4-methyl-N-[1-(3-nitro-1H-1,2,4-triazol-1-yl)-3-phenylpropan-2-yl]benzene-1-sulfonamide

• 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: 4-methyl-N-[1-(3-nitro-1H-1,2,4-triazol-1-yl)-3-phenylpropan-2-yl]benzene-1-sulfonamide
• 英文别名: 4-methyl-N-[1-(3-nitro-1,2,4-triazol-1-yl)-3-phenylpropan-2-yl]benzenesulfonamide
• 化学式: C₁₈H₁₉N₅O₄S
• 分子量: 401.446
• InChiKey: AFGUOEGQVXDRJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  S)-(+)- 2-苄基- 1-（对甲苯磺酰）氮丙啶 、 3-硝基-1,2,4-三氮唑 在 sodium hydride 作用下， 以 丙醇 为溶剂， 反应 6.0h， 以36%的产率得到4-methyl-N-[1-(3-nitro-1H-1,2,4-triazol-1-yl)-3-phenylpropan-2-yl]benzene-1-sulfonamide
  参考文献：
  名称：

  Novel 3-Nitrotriazole-Based Amides and Carbinols as Bifunctional Antichagasic Agents

  摘要：

  3-Nitro-1H-1,2,4-triazole-based amides with a linear, rigid core and 3-nitrotriazole-based fluconazole analogues were synthesized as dual functioning antitrypanosomal agents. Such compounds are excellent substrates for type I nitroreductase (NTR) located in the mitochondrion of trypanosomatids and, at the same time, act as inhibitors of the sterol 14a-demethylase (T. cruzi CYP51) enzyme. Because combination treatments against parasites are often superior to monotherapy, we believe that this emerging class of bifunctional compounds may introduce a new generation of antitrypanosomal drugs. In the present work, the synthesis and in vitro and in vivo evaluation of such compounds is discussed.

  DOI：

  10.1021/jm5015742

文献信息

• Novel 3-Nitrotriazole-Based Amides and Carbinols as Bifunctional Antichagasic Agents
  作者：Maria V. Papadopoulou、William D. Bloomer、Galina I. Lepesheva、Howard S. Rosenzweig、Marcel Kaiser、Benjamín Aguilera-Venegas、Shane R. Wilkinson、Eric Chatelain、Jean-Robert Ioset

  DOI：10.1021/jm5015742

  日期：2015.2.12

  3-Nitro-1H-1,2,4-triazole-based amides with a linear, rigid core and 3-nitrotriazole-based fluconazole analogues were synthesized as dual functioning antitrypanosomal agents. Such compounds are excellent substrates for type I nitroreductase (NTR) located in the mitochondrion of trypanosomatids and, at the same time, act as inhibitors of the sterol 14a-demethylase (T. cruzi CYP51) enzyme. Because combination treatments against parasites are often superior to monotherapy, we believe that this emerging class of bifunctional compounds may introduce a new generation of antitrypanosomal drugs. In the present work, the synthesis and in vitro and in vivo evaluation of such compounds is discussed.