ROD185

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: ROD185
• 英文别名: benzyl (1R)-1-[(2R)-5-oxooxolan-2-yl]-3,4-dihydro-1H-isoquinoline-2-carboxylate
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: FVDMDGICJYHMRB-UYAOXDASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5R,1R)-5-(2-benzyloxycarbonyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-dihydro-2(5H)-furanone 在 甲醇 、 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 ROD185
  参考文献：
  名称：

  Use of bicuculline, a GABA antagonist, as a template for the development of a new class of ligands showing positive allosteric modulation of the GABAA receptor

  摘要：

  Analogues of bicuculline devoid of the benzo ring fused to the lactone moiety were prepared by reacting 2-(tert-butyldimethylsiloxy)furans with 3,4-dihydroisoquinolinium salts. Some of these compounds (e.g., ROD185, 8) acted as modulators of the GABA(A) receptor, displacing ligands of the benzodiazepine binding site. They also strongly stimulated GABA currents mediated by recombinant GABA(A) receptors expressed in Xenopus oocytes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00514-x

文献信息

• 1-(BUTYROLACTONE)-ISOQUINOLINES N-SUBSTITUEES POUR LE TRAITEMENT DES TROUBLES NERVEUX
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：EP1224182B1

  公开（公告）日：2003-07-16
• US6649626B1
  申请人：——

  公开号：US6649626B1

  公开（公告）日：2003-11-18
• Use of bicuculline, a GABA antagonist, as a template for the development of a new class of ligands showing positive allosteric modulation of the GABAA receptor
  作者：Rodolphe Razet、Urs Thomet、Roman Furtmüller、Frantisek Jursky、Erwin Sigel、Werner Sieghart、Robert H Dodd

  DOI：10.1016/s0960-894x(00)00514-x

  日期：2000.11

  Analogues of bicuculline devoid of the benzo ring fused to the lactone moiety were prepared by reacting 2-(tert-butyldimethylsiloxy)furans with 3,4-dihydroisoquinolinium salts. Some of these compounds (e.g., ROD185, 8) acted as modulators of the GABA(A) receptor, displacing ligands of the benzodiazepine binding site. They also strongly stimulated GABA currents mediated by recombinant GABA(A) receptors expressed in Xenopus oocytes. (C) 2000 Elsevier Science Ltd. All rights reserved.