(5R,7aR,9aR,14aR)-5,14a-methano-3-methoxy-5-methyl-7a,8,9a,10,11,12-hexahydro-5H-pyrrolo[2,1-c][1,4]-diazepine[3,4-i]benzocyclooctene-9,14-dione | 176959-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (5R,7aR,9aR,14aR)-5,14a-methano-3-methoxy-5-methyl-7a,8,9a,10,11,12-hexahydro-5H-pyrrolo[2,1-c][1,4]-diazepine[3,4-i]benzocyclooctene-9,14-dione
• 英文别名: (1R,7R,10R,13R)-16-methoxy-13-methyl-3,9-diazapentacyclo[11.7.1.01,10.03,7.014,19]henicosa-14(19),15,17-triene-2,8-dione
• CAS: 176959-84-5
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: ZGQXWWFASPRWML-DGQTTZFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 (5R,7aR,9aR,14aR)-5,14a-methano-3-methoxy-5-methyl-7a,8,9a,10,11,12-hexahydro-5H-pyrrolo[2,1-c][1,4]-diazepine[3,4-i]benzocyclooctene-9,14-dione 在 硫酸 作用下， 生成 methyl (1R,9R,10R)-10-amino-4-methoxy-1-methyltricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-9-carboxylate
  参考文献：
  名称：

  Asymmetric Syntheses, Opioid Receptor Affinities, and Antinociceptive Effects of 8-Amino-5,9-methanobenzocyclooctenes, a New Class of Structural Analogues of the Morphine Alkaloids

  摘要：

  Several 8-amino-5,9-methanobenzocyclooctenes have been prepared by asymmetric organic synthesis techniques. Opioid receptor affinity studies have revealed the virtual absence of enantioselectivity for receptor binding, particularly at the mu-receptor, for the (+)-3a-f and the (-)-3a-f series. It is noteworthy that inversion of configuration at the nitrogen-bearing carbon atom [(5S,8S,9S)-8-amino-3-hydroxy-5,9-methano-9-(methoxymethyl)-5-methylbenzocyclooctene, (+)-3a vs (5S,8S,9R)-8-amino-3-hydroxy-5,9-methanoxymethyl)-5-methylbenzocyclooctene, (dl)-22] resulted in a >10-fold increase in kappa-receptor affinity. Antinociceptive studies demonstrated that (dl)-22 was a full kappa-agonist while (+)-3a and (-)-3a did not possess kappa-activity. Although both (dl)-22 and (+)-3a/(-)-3a had high affinity for the mu-receptor, these compounds did not act as high-affinity agonists or antagonists at this receptor.

  DOI：

  10.1021/jm950817g
• 作为产物：
  描述：

  (6aR)-2-methyl-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-6,11-dione 在 三氟甲磺酸 、 氨 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 (5R,7aR,9aR,14aR)-5,14a-methano-3-methoxy-5-methyl-7a,8,9a,10,11,12-hexahydro-5H-pyrrolo[2,1-c][1,4]-diazepine[3,4-i]benzocyclooctene-9,14-dione
  参考文献：
  名称：

  Asymmetric Syntheses, Opioid Receptor Affinities, and Antinociceptive Effects of 8-Amino-5,9-methanobenzocyclooctenes, a New Class of Structural Analogues of the Morphine Alkaloids

  摘要：

  Several 8-amino-5,9-methanobenzocyclooctenes have been prepared by asymmetric organic synthesis techniques. Opioid receptor affinity studies have revealed the virtual absence of enantioselectivity for receptor binding, particularly at the mu-receptor, for the (+)-3a-f and the (-)-3a-f series. It is noteworthy that inversion of configuration at the nitrogen-bearing carbon atom [(5S,8S,9S)-8-amino-3-hydroxy-5,9-methano-9-(methoxymethyl)-5-methylbenzocyclooctene, (+)-3a vs (5S,8S,9R)-8-amino-3-hydroxy-5,9-methanoxymethyl)-5-methylbenzocyclooctene, (dl)-22] resulted in a >10-fold increase in kappa-receptor affinity. Antinociceptive studies demonstrated that (dl)-22 was a full kappa-agonist while (+)-3a and (-)-3a did not possess kappa-activity. Although both (dl)-22 and (+)-3a/(-)-3a had high affinity for the mu-receptor, these compounds did not act as high-affinity agonists or antagonists at this receptor.

  DOI：

  10.1021/jm950817g

文献信息

• Asymmetric Syntheses, Opioid Receptor Affinities, and Antinociceptive Effects of 8-Amino-5,9-methanobenzocyclooctenes, a New Class of Structural Analogues of the Morphine Alkaloids
  作者：Arthur G. Schultz、Aihua Wang、Carlos Alva、Alice Sebastian、Stanley D. Glick、Darlene C. Deecher、Jean M. Bidlack

  DOI：10.1021/jm950817g

  日期：1996.1.1

  Several 8-amino-5,9-methanobenzocyclooctenes have been prepared by asymmetric organic synthesis techniques. Opioid receptor affinity studies have revealed the virtual absence of enantioselectivity for receptor binding, particularly at the mu-receptor, for the (+)-3a-f and the (-)-3a-f series. It is noteworthy that inversion of configuration at the nitrogen-bearing carbon atom [(5S,8S,9S)-8-amino-3-hydroxy-5,9-methano-9-(methoxymethyl)-5-methylbenzocyclooctene, (+)-3a vs (5S,8S,9R)-8-amino-3-hydroxy-5,9-methanoxymethyl)-5-methylbenzocyclooctene, (dl)-22] resulted in a >10-fold increase in kappa-receptor affinity. Antinociceptive studies demonstrated that (dl)-22 was a full kappa-agonist while (+)-3a and (-)-3a did not possess kappa-activity. Although both (dl)-22 and (+)-3a/(-)-3a had high affinity for the mu-receptor, these compounds did not act as high-affinity agonists or antagonists at this receptor.