1-(2-methoxyphenyl)-4,5-dihydro-1H-imidazol-2-amine | 174077-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-methoxyphenyl)-4,5-dihydro-1H-imidazol-2-amine
• 英文别名: 1-(2-methoxyphenyl)-4,5-dihydroimidazol-2-amine
• CAS: 174077-67-9
• 化学式: C₁₀H₁₃N₃O
• 分子量: 191.233
• InChiKey: JTMASTRJQWXJND-UHFFFAOYSA-N

物化性质

• 沸点：
  335.1±44.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-methoxyphenyl)-4,5-dihydro-1H-imidazol-2-amine 以 异丙醇 为溶剂， 反应 2.0h， 生成 ethyl 5-imino-1-(2-methoxyphenyl)-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  The pseudo-Michael reaction of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl ethoxymethylenecyanoacetate

  摘要：

  The pseudo-Michael reaction of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl 2-cyano-3-methoxyprop-2-enoate (ethyl ethoxymethylenecyanoacetate) is investigated. At -10 A degrees C reaction takes place on the exocyclic nitrogen atom, giving exclusively ethyl esters of 2-cyano-3-[(1-phenyl-4,5-dihydro-1H-imidazol-2-yl)amino]prop-2-enoic acid. The formation of isomeric enamines which may be a theoretical product of the reaction on N3 ring nitrogen atom is not observed. The N6 enamines, heated in boiling acetic acid, yield cyclic 1-aryl-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles. Heating of the enamines to the temperature of 120-140 A degrees C without a solvent makes it possible to obtain a mixture of 1-aryl-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles and ethyl 1-aryl-5-imino-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carboxylates. The reaction of the respective hydrobromides of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl ethoxymethylenecyanoacetate in the presence of triethylamine gives selectively 1-aryl-5-oxo-1,2,3,5-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles.

  DOI：

  10.1007/s00706-013-0982-y

文献信息

• Modulation of the MOP Receptor (μ Opioid Receptor) by Imidazo[1,2-a]imidazole-5,6-Diones: In Search of the Elucidation of the Mechanism of Action
  作者：Dominik Straszak、Agata Siwek、Monika Głuch-Lutwin、Barbara Mordyl、Marcin Kołaczkowski、Aldona Pietrzak、Mansur Rahnama-Hezavah、Bartłomiej Drop、Dariusz Matosiuk

  DOI：10.3390/molecules27092930

  日期：——

  allosteric centers of the receptors exhibit large structural diversity within particular types and even subtypes. Currently, a considerable interest is aroused by the modulation of μ-opioid receptors. The application of such a technique may result in a reduction in the dose or even discontinuation of classical opiates, thus eliminating the side effects typical of this class of drugs. Our aim is to obtain

  μ-阿片受体属于 G 蛋白偶联受体 (GPCR) 家族，它们的激活会触发一系列细胞内中继，最终达到镇痛效果。这种受体的经典激动剂，例如吗啡，是治疗急性和慢性疼痛的主要目标。然而，危险的副作用，如呼吸抑制或成瘾，显着限制了它们的广泛使用。受体的变构中心在特定类型甚至亚型中表现出很大的结构多样性。目前，μ-阿片受体的调节引起了相当大的兴趣。这种技术的应用可能会导致经典阿片类药物的剂量减少甚至停药，从而消除这类药物的典型副作用。H )二氧代-2,3-二氢咪唑[1,2- a]咪唑衍生物，并提供有关它们对 OP3（MOP，人 mu 阿片受体）的活性和选择性的更多信息。该研究基于以下观察结果：1-芳基-2-氨基咪唑啉的一些羰基衍生物在亚阈值剂量下与吗啡或 DAMGO 有很强的协同作用，产生与正常活性剂量相似的结果。为了阐明这种增强的可能机制，我们对具有 OP3 受体表达的 CHO-K1 细胞进行了一些体外功能测试（涉及
• Rza̧dkowska, Marzena; Szacoń, Elzbieta; Matosiuk, Dariusz, Acta poloniae pharmaceutica, 2012, vol. 69, # 6, p. 1270 - 1275
  作者：Rza̧dkowska, Marzena、Szacoń, Elzbieta、Matosiuk, Dariusz、Kȩdzierska, Ewa、Fidecka, Sylwia

  DOI：——

  日期：——
• Synthesis, antiviral activity and structure–activity relationship of 1-(1-aryl-4,5-dihydro-1<i>H</i>-imidazoline)-3-chlorosulfonylureas and products of their cyclization
  作者：Marzena Rządkowska、Elżbieta Szacoń、Agnieszka A. Kaczor、Barbara Rajtar、Łukasz Świątek、Małgorzata Polz-Dacewicz、Dariusz Matosiuk

  DOI：10.3109/14756366.2015.1069287

  日期：2016.9.2

  Novel 1-(1-aryl-4,5dihydro-1H-imidazoline)-3-chlorosulfonylourea derivatives 3a-3f were synthesized in the reaction of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with chlorosulfonyl isocyanate. The second series of compounds 4a-4f was prepared from the respective 1-(1-aryl-4,5-dihydro-1H-imidazoline)-3-chlorsulfonylureas 3a-3f and 1,1'-carbonyldiimidazole (CDI). The selected compounds were tested for their activity against Herpes simplex virus and coxsackievirus B3 (CVB3). It was determined that three derivatives, i.e 3d, 4a and 4d are active against Herpes simplex virus (HSV-1). Compounds 3d and 4c are active against CVB3. Their favorable activity can be primarily attributed to their low lipophilicity values. Moreover, the lack of substituent in the phenyl moiety or 4-methoxy substitution can be considered as the most beneficial for the antiviral activity.
• Rzadkowska; Tkaczynski, Pharmazie, <hi>1995</hi>, vol. 50, # 12, p. 822 - 822
  作者：Rzadkowska、Tkaczynski

  DOI：——

  日期：——
• MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO
  申请人：Dow Agrosciences LLC

  公开号：EP3347341B1

  公开（公告）日：2021-04-28