(3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-octahydro-isoquinoline-2,3-dicarboxylic acid 3-ethyl ester 2-methyl ester | 503177-11-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-octahydro-isoquinoline-2,3-dicarboxylic acid 3-ethyl ester 2-methyl ester
• CAS: 503177-11-5
• 化学式: C₂₁H₂₈N₆O₄
• 分子量: 428.491
• InChiKey: VVPBVLSODUMMEH-KRXQYRFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  122.33
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-octahydro-isoquinoline-2,3-dicarboxylic acid 3-ethyl ester 2-methyl ester 在 盐酸 作用下， 反应 72.0h， 以0.060 g的产率得到(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
• 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 三正丁基叠氮化锡 作用下， 反应 72.0h， 生成 (3S,4aR,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenylamino]-octahydro-isoquinoline-2,3-dicarboxylic acid 3-ethyl ester 2-methyl ester
  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