2-(p-dimethylaminophenyl)phenanthro[9,10-d]imidazole | 36939-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(p-dimethylaminophenyl)phenanthro[9,10-d]imidazole
• 英文别名: N,N-dimethyl-4-(1H-phenanthro[9,10-d]imidazol-2-yl)aniline；4-(1H-phenanthro[9,10-d]imidazol-2-yl)-N,N-dimethylbenzenamine；2-(p-Dimethylaminophenyl)phenanthro<9,10-d>imidazol；2-(4-N,N-dimethylanilino)-1H-phenanthro[9,10-d]imidazole；N,N-Dimethyl-4-(1H-phenanthro[9,10-d]imidazol-2-yl)-anilin
• CAS: 36939-51-2
• 化学式: C₂₃H₁₉N₃
• 分子量: 337.424
• InChiKey: BUEZUAOVMMOSGA-UHFFFAOYSA-N

物化性质

• 熔点：
  261-262 °C
• 沸点：
  611.7±57.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(p-dimethylaminophenyl)phenanthro[9,10-d]imidazole 在 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 3-(2-(4-(dimethylamino)phenyl)-1H-phenanthro[9,10-d]-imidazole-1-yl)-N-(2-(ethylamino)-2-oxoethyl)-N,N-dimethylpropan-1-aminium bromide
  参考文献：
  名称：

  Development of Membrane-Targeting Fluorescent 2-Phenyl-1H-phenanthro[9,10-d]imidazole-Antimicrobial Peptide Mimic Conjugates against Methicillin-Resistant Staphylococcus aureus

  摘要：

  DOI：

  10.1021/acs.jmedchem.4c00436
• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 菲醌 在 ammonium acetate 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 0.1h， 以92%的产率得到2-(p-dimethylaminophenyl)phenanthro[9,10-d]imidazole
  参考文献：
  名称：

  多组分一锅法合成2-芳基-1H-菲[9,10-d]咪唑的新方法

  摘要：

  摘要报道了一种新型的酸催化多组分一锅法合成由芳香醛、9,10-菲醌和醋酸铵衍生的 2-芳基-1H-菲[9,10-d]咪唑化合物在超声辐照下。在优化的条件下，多种芳香醛很容易与 9,10-菲醌和乙酸铵缩合，从而以优异的收率提供所需的高纯度咪唑。

  DOI：

  10.1515/hc.2011.018

文献信息

• [EN] ARYL IMIDAZOLES AND THEIR USE AS ANTI-CANCER AGENTS<br/>[FR] IMIDAZOLES D'ARYLE ET LEUR UTILISATION COMME AGENTS ANTICANCEREUX
  申请人：LORUS THERAPEUTICS INC

  公开号：WO2005047266A1

  公开（公告）日：2005-05-26

  Therapeutically effective 2,4,5-trisubstituted imidazole compounds are provided. Also provided are methods -of preparing the compounds and pharmaceutical compositions comprising the compounds alone or in combination with other agents. The present invention further provides for the use of the compounds as anti-cancer agents; wherein: R1 is aryl, substituted aryl, heterocycle, substituted heterocycle, heteroaryl, substituted hetéroaryl or amino; R2 and R3 are independently aryl, substituted aryl, heterocycle, heteroaryl, substituted heterocycle, or substituted heteroaryl or R2 and R3 when taken together along with the carbon atoms they are attached to, form aryl or substituted aryl, and R4 is hydrogen, halogen, hydroxyl, thiol, lower alkyl, substituted lower alkyl, lower alkenyl, substituted lower alkenyl, lower alkynyl, substituted lower alkynyl, alkylalkenyl, alkyl alkynyl, alkoxy, alkyithio, aryl, aryloxy, amino, amido, carboxyl, aryl, substituted aryl, heterocycle, heteroaryl, substituted heterocycle, heteroalkyl, cycloalkyl, substituted cycloalkyl, alkylcycloalkyl, alkylcyclobeteroalkyl, nitro, cyano or -S(O)o.2R wherein R is alkyl, substituted alkyl, aryl, substituted aryl, heterocycle, beteroaryl, substituted heterocycle, or substituted heteroaryl.

  提供了具有治疗效果的2,4,5-三取代咪唑化合物。还提供了制备这些化合物的方法以及包含这些化合物单独或与其他药剂组合的药物组合物。本发明进一步提供了将这些化合物用作抗癌剂的用途；其中：R1为芳基，取代芳基，杂环，取代杂环，杂芳基，取代杂芳基或氨基；R2和R3独立地为芳基，取代芳基，杂环，杂芳基，取代杂环，或取代杂芳基，或者R2和R3当结合在一起时与它们连接的碳原子形成芳基或取代芳基，而R4为氢，卤素，羟基，硫醇，低烷基，取代低烷基，低烯基，取代低烯基，低炔基，取代低炔基，烷基烯基，烷基炔基，烷氧基，烷硫基，芳基，芳氧基，氨基，酰胺基，羧基，芳基，取代芳基，杂环，杂芳基，取代杂环，杂烷基，环烷基，取代环烷基，烷基环烷基，烷基环杂烷基，硝基，氰基或-S(O)o.2R，其中R为烷基，取代烷基，芳基，取代芳基，杂环，杂芳基，取代杂环，或取代杂芳基。
• New approach to the multicomponent one-pot synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazoles
  作者：Saman Damavandi

