2-氨基-5-甲基吲唑 | 1034874-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 2-氨基-5-甲基吲唑
• 英文名称: 2-amino-5-methylindazole
• 英文别名: 5-Methylindazol-2-amine；5-methylindazol-2-amine
• CAS: 1034874-92-4
• 化学式: C₈H₉N₃
• 分子量: 147.18
• InChiKey: ISNHYQFMKGJYBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氨基-5-甲基吲唑 、 2-thioxo-imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以61%的产率得到2-{[1,3-di(tert-butoxycarbonyl)imidazolidin-2-yl]imino}-5-methylindazole
  参考文献：
  名称：

  1-[(Imidazolidin-2-yl)imino]indazole. Highly α₂/I₁ Selective Agonist: Synthesis, X-ray Structure, and Biological Activity

  摘要：

  Novel benzazole derivatives bearing a (imidazolidin-2-yl)imino moiety at position I or 2 were synthesized by reacting 1-amino- or 2-aminobenzazoles with N,N'-bis(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of HgCl2. Structures of 1-[(imidazolidin-2-yl)imino]indazole (marsanidine, 13a) and free base of the 4-Cl derivative 12e were confirmed by X-ray single crystal structure analysis. Compound 13a was found to be the selective alpha(2)-adrenoceptor ligand with alpha(2)-adrenoceptor/imidazoline I-1 receptor selectivity ratio of 3879, while 1-[(imidazolidin-2-yl)imino]-7-methylindazole (13k) proved to be a mixed alpha(2)-adrenoceptor/imidazoline I-1 receptor agonist with alpha 2/I-1 selectivity ratio of 7.2. Compound 13k when administered intravenously to male Wistar rats induced a dose-dependent decrease in mean arterial blood pressure (ED50 = 0.6 mu g/kg) and heart rate, which was attenuated following pretreatment with alpha(2A)-adrenoceptor antagonist RX821002. Compound 13a may find a variety of medical uses ascribed to alpha(2)-adrenoceptor agonists, and its 7-methyl derivative 13k is a good candidate for development as a centrally acting antihypertensive drug.

  DOI：

  10.1021/jm800112s
• 作为产物：
  描述：

  5-甲基-1H-吲唑 在 sodium hydroxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 以23%的产率得到5-甲基-1H-吲唑-1-胺
  参考文献：
  名称：

  1-[(Imidazolidin-2-yl)imino]indazole. Highly α₂/I₁ Selective Agonist: Synthesis, X-ray Structure, and Biological Activity

  摘要：

  Novel benzazole derivatives bearing a (imidazolidin-2-yl)imino moiety at position I or 2 were synthesized by reacting 1-amino- or 2-aminobenzazoles with N,N'-bis(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of HgCl2. Structures of 1-[(imidazolidin-2-yl)imino]indazole (marsanidine, 13a) and free base of the 4-Cl derivative 12e were confirmed by X-ray single crystal structure analysis. Compound 13a was found to be the selective alpha(2)-adrenoceptor ligand with alpha(2)-adrenoceptor/imidazoline I-1 receptor selectivity ratio of 3879, while 1-[(imidazolidin-2-yl)imino]-7-methylindazole (13k) proved to be a mixed alpha(2)-adrenoceptor/imidazoline I-1 receptor agonist with alpha 2/I-1 selectivity ratio of 7.2. Compound 13k when administered intravenously to male Wistar rats induced a dose-dependent decrease in mean arterial blood pressure (ED50 = 0.6 mu g/kg) and heart rate, which was attenuated following pretreatment with alpha(2A)-adrenoceptor antagonist RX821002. Compound 13a may find a variety of medical uses ascribed to alpha(2)-adrenoceptor agonists, and its 7-methyl derivative 13k is a good candidate for development as a centrally acting antihypertensive drug.

  DOI：

  10.1021/jm800112s

文献信息

• 1-[(Imidazolidin-2-yl)imino]indazole. Highly α₂/I₁ Selective Agonist: Synthesis, X-ray Structure, and Biological Activity
  作者：Franciszek Sa̧czewski、Anita Kornicka、Apolonia Rybczyńska、Alan L. Hudson、Shu Sean Miao、Maria Gdaniec、Konrad Boblewski、Artur Lehmann

  DOI：10.1021/jm800112s

  日期：2008.6.1

  Novel benzazole derivatives bearing a (imidazolidin-2-yl)imino moiety at position I or 2 were synthesized by reacting 1-amino- or 2-aminobenzazoles with N,N'-bis(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of HgCl2. Structures of 1-[(imidazolidin-2-yl)imino]indazole (marsanidine, 13a) and free base of the 4-Cl derivative 12e were confirmed by X-ray single crystal structure analysis. Compound 13a was found to be the selective alpha(2)-adrenoceptor ligand with alpha(2)-adrenoceptor/imidazoline I-1 receptor selectivity ratio of 3879, while 1-[(imidazolidin-2-yl)imino]-7-methylindazole (13k) proved to be a mixed alpha(2)-adrenoceptor/imidazoline I-1 receptor agonist with alpha 2/I-1 selectivity ratio of 7.2. Compound 13k when administered intravenously to male Wistar rats induced a dose-dependent decrease in mean arterial blood pressure (ED50 = 0.6 mu g/kg) and heart rate, which was attenuated following pretreatment with alpha(2A)-adrenoceptor antagonist RX821002. Compound 13a may find a variety of medical uses ascribed to alpha(2)-adrenoceptor agonists, and its 7-methyl derivative 13k is a good candidate for development as a centrally acting antihypertensive drug.