(3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-decahydro-isoquinoline-3-carboxylic acid | 503176-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-decahydro-isoquinoline-3-carboxylic acid
• 英文别名: (3S,4aR,6S,8aR)-6-[2-(2H-tetrazol-5-yl)anilino]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid
• CAS: 503176-97-4
• 化学式: C₁₇H₂₂N₆O₂
• 分子量: 342.401
• InChiKey: SPIBJDVGRFDGQS-OXIQGZBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-decahydro-isoquinoline-3-carboxylic acid 、 2-乙基-1-丁醇 在 盐酸 作用下， 以87%的产率得到2-ethylbutyl (3S,4aR,6S,8aR)-6-[2-(1H-tetrazol-5-yl)phenylamino]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic ester dihydrochloride
  参考文献：
  名称：

  Two Prodrugs of Potent and Selective GluR5 Kainate Receptor Antagonists Actives in Three Animal Models of Pain

  摘要：

  Amino acids 5 and 7, two potent and selective competitive GluR5 KA receptor antagonists, exhibited high GluR5 receptor affinity over other glutamate receptors. Their ester prodrugs 6 and 8 were orally active in three models of pain: reversal of formalin-induced paw licking, carrageenan-induced thermal hyperalgesia, and capsaicin-induced mechanical hyperalgesia.

  DOI：

  10.1021/jm0491952
• 作为产物：
  描述：

  ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate 在 盐酸 、 三正丁基叠氮化锡 作用下， 反应 144.0h， 生成 (3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-decahydro-isoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Two Prodrugs of Potent and Selective GluR5 Kainate Receptor Antagonists Actives in Three Animal Models of Pain

  摘要：

  Amino acids 5 and 7, two potent and selective competitive GluR5 KA receptor antagonists, exhibited high GluR5 receptor affinity over other glutamate receptors. Their ester prodrugs 6 and 8 were orally active in three models of pain: reversal of formalin-induced paw licking, carrageenan-induced thermal hyperalgesia, and capsaicin-induced mechanical hyperalgesia.

  DOI：

  10.1021/jm0491952

文献信息

• Two Prodrugs of Potent and Selective GluR5 Kainate Receptor Antagonists Actives in Three Animal Models of Pain
  作者：Esteban Dominguez、Smriti Iyengar、Harlan E. Shannon、David Bleakman、Andrew Alt、Brian M. Arnold、Michael G. Bell、Thomas J. Bleisch、Jennifer L. Buckmaster、Ana M. Castano、Miriam Del Prado、Ana Escribano、Sandra A. Filla、Ken H. Ho、Kevin J. Hudziak、Carrie K. Jones、Jose A. Martinez-Perez、Ana Mateo、Brian M. Mathes、Edward L. Mattiuz、Ann Marie L. Ogden、Rosa Maria A. Simmons、Douglas R. Stack、Robert E. Stratford、Mark A. Winter、Zhipei Wu、Paul L. Ornstein

  DOI：10.1021/jm0491952

  日期：2005.6.1

  Amino acids 5 and 7, two potent and selective competitive GluR5 KA receptor antagonists, exhibited high GluR5 receptor affinity over other glutamate receptors. Their ester prodrugs 6 and 8 were orally active in three models of pain: reversal of formalin-induced paw licking, carrageenan-induced thermal hyperalgesia, and capsaicin-induced mechanical hyperalgesia.