4-(2-phenyl-1H-imidazol-1-yl)aniline | 850338-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2-phenyl-1H-imidazol-1-yl)aniline
• 英文别名: 4-(2-Phenylimidazol-1-yl)aniline
• CAS: 850338-87-3
• 化学式: C₁₅H₁₃N₃
• 分子量: 235.288
• InChiKey: DDIOWMZPRKZENF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• 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-(2-phenyl-1H-imidazol-1-yl)aniline 在 盐酸 、 sodium nitrite 、 磷酸 作用下， 反应 6.0h， 以65%的产率得到1,2-diphenylimidazole
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships at the GABA_A Receptor in Rat Brain, and Differential Electrophysiological Profile at the Recombinant Human GABA_A Receptor of a Series of Substituted 1,2-Diphenylimidazoles

  摘要：

  A series of new 1,2-diphenylimidazole derivatives (la-x) were synthesized and evaluated for their ability to potentiate gamma-aminobutyric acid (GABA)-evoked currents in Xenopus laevis oocytes expressing recombinant human GABAA receptors. Many of these compounds enhanced GABA action with potencies (EC50 = 0.19-19,mu M) and efficacies (maximal efficacies of up to 640%) similar to or greater than those of anesthetics such as etomidate, propofol, and alphaxalone. Structure- activity relationship analysis revealed that the presence of an ester moiety in the imidazole ring was required for full agonist properties, while modifications made in the phenyl rings affected potency and efficacy, with ethyl 2-(4-bromophenyl)-l-(2,4-dichlorophenyl)-1H4-imidazolecarboxylate showing the highest potency. These compounds potentiated the [H-3]GABA binding to rat brain membranes, suggesting a site of interaction different from that of GABA. As for etomidate, mutation of asparagine-265 in the beta 2 subunit of the GABA(A) receptor into serine reduced the ability of derivative 1i to modulate the GABA function.

  DOI：

  10.1021/jm049120y
• 作为产物：
  描述：

  2-苯基咪唑 在 palladium 10% on activated carbon 、 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 61.5h， 生成 4-(2-phenyl-1H-imidazol-1-yl)aniline
  参考文献：
  名称：

  含咪唑侧基的聚酰亚胺的设计，合成和气体渗透性能

  摘要：

  作为用于气体分离应用的新兴材料，含离子基团的成膜聚合物引起了广泛的关注。本文的目的是合成含有咪唑基团（PI-IMs）的新型成膜聚酰亚胺，并建立其结构与性能的关系。在这种情况下，一种新的芳族二胺，即N 1-（4-氨基苯基）-N 1-（4-（2-苯基-1H-咪唑-1-基）苯基）苯-1,4-二胺（ImTPADA ）合成并与三种芳族二酐，即4,4'-（六氟异亚丙基）二邻苯二甲酸酐，4,4-（4,4-异丙基二烯二苯氧基）双（邻苯二甲酸酐）和4,4'-氧基二邻苯二甲酸酐缩聚为形成相应的含有悬垂的2-苯基咪唑基团（PI-IEs）的聚酰亚胺。接下来，PI-IM由使用甲基碘将PI-6FDA中存在的2-苯基咪唑侧基进行N-季铵化，然后与双（三氟甲烷）磺酰亚胺锂盐（LiTf 2 N）进行阴离子交换。PI‐IE和PI‐IM表现出相当高的分子量，无定形性质，良好的溶解度，可以通过其DMAc溶液浇铸成自立式薄膜。热重

  DOI：

  10.1002/pola.29053

文献信息

• P2X4 RECEPTOR ANTAGONIST
  申请人：Nippon Chemiphar Co., Ltd.

  公开号：EP3020717B1

  公开（公告）日：2021-12-15
• US9840497B2
  申请人：——

  公开号：US9840497B2

  公开（公告）日：2017-12-12
• US9873683B2
  申请人：——

  公开号：US9873683B2

  公开（公告）日：2018-01-23
• Synthesis, Structure−Activity Relationships at the GABA_A Receptor in Rat Brain, and Differential Electrophysiological Profile at the Recombinant Human GABA_A Receptor of a Series of Substituted 1,2-Diphenylimidazoles
  作者：Battistina Asproni、Giuseppe Talani、Fabio Busonero、Amedeo Pau、Sebastiano Sanna、Riccardo Cerri、Maria Paola Mascia、Enrico Sanna、Giovanni Biggio

  DOI：10.1021/jm049120y

  日期：2005.4.1

  A series of new 1,2-diphenylimidazole derivatives (la-x) were synthesized and evaluated for their ability to potentiate gamma-aminobutyric acid (GABA)-evoked currents in Xenopus laevis oocytes expressing recombinant human GABAA receptors. Many of these compounds enhanced GABA action with potencies (EC50 = 0.19-19,mu M) and efficacies (maximal efficacies of up to 640%) similar to or greater than those of anesthetics such as etomidate, propofol, and alphaxalone. Structure- activity relationship analysis revealed that the presence of an ester moiety in the imidazole ring was required for full agonist properties, while modifications made in the phenyl rings affected potency and efficacy, with ethyl 2-(4-bromophenyl)-l-(2,4-dichlorophenyl)-1H4-imidazolecarboxylate showing the highest potency. These compounds potentiated the [H-3]GABA binding to rat brain membranes, suggesting a site of interaction different from that of GABA. As for etomidate, mutation of asparagine-265 in the beta 2 subunit of the GABA(A) receptor into serine reduced the ability of derivative 1i to modulate the GABA function.
• Design, synthesis, and gas permeation properties of polyimides containing pendent imidazolium groups
  作者：Bharat Shrimant、Ulhas K. Kharul、Prakash P. Wadgaonkar

  DOI：10.1002/pola.29053

  日期：2018.8.1

  anhydride, 4,4‐(4,4‐isopropylidenediphenoxy) bis(phthalic anhydride), and 4,4′‐oxydiphthalic anhydride to form the corresponding polyimides containing pendent 2‐phenylimidazole groups (PI‐IEs). Next, PI‐IMs were prepared by N‐quaternization of pendent 2‐phenylimidazole groups present in PI‐6FDA using methyl iodide followed by anion exchange with bis(trifluoromethane)sulfonimide lithium salt (LiTf2N).

  作为用于气体分离应用的新兴材料，含离子基团的成膜聚合物引起了广泛的关注。本文的目的是合成含有咪唑基团（PI-IMs）的新型成膜聚酰亚胺，并建立其结构与性能的关系。在这种情况下，一种新的芳族二胺，即N 1-（4-氨基苯基）-N 1-（4-（2-苯基-1H-咪唑-1-基）苯基）苯-1,4-二胺（ImTPADA ）合成并与三种芳族二酐，即4,4'-（六氟异亚丙基）二邻苯二甲酸酐，4,4-（4,4-异丙基二烯二苯氧基）双（邻苯二甲酸酐）和4,4'-氧基二邻苯二甲酸酐缩聚为形成相应的含有悬垂的2-苯基咪唑基团（PI-IEs）的聚酰亚胺。接下来，PI-IM由使用甲基碘将PI-6FDA中存在的2-苯基咪唑侧基进行N-季铵化，然后与双（三氟甲烷）磺酰亚胺锂盐（LiTf 2 N）进行阴离子交换。PI‐IE和PI‐IM表现出相当高的分子量，无定形性质，良好的溶解度，可以通过其DMAc溶液浇铸成自立式薄膜。热重