N,N-diethyl-10H-phenothiazine-10-carboxamide | 20828-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: N,N-diethyl-10H-phenothiazine-10-carboxamide
• 英文别名: phenothiazine-10-carboxylic acid diethylamide；Phenothiazin-10-carbonsaeure-diaethylamid；N,N-diethyl-phenothiazine-10-carboxamide；N,N-diethylphenothiazine-10-carboxamide
• CAS: 20828-88-0
• 化学式: C₁₇H₁₈N₂OS
• 分子量: 298.409
• InChiKey: VZWXJPGNJLOWRM-UHFFFAOYSA-N

物化性质

• 溶解度：
  2.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-10H-phenothiazine-10-carboxamide 、 间苯二甲醚 在 4-二甲氨基吡啶 、 三氟甲磺酸酐 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 51.1h， 以63%的产率得到N,N-diethyl-2,4-dimethoxybenzamide
  参考文献：
  名称：

  Direct synthesis of arenecarboxamides through Friedel–Crafts acylation using ureas

  摘要：

  The reaction of urea derivatives that contain the phenothiazine unit with trifluoromethanesulfonic anhydride in the presence of electron-rich aromatic compounds leads to the formation of arenecarboxamides. The reaction has been successfully demonstrated for several inter- and intramolecular systems. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.056
• 作为产物：
  描述：

  吩噻嗪-10-碳酰氯 、 二乙胺 生成 N,N-diethyl-10H-phenothiazine-10-carboxamide
  参考文献：
  名称：

  Dahlbom, Acta Chemica Scandinavica (1947), 1953, vol. 7, p. 885,887

  摘要：

  DOI：

文献信息

• Differential binding of phenothiazine urea derivatives to wild-type human cholinesterases and butyrylcholinesterase mutants
  作者：Sultan Darvesh、Ian R. Pottie、Katherine V. Darvesh、Robert S. McDonald、Ryan Walsh、Sarah Conrad、Andrea Penwell、Diane Mataija、Earl Martin

  DOI：10.1016/j.bmc.2010.01.066

  日期：2010.3

  A series of N-10 urea derivatives of phenothiazine was synthesized and each compound was evaluated for its ability to inhibit human cholinesterases. Most were specific inhibitors of BuChE. However, the potent inhibitory effects on both cholinesterases of one sub-class, the cationic aminoureas, provide an additional binding mechanism to cholinesterases for these compounds. The comparative effects of aminoureas on wild-type BuChE and several BuChE mutants indicate a binding process involving salt linkage with the aspartate of the cholinesterase peripheral anionic site. The effect of such compounds on cholinesterase activity at high substrate concentration supports ionic interaction of aminoureas at the peripheral anionic site. (C) 2010 Elsevier Ltd. All rights reserved.
• US4833138A
  申请人：——

  公开号：US4833138A

  公开（公告）日：1989-05-23
• Dahlbom, Acta Chemica Scandinavica (1947), 1953, vol. 7, p. 885,887
  作者：Dahlbom

  DOI：——

  日期：——
• Direct synthesis of arenecarboxamides through Friedel–Crafts acylation using ureas
  作者：Wenjiang Ying、Lalith S.R. Gamage、Luke R. Lovro、James W. Herndon、Nathan W. Jenkins、James W. Herndon

  DOI：10.1016/j.tetlet.2014.06.056

  日期：2014.8

  The reaction of urea derivatives that contain the phenothiazine unit with trifluoromethanesulfonic anhydride in the presence of electron-rich aromatic compounds leads to the formation of arenecarboxamides. The reaction has been successfully demonstrated for several inter- and intramolecular systems. (C) 2014 Elsevier Ltd. All rights reserved.