ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate | 503177-10-4

• 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: ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate
• 英文别名: Ethyl (3S, 4aR, 6S, 8aR) 6-(2-cyano-phenylamino)-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate；3-O-ethyl 2-O-methyl (3S,4aR,6S,8aR)-6-(2-cyanoanilino)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-2,3-dicarboxylate
• CAS: 503177-10-4
• 化学式: C₂₁H₂₇N₃O₄
• 分子量: 385.463
• InChiKey: CIQMUDLXEUCJNL-ZMMAXQRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 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,8aR)-6-oxo-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate 、 2-氨基苯甲腈 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 27.0h， 以32%的产率得到ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenylamino)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate
  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

• Excitatory amino acid receptor antagonists
  申请人：——

  公开号：US20040053961A1

  公开（公告）日：2004-03-18

  The present invention provides novel compounds of Formula (I), or the pharmaceutically acceptable salts or prodrugs thereof, and methods for treating neurological disorders and neurodegenerative diseases, particularly pain and migraine.

  本发明提供了式（I）的新化合物，或其药学上可接受的盐或前药，以及用于治疗神经系统疾病和神经退行性疾病的方法，特别是用于治疗疼痛和偏头痛。