11-allyl-11,17β-dihydroxy-3-methoxy-estra-1,3,5(10),8(9)-tetraene 17-acetate | 1056884-76-4

• 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: 11-allyl-11,17β-dihydroxy-3-methoxy-estra-1,3,5(10),8(9)-tetraene 17-acetate
• 英文别名: [(13S,14S,17S)-11-hydroxy-3-methoxy-13-methyl-11-prop-2-enyl-7,12,14,15,16,17-hexahydro-6H-cyclopenta[a]phenanthren-17-yl] acetate
• CAS: 1056884-76-4
• 化学式: C₂₄H₃₀O₄
• 分子量: 382.5
• InChiKey: NZVCQSJCEHZRCW-ANJPWDGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11-allyl-11,17β-dihydroxy-3-methoxy-estra-1,3,5(10),8(9)-tetraene 17-acetate 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.33h， 以35%的产率得到11-allyl-17β-hydroxy-3-methoxy-estra-1,3,5(10),8(9),11-pentaene
  参考文献：
  名称：

  Synthesis and in vivo evaluation of 11-substituted estradiol derivatives as anti-implantation agents

  摘要：

  Synthesis of 11-substituted estradiol derivatives (12-17) has been carried out by the Grignard reaction with alkyl, allyl, and benzyl halides on 17 beta-hydroxy-3-methoxy-11-oxo-estra-1,3,5(10), 8(9)-tetraene (10). The novel compounds (10 and 12-17) were evaluated for their preliminary post-coital contraceptive (anti-implantation) activity in Sprague-Dawley rats. The tested compounds were administered orally and showed significant anti-implantation activity. Compound 13 is the most potent compound in the series which showed 100% contraceptive efficacy at 1.25 mg kg (1). (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.093
• 作为产物：
  描述：

  11-allyl-11,17β-dihydroxy-3-methoxy-estra-1,3,5(10),8(9)-tetraene 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以64%的产率得到11-allyl-11,17β-dihydroxy-3-methoxy-estra-1,3,5(10),8(9)-tetraene 17-acetate
  参考文献：
  名称：

  Synthesis and in vivo evaluation of 11-substituted estradiol derivatives as anti-implantation agents

  摘要：

  Synthesis of 11-substituted estradiol derivatives (12-17) has been carried out by the Grignard reaction with alkyl, allyl, and benzyl halides on 17 beta-hydroxy-3-methoxy-11-oxo-estra-1,3,5(10), 8(9)-tetraene (10). The novel compounds (10 and 12-17) were evaluated for their preliminary post-coital contraceptive (anti-implantation) activity in Sprague-Dawley rats. The tested compounds were administered orally and showed significant anti-implantation activity. Compound 13 is the most potent compound in the series which showed 100% contraceptive efficacy at 1.25 mg kg (1). (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.093

文献信息

• Synthesis and in vivo evaluation of 11-substituted estradiol derivatives as anti-implantation agents
  作者：Indra Dwivedy、Atul Gupta、Arvinder Grover、Vandana Srivastava、Man Mohan Singh、Suprabhat Ray

  DOI：10.1016/j.bmcl.2008.05.093

  日期：2008.7

  Synthesis of 11-substituted estradiol derivatives (12-17) has been carried out by the Grignard reaction with alkyl, allyl, and benzyl halides on 17 beta-hydroxy-3-methoxy-11-oxo-estra-1,3,5(10), 8(9)-tetraene (10). The novel compounds (10 and 12-17) were evaluated for their preliminary post-coital contraceptive (anti-implantation) activity in Sprague-Dawley rats. The tested compounds were administered orally and showed significant anti-implantation activity. Compound 13 is the most potent compound in the series which showed 100% contraceptive efficacy at 1.25 mg kg (1). (c) 2008 Elsevier Ltd. All rights reserved.