3-(4-(1H-imidazol-1-yl)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one | 1392592-97-0

• 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-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 3-(4-imidazol-1-ylphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 1392592-97-0
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: NMZQJFTYLPPRPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  盐酸胍 、 3-(4-(1H-imidazol-1-yl)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one 在 potassium hydroxide 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以55%的产率得到4-(4-(1H-imidazol-1-yl)phenyl)-6-(4-methoxyphenyl)pyrimidin-2-amine
  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
• 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-(4-methoxyphenyl)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

• 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.