7-Chloro-2-phenyl-1,2,3,10-tetrahydrophenothiazin-4-one | 89193-74-8

• 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: 7-Chloro-2-phenyl-1,2,3,10-tetrahydrophenothiazin-4-one
• CAS: 89193-74-8
• 化学式: C₁₈H₁₄ClNOS
• 分子量: 327.834
• InChiKey: MBZKWTIRQYBDQW-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  471.5±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-Chloro-2-phenyl-1,2,3,10-tetrahydrophenothiazin-4-one 在 双氧水 、 溶剂黄146 作用下， 反应 2.75h， 以71%的产率得到7-chloro-1,2-dihydro-2-phenyl-4(3H,10H)-phenothiazinone 5,5-dioxide
  参考文献：
  名称：

  Synthesis and Antimalarial Effects of Phenothiazine Inhibitors of a Plasmodium falciparum Cysteine Protease

  摘要：

  Acridinediones have previously been shown to have potent antimalarial activity. A series of sulfur isosteres of acridinediones Slave been synthesized and evaluated for their inhibition of the Plasmodium falciparum cysteine protease falcipain and for their antimalarial activity. A number of these phenothiazines inhibited falcipain and demonstrated activity against cultured P, falciparum parasites at low micromolar concentrations. Wie propose that the compounds exerted their antimalarial effects by two mechanisms, one of which involves the inhibition of falcipain and a consequent block in parasite degradation of hemoglobin. These compounds and related phenothiazines are worthy of further study as potential antimalarial agents.

  DOI：

  10.1021/jm970266p
• 作为产物：
  描述：

  2-氨基-5-氯噻吩 、 5-phenyl-cyclohexane-1,3-dione 以 二甲基亚砜 为溶剂， 反应 1.0h， 以70%的产率得到7-Chloro-2-phenyl-1,2,3,10-tetrahydrophenothiazin-4-one
  参考文献：
  名称：

  A Facile Synthesis of 2,3-Dihydro-1H-phenothiazin-4(10H)-ones

  摘要：

  DOI：

  10.1055/s-1983-30578

文献信息

• A Facile Synthesis of 2,3-Dihydro-1<i>H</i>-phenothiazin-4(10<i>H</i>)-ones
  作者：M. L. Jain、R. P. Soni

  DOI：10.1055/s-1983-30578

  日期：——
• JAIN, M. L.;SONI, R. P., SYNTHESIS, BRD, 1983, N 11, 933-935
  作者：JAIN, M. L.、SONI, R. P.

  DOI：——

  日期：——
• Synthesis and Antimalarial Effects of Phenothiazine Inhibitors of a <i>Plasmodium falciparum</i> Cysteine Protease
  作者：José N. Domínguez、Simón López、Jaime Charris、Lúcido Iarruso、Gricela Lobo、Andrey Semenov、Jed E. Olson、Philip J. Rosenthal

  DOI：10.1021/jm970266p

  日期：1997.8.1

  Acridinediones have previously been shown to have potent antimalarial activity. A series of sulfur isosteres of acridinediones Slave been synthesized and evaluated for their inhibition of the Plasmodium falciparum cysteine protease falcipain and for their antimalarial activity. A number of these phenothiazines inhibited falcipain and demonstrated activity against cultured P, falciparum parasites at low micromolar concentrations. Wie propose that the compounds exerted their antimalarial effects by two mechanisms, one of which involves the inhibition of falcipain and a consequent block in parasite degradation of hemoglobin. These compounds and related phenothiazines are worthy of further study as potential antimalarial agents.