1-[(imidazolidin-2-yl)imino]benzotriazole | 1034876-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-[(imidazolidin-2-yl)imino]benzotriazole
• 英文别名: 1-[(Imidazolidin-2-yl)imino]benzotriazole hydrochloride；N-(4,5-dihydro-1H-imidazol-2-yl)benzotriazol-1-amine
• CAS: 1034876-70-4
• 化学式: C₉H₁₀N₆
• 分子量: 202.219
• InChiKey: QUPCZTRXKRJORK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(imidazolidin-2-yl)imino]benzotriazole 在 盐酸 作用下， 以 甲醇 为溶剂， 以70%的产率得到1-[(imidazolidin-2-yl)imino]benzotriazole hydrochloride
  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：

  1-{[1,3-di(tert-butoxycarbonyl)imidazolidin-2-yl]imino}benzotriazole 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以65%的产率得到1-[(imidazolidin-2-yl)imino]benzotriazole
  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.