of a new progestogen, 16-methylene-17α-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione acetate

  摘要：

  The progestational activity of second- and third-generation progestins in oral contraceptives were markedly increased by addition of an 18-methyl group. A new progestin, the 18-methyl analog of Nestorone, 16-methylene-17 alpha-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione acetate (10), was synthesized. The relative binding affinity and biologic activity of 10 was compared with Nestorone, levonorgestrel. and progesterone using a binding assay for rat progesterone receptors, the Clauberg assay in the rabbit. and by assessing pregnancy maintenance in the rat. These studies, as summarized in Table 4, show that 10 is three to ten times more potent than Nestorone. The addition of the 18-merhyl group to Nestorone markedly increased its potency as noted above. but is unlikely to change its rate of delivery from sustained release systems. 10 should be ideally suited for administration by implants or small skin patches. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00109-9