1-phenyl-4,5-dihydro-1H-imidazol-2-amine | 41213-54-1

• 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-phenyl-4,5-dihydro-1H-imidazol-2-amine
• 英文别名: 2-Amino-1-phenyl-imidazolin-2；1-phenyl-4,5-dihydro-1H-imidazol-2-ylamine；1-phenyl-4,5-dihydroimidazol-2-amine
• CAS: 41213-54-1
• 化学式: C₉H₁₁N₃
• mdl: MFCD01037244
• 分子量: 161.206
• InChiKey: DILMDBKVKPVPRX-UHFFFAOYSA-N

物化性质

• 沸点：
  291.2±23.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenyl-4,5-dihydro-1H-imidazol-2-amine 在 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 6.0h， 生成 5-oxo-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitrile
  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
• 作为产物：
  描述：

  1-phenyl-2-aminoimidazolinium bromide 在 sodium hydroxide 作用下， 生成 1-phenyl-4,5-dihydro-1H-imidazol-2-amine
  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

• Synthesis and structure-activity relationships of N,N'-di-o-tolylguanidine analogs, high-affinity ligands for the haloperidol-sensitive .sigma. receptor
  作者：Michael W. Scherz、Michelle Fialeix、James B. Fischer、N. Laxma Reddy、Alfred C. Server、Mark S. Sonders、Barbara C. Tester、Eckard Weber、Scott T. Wong、John F. W. Keana

  DOI：10.1021/jm00171a016

  日期：1990.9

  2-CH3C6H5). Replacement of one or both aryl rings with certain saturated carbocycles (e.g. cyclohexyl, norbornyl, or adamantyl) leads to a significant increase in affinity. By combining the best aromatic and best saturated carbocyclic substituents in the same molecule, we arrived at some of the most potent sigma ligands described to date (e.g. N-exo-2-norbornyl-N'-(2-iodophenyl)guanidine, IC50 = 3 nM vs [3H]-3)

  着眼于新型非典型抗精神病药的开发，我们研究了氟哌啶醇敏感的sigma受体的N，N'-二-邻甲苯基胍（DTG，3）及其同类物的结构亲和力关系。合成了许多DTG类似物，并在豚鼠脑膜匀浆的体外放射性配体置换实验中使用了高sigma特异性放射性配体[3H] -3和[3H]-（+）-3-（3-羟苯基）进行了评估。 -N-（1-丙基）哌啶和苯环利定（PCP）受体特异性化合物[3H] -N- [1-（2-噻吩基）-环己基]哌啶和[3H]-（+）-5-甲基-10 ，11-二氢-5H-二苯并[a，d]环庚烯-5，10-亚胺。N，N'-二芳基胍对sigma受体的亲和力随邻位取代基的体积比C2H5大而增加。疏水取代基通常优于类似位置的亲水取代基。此外，电子中性取代基优于强电子给体或吸电子基团。只要胍的至少一侧带有优选基团（例如2-CH 3 C 6 H 5），通常就可以保持与σ受体的显着结合。用某些饱和的碳环（例
• Bicyclic heterocycles as HIV-integrase inhibitors
  申请人：Banville Jacques

  公开号：US20070049606A1

  公开（公告）日：2007-03-01

  The invention encompasses a series cyclic bicyclic heterocyclic compounds of Formula I which are inhibitors of HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV.

  本发明涵盖了一系列公式I的环状双环杂环化合物，它们是HIV整合酶的抑制剂，可以防止病毒整合到人类DNA中。这种作用使得这些化合物在治疗HIV感染和艾滋病方面非常有用。本发明还涵盖了用于治疗HIV感染者的药物组合物和方法。
• Synthesis, central nervous system activity and structure–activity relationship of N-substituted derivatives of 1-arylimidazolidyn-2-ylideneurea and products of their cyclization
  作者：Elżbieta Szacoń、Marzena Rządkowska、Agnieszka A. Kaczor、Ewa Kędzierska、Antonina Mazur、Sylwia Fidecka、Dariusz Matosiuk

