1-甲基-2-(4-硝基苯基)-4,5-二苯基-1H-咪唑 | 36783-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-甲基-2-(4-硝基苯基)-4,5-二苯基-1H-咪唑
• 英文名称: 1-methyl-2-(4-nitrophenyl)-4,5-diphenylimidazole
• 英文别名: 1-methyl-2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazole；1-Methyl-4,5-diphenyl-2-<4-nitrophenyl>-imidazol
• CAS: 36783-81-0
• 化学式: C₂₂H₁₇N₃O₂
• 分子量: 355.396
• InChiKey: KPTDAVDOBQBDQH-UHFFFAOYSA-N

物化性质

• 熔点：
  198 °C
• 沸点：
  554.0±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-甲基-2-(4-硝基苯基)-4,5-二苯基-1H-咪唑 在 palladium on activated charcoal potassium carbonate 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 25.0h， 生成 N,N',N''-tris-[4-(1-methyl-4,5-diphenyl-1H-imidazol-2-yl)-phenyl]-[1,3,5]triazine-2,4,6-triamine
  参考文献：
  名称：

  Synthesis and antibacterial activity of various substituted s-triazines

  摘要：

  Series of substituted-s-triazines (1-22) were synthesized and evaluated for their in vitro antibacterial activity against six representative Gram-positive and Gram-negative bacterial strains. Many compounds have displayed comparable antibacterial activity against Bacillus sphaericus and significantly active against other tested organisms with reference to streptomycin. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.05.013
• 作为产物：
  描述：

  联苯甲酰 在 乙酸铵 、 potassium carbonate 作用下， 以 溶剂黄146 为溶剂， 生成 1-甲基-2-(4-硝基苯基)-4,5-二苯基-1H-咪唑
  参考文献：
  名称：

  New class of imidazoles incorporated with thiophenevinyl conjugation pathway for robust nonlinear optical chromophores

  摘要：

  A new series of thermally stable heterocyclic imidazole-based nonlinear optical chromophores has been developed. These chromophores possess a thiophene based stilbene conjugation pathway with a nitro acceptor group attached to the phenyl end. This feature leads to robust chromophores with high thermal stability and enhanced molecular nonlinearity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02143-2

文献信息

• Synthesis and biological evaluation of 1,2,4,5-tetrasubstituted imidazoles
  作者：Yue Fang、Rui Yuan、Wen-hui Ge、Yuan-jiang Wang、Gui-xiang Liu、Ming-qi Li、Jiang-biao Xu、Yu Wan、Sheng-liang Zhou、Xi-guang Han、Peng Zhang、Jin-juan Liu、Hui Wu

  DOI：10.1007/s11164-017-2886-7

  日期：2017.8

  Tetrasubstituted imidazoles were synthesized in high yields via the four-component reaction of aromatic aldehydes, amines, substituted benzils and ammonium acetate catalyzed by a porous CeO2 nanorod. Their anti-cancer activities on the Huh-7 hepatocellular carcinoma cell and antibacterial activities on four bacterial species (wild-type Escherichia coli, wild-type Staphylococcus aureus, Pseudomonas

  通过多孔CeO 2纳米棒催化的芳族醛，胺，取代的苯甲酰胺和乙酸铵的四组分反应，高产率合成了四取代的咪唑。评估了它们对Huh-7肝癌细胞的抗癌活性以及对四种细菌种类（野生型大肠杆菌，野生型金黄色葡萄球菌，铜绿假单胞菌PAM1032和大肠杆菌-NMD-1）的抗菌活性。筛选出一种化合物（5p）是因为它对所有四种细菌的100μg/ mL的高抑制率。三种产品（5p，5t和5y）在10μg/ mL的浓度下对Huh-7肝癌细胞具有较高的抑制率。结果表明了它们在新药开发中的潜力。
• Synthesis of 2-substituted-N-[4-(1-methyl-4,5-diphenyl-1H-imidazole-2-yl)phenyl]acetamide derivatives and evaluation of their anticancer activity
  作者：Yusuf Özkay、İlhan Işıkdağ、Zerrin İncesu、Gülşen Akalın

  DOI：10.1016/j.ejmech.2010.04.015

  日期：2010.8

  In the present study 18 novel imidazole-(benz)azole and imidazole-piperazine derivatives were synthesized in order to investigate their probable anticancer activity. The structures of the compounds were confirmed by IR, H-1 NMR and EI-MS spectral data. Cytotoxicity (MTT), analysis of DNA synthesis and detection of apoptotic DNA assays were applied to determine anticancer activity of the compounds against colon (HT-29) and breast (MCF-7) carcinoma cell lines. Most of the compounds, showed greater activity against HT-29 cells than MCF-7 cells. Some of them indicated considerable cytotoxicity against both of the carcinogenic cell lines. However, their inhibitory activity on DNA synthesis was relatively poor. Anticancer activity screening results revealed that 11, 12 and 13 were the most active compounds in the series. They exhibited significant cytotoxicity against both of the carcinogenic cell lines and caused DNA fragmentation of the HT-29 cells. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Triarylimidazole Redox Catalysts: Electrochemical Analysis and Empirical Correlations
  作者：Ni-tao Zhang、Cheng-chu Zeng、Chiu Marco Lam、Randi K. Gbur、R. Daniel Little

  DOI：10.1021/jo302309m

  日期：2013.3.1

  A series of triarylimidazoles was synthesized and characterized electrochemically. The synthetic route is general, providing a pathway to 30 redox mediators that exhibit a > 700 mV range of accessible potentials. Most of the triarylimidazoles display three oxidation peaks where the first redox couple is quasi-reversible. The electronic character of the substituents affects the oxidation potential. This is exemplified by a linear correlation between the first oxidation potential and the sum of the Hammett sigma(+) substituent constants, as well as with a series of calculated ionization potentials. We close by putting forward a rule of thumb stating that for a given mediator, the upper limit of accessible potentials can be extended by at least 500 mV beyond the largest recorded value. A rationale, the conditions under which the rule is likely to apply, and an example are provided.
• CAHAEBA EH. P.; TANASEJCHUK B. S., MORDOVSK. YH-T., CAPAHCK, 1981. 6 S., BIBLIOGR. 2 NAZV. (PYK DEP V ONIITE+
  作者：CAHAEBA EH. P.、 TANASEJCHUK B. S.

  DOI：——

  日期：——
• New class of imidazoles incorporated with thiophenevinyl conjugation pathway for robust nonlinear optical chromophores
  作者：Javier Santos、Eric A Mintz、Oliver Zehnder、Christian Bosshard、Xiu R Bu、Peter Günter

  DOI：10.1016/s0040-4039(00)02143-2

  日期：2001.1

  A new series of thermally stable heterocyclic imidazole-based nonlinear optical chromophores has been developed. These chromophores possess a thiophene based stilbene conjugation pathway with a nitro acceptor group attached to the phenyl end. This feature leads to robust chromophores with high thermal stability and enhanced molecular nonlinearity. (C) 2001 Elsevier Science Ltd. All rights reserved.