  DOI：10.1515/hc.2011.018

  日期：2011.1.1

  Abstract A novel, acid catalyzed multicomponent one-pot synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazole compounds derived from aromatic aldehydes, 9,10-phenanthrenequinone and ammonium acetate under ultrasonic irradiation is reported. A wide range of aromatic aldehydes readily undergo condensation with 9,10-phenanthrenequinone and ammonium acetate under optimized conditions to afford the desired

  摘要报道了一种新型的酸催化多组分一锅法合成由芳香醛、9,10-菲醌和醋酸铵衍生的 2-芳基-1H-菲[9,10-d]咪唑化合物在超声辐照下。在优化的条件下，多种芳香醛很容易与 9,10-菲醌和乙酸铵缩合，从而以优异的收率提供所需的高纯度咪唑。
• Urea–Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel
  作者：Cristian Ochoa-Puentes、Natalia Higuera、Diana Peña-Solórzano

  DOI：10.1055/s-0037-1610679

  日期：2019.1

  The low-melting mixture urea–ZnCl2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1H-imidazoles or 2-aryl-1H-phenanthro[9,10-d]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.

  低熔点混合物尿素-ZnCl2 被评估为一种新颖的反应介质，用于合成咪唑类化合物。二羰基化合物、醋酸铵和芳香醛之间的反应在共熔溶剂的高效催化下进行，产生了各种三芳基-1H-咪唑或2-芳基-1H-苯并[9,10-d]咪唑，收率良好至优异。此外，该共熔溶剂在五个循环中被重复使用，且没有失去其催化活性。该方案进一步用于合成药物三芬格雷，产率优异。
• A novel imidazolium-based acidic ionic liquid as an efficient and reusable catalyst for the synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazoles
  作者：Hossein Eshghi、Mohammad Rahimizadeh、Maede Hasanpour、Mehdi Bakavoli

  DOI：10.1007/s11164-013-1522-4

  日期：2015.7

  A novel acidic ionic liquid based on imidazoliumcation is designed, synthesized, and successfully used as a catalyst for the one-pot synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazole derivatives. The remarkable feature of this new catalyst is its ethyleneoxy bridge which participates in dissolving organic compounds in ionic liquids. The application of this acidic ionic liquid is studied in a new one-pot

  设计，合成了一种新型的基于咪唑鎓阳离子的酸性离子液体，并成功地用作一锅合成2-芳基-1 H-菲[9,10 - d ]咪唑衍生物的催化剂。这种新催化剂的显着特点是它的亚乙基氧基桥参与了将有机化合物溶解在离子液体中。在一种新的一锅法中研究这种酸性离子液体在无溶剂条件下合成咪唑衍生物的应用。该方法的优点是催化剂的可重复使用性，高转化率，较短的反应时间和简单的实验程序。
• Carbamodithioate-based fluorescent chemosensor for Hg(II): a staged response approach and investigation into the sensing mechanism
  作者：Xiaohong Cheng、Zhicheng Zhong、Tingting Ye、Bingjie Zhang

  DOI：10.1002/bio.3205

  日期：2017.6

  Carbamodithioate-based compound C1 was designed and synthesized as a new fluorescent probe for Hg2+ ions. Upon the addition of Hg2+ ions, it displayed a rare staged response: the emission spectra of C1 first showed an apparent red-shift, followed by a dramatic decrease. To investigate the sensing mechanism, control compounds C2 with the same phenanthroimidazole unit and C3 with the same carbamodithioate functionality were synthesized. On comparison, the first step sensing process was ascribed to decreasing photoinduced electron transfer on the coordination of Hg2+ with the lone pair electrons of the nitrogen atom on the phenanthroimidazole ring. The affinity of Hg2+ and the carbamodithioate unit with four sulfur atoms then induced changes in intramolecular charge transfer efficiency and the second step fluorescent response.

  我们设计并合成了以二硫代氨基甲酸盐为基础的化合物 C1，作为一种新的 Hg2+ 离子荧光探针。当加入 Hg2+ 离子时，它显示出罕见的阶段性反应：C1 的发射光谱首先出现明显的红移，随后急剧下降。为了研究其传感机制，我们合成了具有相同菲咯咪唑单元的对照化合物 C2 和具有相同二硫代氨基甲酸盐官能团的 C3。经比较，第一步传感过程归因于 Hg2+ 与菲啰咪唑环上氮原子的孤对电子配位时光诱导电子转移的减少。然后，Hg2+ 与带有四个硫原子的二硫代氨基甲酸酯单元的亲和力诱导了分子内电荷转移效率和第二步荧光响应的变化。