3-(4-(1H-imidazol-1-yl)phenyl)-1-phenylprop-2-en-1-one | 1392592-94-7

• 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-phenylprop-2-en-1-one
• 英文别名: 3-(4-(1h-Imidazol-1-yl) phenyl)-1phenylprop-2-en-1-one；3-(4-imidazol-1-ylphenyl)-1-phenylprop-2-en-1-one
• CAS: 1392592-94-7
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: CZQSCAXMOZRWIK-UHFFFAOYSA-N

物化性质

• 沸点：
  478.9±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙酰基吡啶 、 3-(4-(1H-imidazol-1-yl)phenyl)-1-phenylprop-2-en-1-one 在 sodium hydroxide 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 10.5h， 以45%的产率得到6-(4-imidazol-1-ylphenyl)-2,4-dihydroxy-2-(pyridine-2-yl)-4-phenyl-1-(pyridine-2-ylcarbonyl)cyclohexane
  参考文献：
  名称：

  Synthesis and Crystal Structure of New Pyridyl Derivative

  摘要：

  采用基于无溶剂反应的高效合成方法制备了具有四个立体中心的吡啶基衍生物。通过元素分析、IR、1H NMR、质谱和单晶X射线衍射对其结构进行了表征。晶体结构表明环己基为椅式构象，三个分子内氢键生成三聚体。

  DOI：

  10.14233/ajchem.2014.17269
• 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-phenylprop-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

• Synthesis and Crystal Structure of New Pyridyl Derivative
  作者：Xinping Ge、Wei Li、Fuying Hao、Shengli Li、Feng Jin、Hongping Zhou

  DOI：10.14233/ajchem.2014.17269

  日期：——

  A pyridyl derivative with four stereo centers has been prepared by an efficient synthetic method based on a solvent-free reaction. The structure was characterized by elemental analyses, IR, 1H NMR, mass spectra and single crystal X-ray diffraction. The crystal structure shows that the cyclohexyl group is a chair conformation and three intramolecular hydrogen bonds generate the trimer.

  采用基于无溶剂反应的高效合成方法制备了具有四个立体中心的吡啶基衍生物。通过元素分析、IR、1H NMR、质谱和单晶X射线衍射对其结构进行了表征。晶体结构表明环己基为椅式构象，三个分子内氢键生成三聚体。
• 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.
• 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 evaluation of 2,4,6-trisubstituted pyrimidine derivatives as novel antileishmanial agents
  作者：S. K. Patle、N. Kawathekar、M. Zaveri、P. Kamaria

  DOI：10.1007/s00044-012-0167-y

  日期：2013.4

  A series of new 2,4,6-trisubstituted pyrimidine derivatives 8(a-j) were synthesized by reacting substituted chalcones containing imidazole 6(a-d) and benzimidazole 7(a-f) with guanidine hydrochloride in the presence of strong base. Substituted chalcones were synthesized by reacting 4-(1H-imidazol-1-yl)benzaldehyde or 4-(1H-benzo[d]imidazol-1-yl)benzaldehyde with different substituted acetophenones in the presence of 40 % NaOH in methanol. The synthesized compounds were confirmed by IR, (HNMR)-H-1, and mass spectral data and screened for antileishmanial activity. Antileishmanial activity was performed against Leishmania donovani parasite, and percentage lysis inhibition were calculated by meglumine antimoliate taking a positive control and chloroform (0.1 % CHCl3) treatment served as control. Among all the compounds, 8h and 8j exhibited 50-57 % inhibition against promastigotes, thus providing new structural lead for antileishmanials.