1-乙基-5-氯-2-甲基-4-硝基-1H-咪唑 | 2302-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-乙基-5-氯-2-甲基-4-硝基-1H-咪唑
• 英文名称: 1-ethyl-2-methyl-5-chloro-4-nitroimidazole
• 英文别名: 5-Chloro-1-ethyl-2-methyl-4-nitro-1H-imidazole；5-chloro-1-ethyl-2-methyl-4-nitroimidazole
• CAS: 2302-28-5
• 化学式: C₆H₈ClN₃O₂
• mdl: MFCD01928390
• 分子量: 189.601
• InChiKey: MVICIJDNZUMTFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙基-5-氯-2-甲基-4-硝基-1H-咪唑 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-azido-1-ethyl-2-methyl-4-nitro-1H-imidazole
  参考文献：
  名称：

  Synthesis of 2-aryl-2H,4H-imidazo[4,5-d][1,2,3]triazoles from triethyl N-(1-ethyl-2-methyl-4-nitro-1H-imidazol-5-yl)phosphorimidate by reaction with aryl isocyanates

  摘要：

  报告了一系列 2-芳基-2H,4H-咪唑并[4,5-d][1,2,3]三唑的合成。这些化合物是通过 N-(1-乙基-2-甲基-4-硝基-1H-咪唑-5-基)膦酰亚胺三乙酯与芳基异氰酸酯反应得到的，收率中等至良好。报告了 N-(1-乙基-2-甲基-4-硝基-1H-咪唑-5-基)膦酰亚胺三乙酯和 2-(4-三氟甲基苯基)取代的 2H,4H-咪唑并[4,5-d][1,2,3]三唑的 X 射线晶体结构。光谱证明了反应机理中提出的碳化二亚胺中间体。

  DOI：

  10.1039/b205216b
• 作为产物：
  描述：

  N,Nˊ-二乙基乙二酰胺 在 五氯化磷 、 硫酸 、 硝酸 、 三氯氧磷 作用下， 生成 1-乙基-5-氯-2-甲基-4-硝基-1H-咪唑
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1010383903327

文献信息

• Investigations in the imidazole series 97. Synthesis and some transformations of 5-nitro-5-hydroxyalkylamino- and 4-hydroxy-alkylamino-5-nitroimidazoles
  作者：P. M. Kochergin、L. A. Reznichenko、R. N. Gireva、E. V. Aleksandrova

  DOI：10.1007/bf02319492

  日期：1998.10
• Tennant, George; Wallis, Christopher J.; Weaver, George W., Journal of the Chemical Society. Perkin transactions I, 1999, # 7, p. 817 - 825
  作者：Tennant, George、Wallis, Christopher J.、Weaver, George W.

  DOI：——

  日期：——
• Tennant, George; Wallis, Christopher J.; Weaver, George W., Journal of the Chemical Society. Perkin transactions I, 1999, # 5, p. 629 - 640
  作者：Tennant, George、Wallis, Christopher J.、Weaver, George W.

  DOI：——

  日期：——
• Sarasin; Wegmann, Helvetica Chimica Acta, 1924, vol. 7, p. 714
  作者：Sarasin、Wegmann

  DOI：——

  日期：——
• Rational Design of Novel Immunosuppressive Drugs:  Analogues of Azathioprine Lacking the 6-Mercaptopurine Substituent Retain or Have Enhanced Immunosuppressive Effects
  作者：Duncan J. K. Crawford、John L. Maddocks、D. Neville Jones、Paul Szawlowski

  DOI：10.1021/jm960132w

  日期：1996.1.1

  Clinical use of the immunosuppressive drug azathioprine is limited by potentially serious toxic effects related to depression of bone marrow function. The immunosuppressive and toxic properties of azathioprine are regarded as being properties of the cytotoxicity of its metabolite, 6-mercaptopurine (6-MP). However, azathioprine has an immunosuppressive effect additional to that attributable to 6-MP alone, and we propose that this is associated with an action of the methylnitroimidazolyl substituent. This suggests a route to the rational design of nontoxic immunosuppressants by replacing the 6-MP component of azathioprine with nontoxic thiols. We have synthesized and tested in vitro 24 such analogues, with two being further tested in vivo. In the human mixed lymphocyte reaction, virtually all compounds showed some degree of activity, 10 compounds being more active than azathioprine. In vivo, two compounds were more effective than azathioprine at prolonging graft survival in mice. In an oral toxicity study in male CD1 mice at doses equivalent to those at which azathioprine caused severe bone marrow depression both analogues had no toxic effects. Our results show that the immunosuppressive effects and bone marrow toxicity of azathioprine are not a consequence of release of 6-MP alone, and with appropriate modification can be separated, an approach which may lead to less toxic immunosuppressive drugs.