1-Methyl-4-nitro-5-imidazolyl 2-Aminophenyl Sulfide | 53900-32-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-Methyl-4-nitro-5-imidazolyl 2-Aminophenyl Sulfide
• 英文别名: 1-methyl-4-nitro-5-(o-aminophenyl)mercaptoimidazole；2-(3-methyl-5-nitro-3H-imidazol-4-ylsulfanyl)-aniline；2-(3-methyl-5-nitro-3H-imidazol-4-ylmercapto)-aniline；2-(3-Methyl-5-nitro-3H-imidazol-4-ylmercapto)-anilin；Imidazole, 5-(O-aminophenylthio)-1-methyl-4-nitro-；2-(3-methyl-5-nitroimidazol-4-yl)sulfanylaniline
• CAS: 53900-32-6
• 化学式: C₁₀H₁₀N₄O₂S
• 分子量: 250.281
• InChiKey: QYHRABNYVGQVDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丁二酸酐 、 1-Methyl-4-nitro-5-imidazolyl 2-Aminophenyl Sulfide 以 苯 为溶剂， 反应 3.0h， 以69%的产率得到1-Methyl-4-nitro-5-imidazolyl 2-Succinamidophenyl Sulfide
  参考文献：
  名称：

  取代的芳基1-甲基-4-硝基-5-咪唑基砜的受控氧化合成

  摘要：

  由硫化物前体合成了带有半琥珀酰氨基侧基的芳基咪唑基砜，用于与生物聚合物的运输系统偶联。过氧化物影响的硫的氧化反应总是伴随着羧酰胺基团的裂解氧化为硝基官能团，该过程可以通过仔细控制反应条件而最小化。

  DOI：

  10.1002/jhet.5570230425
• 作为产物：
  描述：

  5-氯-1-甲基-4-硝基咪唑 、 2-氨基苯硫醇 以70%的产率得到1-Methyl-4-nitro-5-imidazolyl 2-Aminophenyl Sulfide
  参考文献：
  名称：

  取代的芳基1-甲基-4-硝基-5-咪唑基砜的受控氧化合成

  摘要：

  由硫化物前体合成了带有半琥珀酰氨基侧基的芳基咪唑基砜，用于与生物聚合物的运输系统偶联。过氧化物影响的硫的氧化反应总是伴随着羧酰胺基团的裂解氧化为硝基官能团，该过程可以通过仔细控制反应条件而最小化。

  DOI：

  10.1002/jhet.5570230425

文献信息

• 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.
• Arya, V.P.; Nagarajan, K.; Shenoy, S.J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, p. 1115 - 1117
  作者：Arya, V.P.、Nagarajan, K.、Shenoy, S.J.

  DOI：——

  日期：——
• MROCZKIEWICZ, A., ACTA POL. PHARM., 1981, 38, N 3, 379-382
  作者：MROCZKIEWICZ, A.

  DOI：——

  日期：——
• ARYA, V. P.;NAGARAJAN, K.;SHENOY, S. J., INDIAN J. CHEM., 1982, 21, N 12, 1115-1117
  作者：ARYA, V. P.、NAGARAJAN, K.、SHENOY, S. J.

  DOI：——

  日期：——
• A controlled-oxidation synthesis of substituted aryl 1-methyl-4-nitro-5-imidazolyl sulfones
  作者：Ned D. Heindel、C. Jeffrey Lacey、Roger Egolf、Belle N. Mease、Keith J. Schray

  DOI：10.1002/jhet.5570230425

  日期：1986.7

  Aryl imidazolyl sulfones bearing pendant hemisuccinamido groups for conjugation to biopolymer transport systems were synthesized from sulfide precursors. The peroxide-effected oxidation at sulfur was invariably accompanied by some cleavage-oxidation of the carboxamido groups to nitro functionalities, a process which could be minimized by careful control of the reaction conditions.

  由硫化物前体合成了带有半琥珀酰氨基侧基的芳基咪唑基砜，用于与生物聚合物的运输系统偶联。过氧化物影响的硫的氧化反应总是伴随着羧酰胺基团的裂解氧化为硝基官能团，该过程可以通过仔细控制反应条件而最小化。

表征谱图