S-[(6-formyl-1,3-benzodioxol-5-yl)] N,N-dimethylcarbamothioate | 1357912-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: S-[(6-formyl-1,3-benzodioxol-5-yl)] N,N-dimethylcarbamothioate
• CAS: 1357912-37-8
• 化学式: C₁₁H₁₁NO₄S
• 分子量: 253.279
• InChiKey: GYBREUBJAFOPEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-[(6-formyl-1,3-benzodioxol-5-yl)] N,N-dimethylcarbamothioate 在 苯酐 、 二正丁胺 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.5h， 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
• 作为产物：
  描述：

  1,3-苯并二氧戊环-5-基乙酸酯 在 四氯化锡 、 sodium hydride 作用下， 以 四氢呋喃 、 二苯醚 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 S-[(6-formyl-1,3-benzodioxol-5-yl)] N,N-dimethylcarbamothioate
  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.