(5S,1'S)-7,9-difluoro-5-(3-methylcylohex-2-en-1-yl)-2,2,4-trimethyl 2,5-dihydro-(1H)6-oxa-1-aza-chrysene | 852359-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (5S,1'S)-7,9-difluoro-5-(3-methylcylohex-2-en-1-yl)-2,2,4-trimethyl 2,5-dihydro-(1H)6-oxa-1-aza-chrysene
• 英文别名: (5S,1'S)-7,9-difluoro-5-(3-methylcyclohex-2-en-1-yl)-2,2,4-trimethyl 2,5-dihydro-(1H)6-oxa-1-aza-chrysene；7,9-difluoro-5-(3-methylcyclohex-2-enyl)-2,2,4-trimethyl-1,2-dihydrochromeno[3,4-f]quinoline；(+)-(S)-7,9-difluoro-2,2,4-trimethyl-5-((S)-3-methylcyclohex-2-enyl)-2,5-dihydro-1H-chromeno[3,4-f]quinoline；(5S)-7,9-difluoro-2,2,4-trimethyl-5-[(1S)-3-methylcyclohex-2-en-1-yl]-1,5-dihydrochromeno[3,4-f]quinoline
• CAS: 852359-27-4
• 化学式: C₂₆H₂₇F₂NO
• 分子量: 407.503
• InChiKey: NNEGFNICKYKFDF-FYSMJZIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,1'S)-7,9-difluoro-5-(3-methylcylohex-2-en-1-yl)-2,2,4-trimethyl 2,5-dihydro-(1H)6-oxa-1-aza-chrysene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以4%的产率得到7,9-difluoro-5-(6-methyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-2,2,4-trimethyl 2,5-dihydro-(1H)-6-oxa-1-aza-chrysene
  参考文献：
  名称：

  A Tissue-Selective Nonsteroidal Progesterone Receptor Modulator: 7,9-Difluoro-5-(3-methylcyclohex-2-enyl)-2,2,4-trimethyl-1,2-dihydrochromeno[3,4-f]quinoline

  摘要：

  The progesterone receptor plays an important role in the female reproductive system. Here we describe the discovery of a new selective progesterone receptor modulator (SPRM). In rats, the lead compound, 7,9-difluoro-5-(3-methylcyclohex-2-enyl)-2,2,4-trimethyl-1,2-dihydrochromeno[3,4-f]quinoline (5c), inhibited ovulation and showed full efficacy in uterine and vaginal tissue but was a mixed partial agonist/antagonist in breast tissue. The compound also suppressed ovulation in monkeys, but in contrast to currently approved steroidal PR agonists, it did not suppress estradiol levels.

  DOI：

  10.1021/jm8004256
• 作为产物：
  描述：

  7,9-difluoro-5-(3-methylcylohex-2-en-1-yl)-2,2,4-trimethyl 2,5-dihydro-(1H)6-oxa-1-aza-chrysene 生成 (5S,1'S)-7,9-difluoro-5-(3-methylcylohex-2-en-1-yl)-2,2,4-trimethyl 2,5-dihydro-(1H)6-oxa-1-aza-chrysene 、 7,9-difluoro-5-(3-methylcylohex-2-en-1-yl)-2,2,4-trimethyl 2,5-dihydro-(1H)6-oxa-1-aza-chrysene
  参考文献：
  名称：

  A Tissue-Selective Nonsteroidal Progesterone Receptor Modulator: 7,9-Difluoro-5-(3-methylcyclohex-2-enyl)-2,2,4-trimethyl-1,2-dihydrochromeno[3,4-f]quinoline

  摘要：

  The progesterone receptor plays an important role in the female reproductive system. Here we describe the discovery of a new selective progesterone receptor modulator (SPRM). In rats, the lead compound, 7,9-difluoro-5-(3-methylcyclohex-2-enyl)-2,2,4-trimethyl-1,2-dihydrochromeno[3,4-f]quinoline (5c), inhibited ovulation and showed full efficacy in uterine and vaginal tissue but was a mixed partial agonist/antagonist in breast tissue. The compound also suppressed ovulation in monkeys, but in contrast to currently approved steroidal PR agonists, it did not suppress estradiol levels.

  DOI：

  10.1021/jm8004256

文献信息

• A Tissue-Selective Nonsteroidal Progesterone Receptor Modulator: 7,9-Difluoro-5-(3-methylcyclohex-2-enyl)-2,2,4-trimethyl-1,2-dihydrochromeno[3,4-<i>f</i>]quinoline
  作者：Bijan Pedram、Arjan van Oeveren、Dale E. Mais、Keith B. Marschke、Pieter M. Verbost、Marinus B. Groen、Lin Zhi

  DOI：10.1021/jm8004256

  日期：2008.7

  The progesterone receptor plays an important role in the female reproductive system. Here we describe the discovery of a new selective progesterone receptor modulator (SPRM). In rats, the lead compound, 7,9-difluoro-5-(3-methylcyclohex-2-enyl)-2,2,4-trimethyl-1,2-dihydrochromeno[3,4-f]quinoline (5c), inhibited ovulation and showed full efficacy in uterine and vaginal tissue but was a mixed partial agonist/antagonist in breast tissue. The compound also suppressed ovulation in monkeys, but in contrast to currently approved steroidal PR agonists, it did not suppress estradiol levels.