(+/-)-trans-2,3-methylenedioxy-11-ethyl-6a,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline hydrochloride

• 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: (+/-)-trans-2,3-methylenedioxy-11-ethyl-6a,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline hydrochloride
• 英文别名: (1R,13S)-19-ethyl-5,7,11-trioxa-14-azapentacyclo[11.8.0.02,10.04,8.016,21]henicosa-2,4(8),9,16(21),17,19-hexaene;hydrochloride
• 化学式: C₁₉H₁₉NO₃*ClH
• 分子量: 345.826
• InChiKey: ALQZLABDEBKIGP-AEFICSSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  39.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-苯并二氧戊环-5-基乙酸酯 在 盐酸 、 苯酐 、 正丁基锂 、 硼烷四氢呋喃络合物 、 水 、 四氯化锡 、 二正丁胺 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 182.5h， 生成 (+/-)-trans-2,3-methylenedioxy-11-ethyl-6a,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline hydrochloride
  参考文献：
  名称：

  Analogues of doxanthrine reveal differences between the dopamine D1 receptor binding properties of chromanoisoquinolines and hexahydrobenzo[a]phenanthridines

  摘要：

  Efforts to develop selective agonists for dopamine D-1-like receptors led to the discovery of dihydrexidine and doxanthrine, two bioisosteric [beta-phenyldopamine-type full agonist ligands that display selectivity and potency at D-1-like receptors. We report herein an improved methodology for the synthesis of substituted chromanoisoquinolines (doxanthrine derivatives) and the evaluation of several new compounds for their ability to bind to D-1- and D-2-like receptors. Identical pendant phenyl ring substitutions on the dihydrexidine and doxanthrine templates surprisingly led to different effects on D-1-like receptor binding, suggesting important differences between the interactions of these ligands with the D-1 receptor. We propose, based on the biological results and molecular modeling studies, that slight conformational differences between the tetralin and chroman-based compounds lead to a shift in the location of the pendant ring substituents within the receptor. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.039