N-[3-(3-nitro-1H-1,2,4-triazol-1-yl)propyl]-1,5-naphthyridin-4-amine hydrochloride | 1346453-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-[3-(3-nitro-1H-1,2,4-triazol-1-yl)propyl]-1,5-naphthyridin-4-amine hydrochloride
• 英文别名: N-[3-(3-nitro-1,2,4-triazol-1-yl)propyl]-1,5-naphthyridin-4-amine;hydrochloride
• CAS: 1346453-23-3
• 化学式: C₁₃H₁₃N₇O₂*ClH
• 分子量: 335.753
• InChiKey: MBFOHQAOIYGVJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氯-1,5-萘啶 、 3-(3-nitro-1H-1,2,4-triazol-1-yl)propan-1-amine 以 丙醇 为溶剂， 以50%的产率得到N-[3-(3-nitro-1H-1,2,4-triazol-1-yl)propyl]-1,5-naphthyridin-4-amine hydrochloride
  参考文献：
  名称：

  Novel 3-Nitro-1H-1,2,4-triazole-Based Aliphatic and Aromatic Amines as Anti-Chagasic Agents

  摘要：

  A series of novel 2-nitro-1H-imidazole- and 3-nitro-1H-1,2,4-triazole-based aromatic and aliphatic amines were screened for antitrypanosomal activity and mammalian cytotoxicity by the Drugs for Neglected Diseases initiative (DNDi). Out of 42 compounds tested, 18 3-nitro-1,2,4-triazoles and one 2-nitroimidazole displayed significant growth inhibitory properties against T. cruzi amastigotes (IC50 ranging from 40 nM to 1.97 mu M), without concomitant toxicity toward the host cells (L6 cells), having selectivity indices (SI) 44-1320. Most (16) of these active compounds were up to 33.8-fold more potent than the reference drug benznidazole, tested in parallel. Five novel 3-nitro-1,2,4-triazoles were active against bloodstream-form (BSF) T. b. rhodesiense trypomastigotes (IC50 at nM levels and SI 220-993). An NADH-dependent nitroreductase (TbNTR) plays a role in the antiparasitic activity because BSF T. b. brucei trypomastigotes with elevated TbNTR levels were hypersensitive to tested compounds. Therefore, a novel class of affordable 3-nitro-1,2,4-triazole-based compounds with antitrypanosomal activity has been identified.

  DOI：

  10.1021/jm201215n

文献信息

• Novel 3-Nitro-1<i>H</i>-1,2,4-triazole-Based Aliphatic and Aromatic Amines as Anti-Chagasic Agents
  作者：Maria V. Papadopoulou、Bernadette Bourdin Trunz、William D. Bloomer、Caroline McKenzie、Shane R. Wilkinson、Chaiya Prasittichai、Reto Brun、Marcel Kaiser、Els Torreele

  DOI：10.1021/jm201215n

  日期：2011.12.8

  A series of novel 2-nitro-1H-imidazole- and 3-nitro-1H-1,2,4-triazole-based aromatic and aliphatic amines were screened for antitrypanosomal activity and mammalian cytotoxicity by the Drugs for Neglected Diseases initiative (DNDi). Out of 42 compounds tested, 18 3-nitro-1,2,4-triazoles and one 2-nitroimidazole displayed significant growth inhibitory properties against T. cruzi amastigotes (IC50 ranging from 40 nM to 1.97 mu M), without concomitant toxicity toward the host cells (L6 cells), having selectivity indices (SI) 44-1320. Most (16) of these active compounds were up to 33.8-fold more potent than the reference drug benznidazole, tested in parallel. Five novel 3-nitro-1,2,4-triazoles were active against bloodstream-form (BSF) T. b. rhodesiense trypomastigotes (IC50 at nM levels and SI 220-993). An NADH-dependent nitroreductase (TbNTR) plays a role in the antiparasitic activity because BSF T. b. brucei trypomastigotes with elevated TbNTR levels were hypersensitive to tested compounds. Therefore, a novel class of affordable 3-nitro-1,2,4-triazole-based compounds with antitrypanosomal activity has been identified.