4-amino-2-ethyl-2H-1,2,3-triazole | 802915-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: 4-amino-2-ethyl-2H-1,2,3-triazole
• 英文别名: 2-ethyl-2H-1,2,3-triazol-4-amine；2-ethyltriazol-4-amine
• CAS: 802915-22-6
• 化学式: C₄H₈N₄
• mdl: MFCD09055264
• 分子量: 112.134
• InChiKey: VFHNHXVFSOEFFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1-(benzofuran-3-carbonyl)-4-(3-ethyl-1-methyl-1H-pyrazole-5-carboxamido)pyrrolidine-2-carboxylic acid 、 4-amino-2-ethyl-2H-1,2,3-triazole 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， 以55.6%的产率得到N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-((2-ethyl-2H-1,2,3-triazol-4-yl)carbamoyl)pyrrolidin-3-yl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Encoded Library Technology as a Source of Hits for the Discovery and Lead Optimization of a Potent and Selective Class of Bactericidal Direct Inhibitors of Mycobacterium tuberculosis InhA

  摘要：

  Tuberculosis (TB) is one of the world's oldest and deadliest diseases, killing a person every 20 s. InhA, the enoyl-ACP reductase from Mycobacterium tuberculosis, is the target of the frontline antitubercular drug isoniazid (INH). Compounds that directly target InhA and do not require activation by mycobacterial catalase peroxidase KatG are promising candidates for treating infections caused by INH resistant strains. The application of the encoded library technology (ELT) to the discovery of direct InhA inhibitors yielded compound 7 endowed with good enzymatic potency but with low antitubercular potency. This work reports the hit identification, the selected strategy for potency optimization, the structure-activity relationships of a hundred analogues synthesized, and the results of the in vivo efficacy studies performed with the lead compound 65.

  DOI：

  10.1021/jm401326j
• 作为产物：
  描述：

  2-ethyl-4-nitro-2H-1,2,3-triazole 在 1% Pd/C 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以92%的产率得到4-amino-2-ethyl-2H-1,2,3-triazole
  参考文献：
  名称：

  HETEROARYLOXY QUINAZOLINE DERIVATIVE

  摘要：

  公开号：

  EP2221301B1

文献信息

• Trifluoromethyl Sulfones and Perfluoroalkanesulfonamides of the Azole Series
  作者：V. I. Meshcheryakov、B. A. Shainyan

  DOI：10.1023/b:rujo.0000034977.74026.b3

  日期：2004.3

  2-Phenyl-4-trifluoromethylsulfonylmethyl-2H-1,2,3-triazole was synthesized from 4-bromomethyl-2-phenyl-2H- 1,2,3-triazole and sodium trifluoromethanesulfinate CF3SO2Na. 1(2)-Ethyl-4-nitro-1 (2)H-1,2,3-triazoles and 4-nitro-2-phenyl-2H-1,2,3-triazole were reduced to the corresponding amines. Intermediate 1,2-bis(1-ethyl-1H-1,2,3-triazol-4-yl)diazene 1-oxide exists as a mixture of syn and anti isomers, the former being stabilized via formation of a strong intramolecular hydrogen bond. The reduction of 2-ethyl-4-nitro-2H-1,2,3-triazole in the presence of HCl afforded the target 4-amino-2-ethyl-2H-1,2,3-triazole and also 4-amino-5chloro-2-ethyl-2H-1,2,3-triazole. Treatment of alkyl-substituted 4-amino-1.2,3-triazoles with trifluoromethanesulfonyl chloride and pentafluoroethanesulfon I chloride gave N-triazolyl-substituted trifluoromethane- and pentafluoroethanesulfonamides and -imides.