4-氯吲唑-1-胺 | 302944-57-6

• 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: 4-氯吲唑-1-胺
• 英文名称: 1-amino-4-chloroindazole
• 英文别名: 4-Chloro-indazol-1-ylamine；4-Chloro-1H-indazol-1-amine；4-chloroindazol-1-amine
• CAS: 302944-57-6
• 化学式: C₇H₆ClN₃
• 分子量: 167.598
• InChiKey: XHXIAGXESVZJAC-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  354.1±34.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-氯吲唑-1-胺 、 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36%的产率得到4-chloro-1-{[1,3-di(tert-butoxycarbonyl)imidazolidin-2-yl]imino}indazole
  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：

  4-氯-1H-吲唑 、 2,4,6-三甲基苯磺酰羟胺 以 四氢呋喃 、 水 、 mineral oil 为溶剂， 生成 4-氯吲唑-1-胺
  参考文献：
  名称：

  Herbicidal 3-(heterocycl-1-yl)-uracils

  摘要：

  本发明涉及一种新型的3-杂环-1-基尿嘧啉，其化学式为I：其中R1和R2与相邻的氮原子一起形成一个可选取代的、可选取代苯并的5元杂环环，R3到R5的含义如权利要求1所述。本发明还涉及一种生产这些物质的方法，以及含有这些化合物作为活性成分的除草剂组合物。

  公开号：

  US06376426B1

文献信息

• [EN] DERIVATIVES OF 1-[(IMIDAZOLIDIN-2-YL)IMINO)]INDAZOLE<br/>[FR] DÉRIVÉS DU 1-[(IMIDAZOLIDIN-2-YL)IMINO)]INDAZOLE
  申请人：IMP INNOVATIONS LTD

  公开号：WO2009071906A1

  公开（公告）日：2009-06-11

  The invention provides a compound of formula (I) wherein R1 denotes hydrogen, methyl or phenyl; R2, R3, R4 and R5 denote hydrogen, halogen, preferably a chlorine atom, alkyl, preferably methyl, alkoxyl, preferably methoxyl; m denotes a number 0 or 1; and HX denotes sulfuric, phosphoric, acetic, malonic, fumaric, oxalic, lactic, tartaric, citric, gluconic, p-toluenesulfonic, methanesulfonic acid, hydrogen bromide or hydrogen iodide, preferably hydrogen chloride. The use of the compounds as α2-adrenergic receptor agonists is also provided.

  本发明提供了一种式子为(I)的化合物，其中R1表示氢、甲基或苯基；R2、R3、R4和R5表示氢、卤素，优选为氯原子，烷基，优选为甲基，烷氧基，优选为甲氧基；m表示数字0或1；HX表示硫酸、磷酸、醋酸、马龙酸、富马酸、草酸、乳酸、酒石酸、柠檬酸、葡萄糖酸、对甲苯磺酸、甲磺酸、氢溴酸或氢碘酸，优选为氢氯酸。本发明还提供将该化合物用作α2肾上腺素受体激动剂的方法。
• DERIVATIVES OF 1-[(IMIDAZOLIDIN-2-YL)IMINO)]INDAZOLE
  申请人：Imperial Innovations Limited

  公开号：EP2227464A1

  公开（公告）日：2010-09-15
• US6376426B1
  申请人：——

  公开号：US6376426B1

  公开（公告）日：2002-04-23
• [EN] HERBICIDAL 3-(HETEROCYCL-1-YL)-URACILS<br/>[FR] 3-(HETEROCYCL-1-YL)-URACILES HERBICIDES
  申请人：AMERICAN CYANAMID CO

  公开号：WO2000064889A1

  公开（公告）日：2000-11-02

  The invention relates to novel 3-heteorcycl-1-yluracils of formula (I) wherein R?1 and R2¿ together with the interjacent nitrogen atom form an optionally substituted, optionally benzo-condensed 5-membered heterocyclic ring and R3 through R5 have the meaning given in claim 1. The invention also relates to a method of the production of these substances and to herbicidal compositions containing such compounds as active ingredients.
• 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.