3-nitro-2H-6,7-methylenedioxythiochromene | 1357912-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 3-nitro-2H-6,7-methylenedioxythiochromene
• 英文别名: 7-nitro-6H-thiopyrano[2,3-f][1,3]benzodioxole
• CAS: 1357912-38-9
• 化学式: C₁₀H₇NO₄S
• 分子量: 237.236
• InChiKey: KFMIWMXUFVSCMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-nitro-2H-6,7-methylenedioxythiochromene 在 magnesium 、 溶剂黄146 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 8.17h， 生成 (+/-)-trans-2,3-methylenedioxy-6a,12b-dihydro-6H-thiochromeno[3,4-c]isoquinoline
  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
• 作为产物：
  描述：

  1,3-苯并二氧戊环-5-基乙酸酯 在 苯酐 、 四氯化锡 、 sodium hydride 、 二正丁胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二苯醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.75h， 生成 3-nitro-2H-6,7-methylenedioxythiochromene
  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

文献信息

• Analogues of doxanthrine reveal differences between the dopamine D1 receptor binding properties of chromanoisoquinolines and hexahydrobenzo[a]phenanthridines
  作者：Juan Pablo Cueva、Benjamin R. Chemel、Jose I. Juncosa、Markus A. Lill、Val J. Watts、David E. Nichols

  DOI：10.1016/j.ejmech.2011.11.039

  日期：2012.2

  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.