N(4)-methyl-4-nitrobenzophenone thiosemicarbazone | 1075215-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N(4)-methyl-4-nitrobenzophenone thiosemicarbazone
• 英文别名: N4-methyl-4-nitrobenzophenone thiosemicarbazone；4-nitrobenzophenone N4-methylthiosemicarbazone；H4NO2Bz4M
• CAS: 1075215-16-5
• 化学式: C₁₅H₁₄N₄O₂S
• 分子量: 314.368
• InChiKey: LUYVPSWCGCDOPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  79.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  manganese(II) chloride tetrahydrate 、 N(4)-methyl-4-nitrobenzophenone thiosemicarbazone 以 乙醇 为溶剂， 以88%的产率得到dichlorobis(N(4)-methyl-4-nitrobenzophenone thiosemicarbazone)manganese(II)
  参考文献：
  名称：

  Manganese(II) complexes with N4-methyl-4-nitrobenzaldehyde, N4-methyl-4-nitroacetofenone, and N4-methyl-4-nitrobenzophenone thiosemicarbazone: Investigation of in vitro activity against Trypanosoma cruzi

  摘要：

  Thiosemicarbazones are known to be active against different pathogenic microorganisms including Trypanosoma cruzi, the etiological agent of Chagas disease. In the search for new therapeutic drugs against this illness, the complexes [Mn(H4NO(2)Fo4M)(2)Cl-2] (1), [Mn(H(4)NO(2)Ac4M)(2)Cl-2] (2) and [Mn(H4NO(2) Bz4M)(2)Cl-2] (3) of N-4-methyl-4-nitrobenzaldehyde thiosemicarbazone (H4NO(2)Fo4M), N-4-methyl-4-nitroacetophenone thiosemicarbazone (H4NO(2)Ac4M) and N-4-methyl-4-nitrobenzophenone thiosemicarbazone (H4NO(2)Bz4M) were obtained and screened in vitro against bloodstream and intracellular forms of T. cruzi. H4NO(2)Fo4M, H4NO(2)Ac4M and their Mn(II) complexes displayed poor effect on bloodstream trypomastigotes, with IC50 values ranging from 68 to >200 mu M. However, although H4NO(2)Bz4M was also not active, its corresponding Mn(II) complex presented high effect on this T. cruzi form, with an IC50 value of 19 mu M. The effect of complex (3), against trypomastigotes of T. cruzi supports further in vitro as well as in vivo studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.04.023
• 作为产物：
  描述：

  4-硝基二苯甲酮 、 4-甲基氨基硫脲 在 硫酸 作用下， 以 乙醇 为溶剂， 生成 N(4)-methyl-4-nitrobenzophenone thiosemicarbazone
  参考文献：
  名称：

  Manganese(II) complexes with N4-methyl-4-nitrobenzaldehyde, N4-methyl-4-nitroacetofenone, and N4-methyl-4-nitrobenzophenone thiosemicarbazone: Investigation of in vitro activity against Trypanosoma cruzi

  摘要：

  Thiosemicarbazones are known to be active against different pathogenic microorganisms including Trypanosoma cruzi, the etiological agent of Chagas disease. In the search for new therapeutic drugs against this illness, the complexes [Mn(H4NO(2)Fo4M)(2)Cl-2] (1), [Mn(H(4)NO(2)Ac4M)(2)Cl-2] (2) and [Mn(H4NO(2) Bz4M)(2)Cl-2] (3) of N-4-methyl-4-nitrobenzaldehyde thiosemicarbazone (H4NO(2)Fo4M), N-4-methyl-4-nitroacetophenone thiosemicarbazone (H4NO(2)Ac4M) and N-4-methyl-4-nitrobenzophenone thiosemicarbazone (H4NO(2)Bz4M) were obtained and screened in vitro against bloodstream and intracellular forms of T. cruzi. H4NO(2)Fo4M, H4NO(2)Ac4M and their Mn(II) complexes displayed poor effect on bloodstream trypomastigotes, with IC50 values ranging from 68 to >200 mu M. However, although H4NO(2)Bz4M was also not active, its corresponding Mn(II) complex presented high effect on this T. cruzi form, with an IC50 value of 19 mu M. The effect of complex (3), against trypomastigotes of T. cruzi supports further in vitro as well as in vivo studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.04.023

文献信息

• Spectral and electrochemical studies of ruthenium(II) complexes with N4-methyl-4-nitrobenzaldehyde and N4-methyl-4-nitrobenzophenone thiosemicarbazone: Potential anti-trypanosomal agents
  作者：Claudia Rodrigues、Alzir A. Batista、Ricardo Q. Aucélio、Letícia R. Teixeira、Lorenzo do Canto Visentin、Heloisa Beraldo

  DOI：10.1016/j.poly.2008.06.002

  日期：2008.9

  N-4-Methyl-4-nitrobenzaldehyde thiosemicarbazone (H4NO(2)Fo4M), N-4-methyl-4-nitrobenzophenone thiosemicarbazone (H4NO(2)Bz4M) and their ruthenium(II) complexes [Ru(4NO(2)Fo4M)(2)(PPh3)(2)] (1), [Ru(4NO(2)Bz4M)(2)(PPh3)(2)] (2), [Ru(4NO(2)Fo4M)(2)(dppb)] (3) and [Ru(4NO(2)Bz4M)(2)(dppb)] (4) (dppb = 1,4-bis(diphenylphospine)butane) were obtained and characterized. The crystal structure of H4NO(2)Fo4M has been determined. Electrochemical studies have shown that the nitro anion radical, one of the proposed intermediates in the mechanism of action of nitro-containing anti-trypanosomal drugs, is formed at approximately -1.00 V in the free thiosemicarbazones as well as in their corresponding ruthenium(II) complexes, suggesting their potential to act as antitrypanosomal drugs. The natural fluorescence of H4NO(2)Fo4M, H4NO(2)Bz4M and complexes (1)-(4) provides a way to identify and to monitor their concentration in biological systems. (C) 2008 Elsevier Ltd. All rights reserved.