  DOI：10.3109/14756366.2014.965699

  日期：2015.9.3

  Both series of N-substituted derivatives of 1-arylimidazolidyn-2-ylideneureas were subjected to cyclization to respective imidazo[1,2-a][1,3,5]triazines. Chain and cyclic compounds bearing ester moiety affected spontaneous locomotor activity, body temperature of mice as well as showed antinociceptive and serotoninergic activity. Interestingly, their antinociceptive activity was not reversed by naloxone

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• Synthesis and pharmacological activity of new carbonyl derivatives of 1-aryl-2-iminoimidazolidine
  作者：Dariusz Matosiuk、Sylwia Fidecka、Lucyna Antkiewicz-Michaluk、Izabela Dybala、Anna E Koziol

  DOI：10.1016/s0223-5234(02)01407-1

  日期：2002.10

  mechanism of their analgesic and serotonergic activity was confirmed in the binding assay tests (by radioligand displacement) toward the opioid mu and serotonin 5-HT(2) receptors. Additionally, they exhibited affinity toward the benzodiazepine (BZD) receptor as well, although in behavioral tests compounds did not produce any clear depressive effect on the central nervous system (CNS) of mice. Simple chemical

  介绍了1-芳基-5,6（1H）二氧代-2,3-二氢咪唑并[1,2-a]咪唑（D）的合成及药理活性。通过与草酸衍生物-乙酯（2）或氯化物（3）的环化反应，从1-芳基-2-亚氨基咪唑烷（1）获得标题化合物。在动物和结合试验中测试了它们的药理活性。具有中等急性毒性（LD（50）约为200 mg kg（-1），ip），由于“扭体”和“热板”试验的结果，它们表现出显着的镇痛和血清素活性，并减少了“头部”数量服用5-HTP（5-羟色氨酸）后抽搐发作。小剂量的纳洛酮（5 mg kg（-1））使“扭体”试验中产生的抗伤害感受性逆转可以表明其镇痛活性类似于阿片类药物。他们对阿片类药物和5-羟色胺5-HT（2）受体的结合试验（通过放射性配体置换）证实了它们的镇痛和5-羟色胺活性可能是受抑制的。此外，尽管化合物在行为测试中并未对小鼠的中枢神经系统（CNS）产生明显的抑制作用，但它们对苯二氮卓（BZD）受体也具有
• Synthesis and pharmacological activity of new carbonyl derivatives of 1-aryl-2-iminoimidazolidine Part 1. Synthesis and pharmacological activity of chain derivatives of 1-aryl-2-iminoimidazolidine containing urea moiety
  作者：D Matosiuk

  DOI：10.1016/s0223-5234(01)01267-3

  日期：2001.10

  especially analgesic, activity on the animal central nervous system (CNS). They displayed substantial effect on the serotonine and catecholamine neurotransmission as well, at very low toxicity (LD(50) over 2000 mg kg(-1) i.p.). In the binding affinity tests they exhibited moderate affinity (on the micromolar level) toward opioid (mu) and serotonine (5HT(2)) receptors. The derivatives of series A had moderate

  介绍了1-芳基-2-亚氨基咪唑烷新羰基衍生物的合成及其理化性质。在1-芳基-2-亚氨基咪唑烷酮的缩合反应后，获得了异构体的1-（1-芳基咪唑烷-2-亚甲基）-3-芳基脲（A系列）和1-芳基-2-亚胺-3-芳基氨基羰基咪唑烷（B系列）。和芳基异氰酸酯。由各自的苯胺以两步反应合成了1-芳基-2-亚氨基咪唑烷。1-（1-苯基咪唑烷-2-亚甲基）-3-（4-氯苯基）脲（A2）的分子结构已经通过X射线晶体学测定。在行为动物试验中评估了两个研究系列的代表。它们对动物中枢神经系统（CNS）表现出显着的镇痛活性。他们还显示出对5-羟色胺和儿茶酚胺神经传递的实质性影响，而且毒性非常低（LD（50）超过2000 mg kg（-1）ip）。在结合亲和力测试中，他们对阿片样物质（μ）和血清素（5HT（2））受体表现出中等亲和力（在微摩尔水平）。A系列的衍生物对苯二氮卓（BZD）受体也具有中等亲和力。在它们的活性谱