ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenoxy)-2-(tert-butoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate | 503292-41-9

• 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-cyanophenoxy)-2-(tert-butoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate
• 英文别名: 2-O-tert-butyl 3-O-ethyl (3S,4aS,6S,8aR)-6-(2-cyanophenoxy)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-2,3-dicarboxylate
• CAS: 503292-41-9
• 化学式: C₂₄H₃₂N₂O₅
• 分子量: 428.528
• InChiKey: CQZYSRAKMQAJRZ-YRPNKDGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  88.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenoxy)-2-(tert-butoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate 在 盐酸 、 lithium hydroxide 、 三正丁基叠氮化锡 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 72.0h， 生成 (3S,4aS,6S,8aR)-6-[2-(1H-Tetrazol-5-yl)-phenoxy]-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,8aR)-6-oxo-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate 在 吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 碘代三甲硅烷 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 ethyl (3S,4aR,6S,8aR)-6-(2-cyanophenoxy)-2-(tert-butoxycarbonyl)-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

• 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.