2-(3-Methyl-5-nitro-imidazol-4-yl)sulfanylbenzoic acid

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(3-Methyl-5-nitro-imidazol-4-yl)sulfanylbenzoic acid
• 英文别名: 2-(3-methyl-5-nitroimidazol-4-yl)sulfanylbenzoic acid
• 化学式: C₁₁H₉N₃O₄S
• mdl: MFCD02679718
• 分子量: 279.276
• InChiKey: ISCZHKSKRHZFIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-Methyl-5-nitro-imidazol-4-yl)sulfanylbenzoic acid 、 5-(2-Aminoethyl)-[1,3]dioxolo[4,5-g]quinolin-8-one 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-N-(2-(8-oxo[1,3]dioxolo[4,5-g]quinolin-5(8H)-yl)ethyl)benzamide
  参考文献：
  名称：

  COMPOUNDS AND METHOD FOR TREATING HIV INFECTION

  摘要：

  Disclosed is a compound of formula (I) or salt thereof: Formula (I) for treating or preventing a human immunodeficiency virus (HIV) infection in a mammal, for inhibiting or preventing maturation of an immature human immunodeficiency virus (HIV) to a mature HIV, and for preventing or inhibiting a human immunodeficiency virus (HIV) infection in a mammal having at least one HIV viral particle on a surface thereof.

  公开号：

  WO2024151425A1
• 作为产物：
  描述：

  5-氯-1-甲基-4-硝基咪唑 、 硫代水杨酸 在 sodium hydroxide 作用下， 反应 1.0h， 以60%的产率得到2-(3-Methyl-5-nitro-imidazol-4-yl)sulfanylbenzoic acid
  参考文献：
  名称：

  Rational Design of Novel Immunosuppressive Drugs:  Analogues of Azathioprine Lacking the 6-Mercaptopurine Substituent Retain or Have Enhanced Immunosuppressive Effects

  摘要：

  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.

  DOI：

  10.1021/jm960132w

文献信息

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

  DOI：——

  日期：——