N-phenyl-10H-phenothiazine-10-carboxamide | 52893-45-5

• 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-phenyl-10H-phenothiazine-10-carboxamide
• 英文别名: phenothiazine-10-carboxylic acid anilide；Phenothiazin-10-carbonsaeure-anilid；N-phenylphenothiazine-10-carboxamide
• CAS: 52893-45-5
• 化学式: C₁₉H₁₄N₂OS
• 分子量: 318.399
• InChiKey: YNMBQQBSDFDHFH-UHFFFAOYSA-N

物化性质

• 熔点：
  189-190 °C
• 沸点：
  534.2±33.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenyl-10H-phenothiazine-10-carboxamide 、 苯胺 生成 2-ethanesulfonylmethyl-5-bromo-thiophene 、 1,1-二苯基脲
  参考文献：
  名称：

  Paschkowezky, Chemische Berichte, 1891, vol. 24, p. 2908

  摘要：

  DOI：
• 作为产物：
  描述：

  10-(N'-phenylchloroformimidoyl)phenothiazine 在 三乙胺 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 53.0h， 生成 N-phenyl-10H-phenothiazine-10-carboxamide
  参考文献：
  名称：

  Synthesis of 10-(N?-phenyl)imidoyl derivatives of phenothiazine, and their reactions with o,o-dialkylthio- and dithiophosphates

  摘要：

  DOI：

  10.1007/bf01168094

文献信息

• Design, synthesis, structure elucidation, antimicrobial, molecular docking, and SAR studies of novel urea derivatives bearing tricyclic aromatic hydrocarbon rings
  作者：Farid M. Sroor、Ahmed F. El‐Sayed、Mohamed Abdelraof

  DOI：10.1002/ardp.202300738

  日期：——

  The targeted compounds were prepared using both (9H-fluoren-9-ylidene)hydrazine (1) and 10H-phenothiazine (2) as starting materials. The treatment of 1 or 2 with different isocyanates afforded the title compounds 7a–d, 8a, and 8b in excellent yield. All compounds were characterized and ascertained by infrared, nuclear magnetic resonance, and elemental analyses as well as single-crystal X-ray diffraction

  使用(9 H-芴-9-亚基)肼( 1 )和10 H-吩噻嗪( 2 )作为起始原料制备目标化合物。用不同的异氰酸酯处理1或2，以优异的收率得到标题化合物7a-d 、 8a和8b 。所有化合物均通过红外、核磁共振、元素分析以及单晶 X 射线衍射进行了表征和确定。体外测试了所有化合物的抗菌效果，化合物7a 、 7b 、 8a和8b对枯草芽孢杆菌、金黄色葡萄球菌、铜绿假单胞菌、肺炎克雷伯菌和白色念珠菌均具有显着的抑制活性。此外，化合物7b和8b对所有细菌病原体的生物膜机制活性均具有强烈抑制作用，抑制率超过55%。分子对接模拟结果表明，化合物7a 、 7b 、 8a和8b表现出良好的结合能，并与甾醇 14-去甲基酶、二氢叶酸合酶、促旋酶 B、LasR（铜绿假单胞菌主要转录激活因子）的活性位点有效相互作用。 ) 和碳青霉烯酶分别用于白色念珠菌、金黄色葡萄球菌、枯草芽孢杆菌、肺炎克雷伯菌和铜绿假单胞菌。
• 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.
• Synthesis of 10-(N?-phenyl)imidoyl derivatives of phenothiazine, and their reactions with o,o-dialkylthio- and dithiophosphates
  作者：R. M. Kamalov、G. M. Makarov、D. Kh. Yarmukhametova、M. A. Pudovik、R. A. Cherkasov、A. N. Pudovik

  DOI：10.1007/bf01168094

  日期：1989.11
• Paschkowezky, Chemische Berichte, 1891, vol. 24, p. 2908
  作者：Paschkowezky

  DOI：——

  日期：——