3-(4-(1H-imidazol-1-yl)phenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4-(1H-imidazol-1-yl)phenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(3,4-dimethoxyphenyl)-3-[4-(1H-imidazol-1-yl)phenyl]prop-2-en-1-one；3-(4-(1h-Imidazol-1-yl) phenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one；1-(3,4-dimethoxyphenyl)-3-(4-imidazol-1-ylphenyl)prop-2-en-1-one
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: QOAXMLYUICTIPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-(1H-imidazol-1-yl)phenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one 、 溶剂黄146 在 一水合肼 作用下， 反应 4.0h， 生成 1-(5-(4-(1H-imidazol-1-yl)phenyl)-3-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  新型 2-吡唑啉衍生物作为治疗阿尔茨海默病的多功能药物的合成、分子对接和生物学评价。

  摘要：

  设计、合成了一系列新的 2-吡唑啉衍生物，并评估了胆碱酯酶 (ChE) 抑制、Aβ 抗聚集和神经保护活性。其中，3d、3e、3g 和 3h 被确定为最有效和选择性最强的 BChE 抑制剂（IC50 = 0.5-3.9 μM），而 3f 对 BChE 和 AChE 具有双重抑制活性（IC50 = 6.0 和 6.5 μM，分别） . 动力学分析表明，3g 是 BChE 的部分非竞争性抑制剂（Ki = 2.22 μM），而 3f 对 AChE 具有竞争性抑制作用（Ki = 0.63 μM）。随后筛选活性化合物以进行进一步评估。3f、3g 和 3h 显着降低了 Aβ1-42 的聚集水平（分别为 72.6、83.4 和 63.4%）。此外，3f 对 Aβ1-42 诱导和 H2O2 诱导的细胞毒性表现出出色的神经保护作用 (95. 分别为 6% 和 93.6%）。用 3g 和 3f 进行分子对接研究以研究

  DOI：

  10.1039/c9md00030e
• 作为产物：
  描述：

  对氟苯甲醛 在 十六烷基三甲基溴化铵 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 3-(4-(1H-imidazol-1-yl)phenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and biological studies of a novel series of 4-(4-(1H-imidazol-1-yl)phenyl)-6-arylpyrimidin-2-amines

  摘要：

  A novel series of eleven 4-(4-(1H-imidazol-1-yl)phenyl)-6-arylpyrimidin-2-amines has been prepared from synthesized 3-[4-(1H-imidazol-1-yl) phenyl]prop-2-en-1-ones and evaluated for phosphodiesterase (PDE) inhibition and antimicrobial activities. N-arylation of imidazole with 4-fluorobenzaldehyde using hexadecyltrimethylammonium bromide as catalyst gave 4-(1H-imidazol-1-yl) benzaldehyde which on treatment with substituted acetophenones yielded corresponding chalcones (1a-1k). Each chalcone on further reaction with guanidine hydrochloride resulted in title compounds (2a-2k). Pyrimidines thus synthesized were subjected to biological studies. Some compounds showed marked activities in PDE inhibition and anti-bacterial and anti-fungal bioassays.

  DOI：

  10.1007/s00044-013-0523-6

文献信息

• Anti-oxidant, anti-fungal and anti-leishmanial activities of novel 3-[4-(1H-imidazol-1-yl) phenyl]prop-2-en-1-ones
  作者：Tanvir Hussain、Hamid Latif Siddiqui、Muhammad Zia-ur-Rehman、Muhammad Masoom Yasinzai、Masood Parvez

  DOI：10.1016/j.ejmech.2009.06.038

  日期：2009.11

  A series of new 3-[4-(1H-imidazol-1-yl) phenyl]prop-2-en-1-ones were synthesized by the condensation of various acetophenones with 4-(1H-imidazol-1-yl) benzaldehyde which was itself prepared by the N-arylation of imidazole using hexadecyltrimethylammonium bromide as catalyst for the first time. All the synthesized compounds were subjected to preliminary evaluation for their anti-leishmanial, anti-oxidant and anti-fungal activities. Few of the synthesized compounds showed significant activities. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological studies of a novel series of 4-(4-(1H-imidazol-1-yl)phenyl)-6-arylpyrimidin-2-amines
  作者：Mujahid Hussain Bukhari、Matloob Ahmad、Tanvir Hussain、Syed Umar、Naveed Ahmad

  DOI：10.1007/s00044-013-0523-6

  日期：2013.11

  A novel series of eleven 4-(4-(1H-imidazol-1-yl)phenyl)-6-arylpyrimidin-2-amines has been prepared from synthesized 3-[4-(1H-imidazol-1-yl) phenyl]prop-2-en-1-ones and evaluated for phosphodiesterase (PDE) inhibition and antimicrobial activities. N-arylation of imidazole with 4-fluorobenzaldehyde using hexadecyltrimethylammonium bromide as catalyst gave 4-(1H-imidazol-1-yl) benzaldehyde which on treatment with substituted acetophenones yielded corresponding chalcones (1a-1k). Each chalcone on further reaction with guanidine hydrochloride resulted in title compounds (2a-2k). Pyrimidines thus synthesized were subjected to biological studies. Some compounds showed marked activities in PDE inhibition and anti-bacterial and anti-fungal bioassays.
• Synthesis, molecular docking, and biological evaluation of novel 2-pyrazoline derivatives as multifunctional agents for the treatment of Alzheimer's disease
  作者：Oya Unsal-Tan、Tuba Tüylü Küçükkılınç、Beyza Ayazgök、Ayla Balkan、Keriman Ozadali-Sari

  DOI：10.1039/c9md00030e

  日期：——

  A novel series of 2-pyrazoline derivatives were designed, synthesized, and evaluated for cholinesterase (ChE) inhibitory, Aβ anti-aggregating and neuroprotective activities. Among these, 3d, 3e, 3g, and 3h were established as the most potent and selective BChE inhibitors (IC50 = 0.5-3.9 μM), while 3f presented dual inhibitory activity against BChE and AChE (IC50 = 6.0 and 6.5 μM, respectively). Kinetic

  设计、合成了一系列新的 2-吡唑啉衍生物，并评估了胆碱酯酶 (ChE) 抑制、Aβ 抗聚集和神经保护活性。其中，3d、3e、3g 和 3h 被确定为最有效和选择性最强的 BChE 抑制剂（IC50 = 0.5-3.9 μM），而 3f 对 BChE 和 AChE 具有双重抑制活性（IC50 = 6.0 和 6.5 μM，分别） . 动力学分析表明，3g 是 BChE 的部分非竞争性抑制剂（Ki = 2.22 μM），而 3f 对 AChE 具有竞争性抑制作用（Ki = 0.63 μM）。随后筛选活性化合物以进行进一步评估。3f、3g 和 3h 显着降低了 Aβ1-42 的聚集水平（分别为 72.6、83.4 和 63.4%）。此外，3f 对 Aβ1-42 诱导和 H2O2 诱导的细胞毒性表现出出色的神经保护作用 (95. 分别为 6% 和 93.6%）。用 3g 和 3f 进行分子对接研究以研究