3-(4,5-diphenyl-1H-imidazol-2-yl)-2-methyl-1H-indole | 662150-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4,5-diphenyl-1H-imidazol-2-yl)-2-methyl-1H-indole
• 英文别名: 1H-Indole, 3-(4,5-diphenyl-1H-imidazol-2-yl)-2-methyl-
• CAS: 662150-78-9
• 化学式: C₂₄H₁₉N₃
• 分子量: 349.435
• InChiKey: HLKACVLWVUPWAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基吲哚-3-甲醛 、 联苯甲酰 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 3-(4,5-diphenyl-1H-imidazol-2-yl)-2-methyl-1H-indole
  参考文献：
  名称：

  三取代咪唑通过靶向致癌PI3K / Akt / mTOR信号通路来诱导人乳腺癌细胞凋亡。

  摘要：

  PI3K / Akt / mTOR的过度活化与致癌作用相关，在治疗各种癌症中起潜在的分子治疗靶标的作用。在这里，我们报告了三取代咪唑的合成，并确定了2-氯-3-（4,5-二苯基-1H-咪唑-2-基）吡啶（CIP）作为主要的细胞毒剂。计算机靶标预测的朴素基础分类器模型显示，CIP靶向包括Akt的RAC-β丝氨酸/苏氨酸-蛋白激酶。此外，CIP下调了Akt，PDK和mTOR蛋白的磷酸化，降低了细胞周期蛋白D1，Bcl-2，存活蛋白，VEGF，procaspase-3的表达，并增强了PARP的裂解。此外，CIP显着下调了CXCL12诱导的乳腺癌细胞运动性，分子对接计算显示，与先前报道的Akt2抑制剂库相比，所有化合物均以较高的对接分数与Akt2激酶结合。总之，我们报告了通过负调节PI3K / Akt / mTOR信号通路诱导乳腺癌细胞凋亡的咪唑的合成和生物学评估。

  DOI：

  10.1371/journal.pone.0153155

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。
• Potent antimicrobial activity of 3-(4,5-diaryl-1H-imidazol-2-yl)-1H-indole derivatives against methicillin-resistant Staphylococcus aureus
  作者：Raed A. Al-Qawasmeh、Mario Huesca、Venkata Nedunuri、Robert Peralta、Jim Wright、Yoon Lee、Aiping Young

  DOI：10.1016/j.bmcl.2010.04.137

  日期：2010.6

  A new series of antimicrobial derivatives [3-(4,5-diaryl-1H-imidazol-2-yl)-1H-indole)] have been synthesized with potent activity against strains of Staphylococcus aureus, including methicillin-resistant strains (MRSA). Compound 17 [3-(4,5-bis(4-fluorophenyl)-1H-imidazol-2-yl)-5-bromo-1H-indole], the most active derivative was shown to inhibit the growth of all Gram-positive strains tested, including vancomycin resistant Enterococcus faecalis and Enterococcus faecium with no activity against Gram-negative bacteria. (C) 2010 Elsevier Ltd. All rights reserved.
• [EN] 2,4,5-TRISUBSTITUTED IMIDAZOLES AND THEIR USE AS ANTI-MICROBIAL AGENTS<br/>[FR] IMIDAZOLES 2,4,5-TRISUBSTITUES ET UTILISATION DE CEUX-CI COMME AGENTS ANTI-MICROBIENS
  申请人：LORUS THERAPEUTICS INC

  公开号：WO2004016086A3

  公开（公告）日：2004-04-29
• 2,4,5-TRISUBSTITUTED IMIDAZOLES AND THEIR USE AS ANTI-MICROBIAL AGENTS
  申请人：Lorus Therapeutics Inc.

  公开号：EP1531674B1

  公开（公告）日：2014-06-18
• 2, 4, 5 - Trisubstituted Imidazoles And Their Use As Anti-Microbial Agents
  申请人：Al-Qawasmeh Raed

  公开号：US20070105929A1

  公开（公告）日：2007-05-10

  The present invention provides therapeutically effective 2,4,5-trisubstituted imidazole compounds, methods of preparing the same, and compositions comprising the compounds alone or in combination with other agents. The present invention further provides for the use of the compounds as anti-microbial agents. The anti-microbial properties of the compounds include anti-bacterial and/or anti-fungal activity.