(1R,9R,10R)-4-methoxy-1-methyl-10-[(4-methylphenyl)sulfonylamino]tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-9-carboxylic acid | 176959-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,9R,10R)-4-methoxy-1-methyl-10-[(4-methylphenyl)sulfonylamino]tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-9-carboxylic acid
• CAS: 176959-85-6
• 化学式: C₂₃H₂₇NO₅S
• 分子量: 429.537
• InChiKey: MCUMXLLNUVISBL-MZYLBHOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,9R,10R)-4-methoxy-1-methyl-10-[(4-methylphenyl)sulfonylamino]tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-9-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-[(1R,9R,10R)-9-(hydroxymethyl)-4-methoxy-1-methyl-10-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trienyl]-4-methylbenzenesulfonamide
  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：

  methyl (1R,9R,10R)-10-amino-4-methoxy-1-methyltricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-9-carboxylate 在 硫酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 62.0h， 生成 (1R,9R,10R)-4-methoxy-1-methyl-10-[(4-methylphenyl)sulfonylamino]tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-9-carboxylic acid
  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.