N-[(3-{5-[(dimethylamino)methyl]-2-furyl}-1,2,4-triazol-5-yl)methyl]-N'-methyl-2-nitro-1,1-ethenediamine | 103851-87-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[(3-{5-[(dimethylamino)methyl]-2-furyl}-1,2,4-triazol-5-yl)methyl]-N'-methyl-2-nitro-1,1-ethenediamine
• 英文别名: (E)-1-N'-[[3-[5-[(dimethylamino)methyl]furan-2-yl]-1H-1,2,4-triazol-5-yl]methyl]-1-N-methyl-2-nitroethene-1,1-diamine
• CAS: 103851-87-2
• 化学式: C₁₃H₁₉N₇O₃
• 分子量: 321.339
• InChiKey: KDDCNZALJDSOPA-XYOKQWHBSA-N

物化性质

• 熔点：
  200-203 °C
• 沸点：
  536.7±60.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (E-)-N-methyl-1-(methylthio)-2-nitroethanamine 、 3-(aminomethyl)-5-<5-<(dimethylamino)methyl>-2-furyl>-1,2,4-triazole dihydrochloride 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 19.0h， 生成 N-[(3-{5-[(dimethylamino)methyl]-2-furyl}-1,2,4-triazol-5-yl)methyl]-N'-methyl-2-nitro-1,1-ethenediamine
  参考文献：
  名称：

  Bioisosteric prototype design of biaryl imidazolyl and triazolyl competitive histamine H2-receptor antagonists

  摘要：

  The structural relationship of the competitive histamine H2-receptor antagonist 3-amino-5-(2-amino-4-pyridyl)-1,2,4-triazole (1) to the agonist histamine and to antagonists of the cimetidine type was explored by the design and synthesis of four series of bioisosterically designed prototypes. Biological data from these series was best interpreted as indicating a similarity between the imidazole moiety of histamine and cimetidine and the 2-amino-4-pyridyl moiety of 1. On the basis of this data, sequential replacement of 2-amino-4-pyridyl by 2-[(dimethylamino)methyl]-5-furyl and 2-guanidino-4-triazolyl moieties led to a structurally more potent series of biaryl histamine H2-receptor antagonists. The best of these, 2-methyl-4-(2-guanidino-4-thiazolyl)imidazole (29, CP-57,361-1) was 120 times more potent as a histamine H2-receptor antagonist than 1.

  DOI：

  10.1021/jm00161a005

文献信息

• LIPINSKI C. A.; LAMATTINA J. L.; OATES P. J., J. MED. CHEM., 29,(1986) N 11, 2154-2163
  作者：LIPINSKI C. A.、 LAMATTINA J. L.、 OATES P. J.

  DOI：——

  日期：——
• Bioisosteric prototype design of biaryl imidazolyl and triazolyl competitive histamine H2-receptor antagonists
  作者：Christopher A. Lipinski、John L. LaMattina、P. J. Oates

  DOI：10.1021/jm00161a005

  日期：1986.11

  The structural relationship of the competitive histamine H2-receptor antagonist 3-amino-5-(2-amino-4-pyridyl)-1,2,4-triazole (1) to the agonist histamine and to antagonists of the cimetidine type was explored by the design and synthesis of four series of bioisosterically designed prototypes. Biological data from these series was best interpreted as indicating a similarity between the imidazole moiety of histamine and cimetidine and the 2-amino-4-pyridyl moiety of 1. On the basis of this data, sequential replacement of 2-amino-4-pyridyl by 2-[(dimethylamino)methyl]-5-furyl and 2-guanidino-4-triazolyl moieties led to a structurally more potent series of biaryl histamine H2-receptor antagonists. The best of these, 2-methyl-4-(2-guanidino-4-thiazolyl)imidazole (29, CP-57,361-1) was 120 times more potent as a histamine H2-receptor antagonist than 1.