5-[(2E)-1-(1H-benzimidazol-2-yl)-3-(4-chlorophenyl)prop-2-en-1-ylidene]pyrimidine-2,4,6-(1H,3H,5H)-trione | 1417372-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-[(2E)-1-(1H-benzimidazol-2-yl)-3-(4-chlorophenyl)prop-2-en-1-ylidene]pyrimidine-2,4,6-(1H,3H,5H)-trione
• 英文别名: 5-[(E)-1-(1H-benzimidazol-2-yl)-3-(4-chlorophenyl)prop-2-enylidene]-1,3-diazinane-2,4,6-trione
• CAS: 1417372-98-5
• 化学式: C₂₀H₁₃ClN₄O₃
• 分子量: 392.801
• InChiKey: UQBILQKYXJRTNS-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103.95
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-(1-羟乙基)苯并咪唑 在 potassium dichromate 、 硫酸 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 19.33h， 生成 5-[(2E)-1-(1H-benzimidazol-2-yl)-3-(4-chlorophenyl)prop-2-en-1-ylidene]pyrimidine-2,4,6-(1H,3H,5H)-trione
  参考文献：
  名称：

  Microwave Assisted Synthesis, Physico-chemical Properties and Antioxidant Activity of a,b-Unsaturated Benzimidazole Derivatives Incorporated with Baritone Moiety

  摘要：

  通过传统方法和微波辅助方法合成了一系列 (2E)-1-(H- 苯并咪唑-2-基)-3-取代苯基 2-丙烯-1-酮与巴比妥（5a-g）的连接物。苯并咪唑查耳酮（4a-g）是由 2-乙酰基苯并咪唑（3a）与不同的芳香醛缩合而成。这些查耳酮在乙酸介质中与巴比妥酸反应后，得到了 a、b-不饱和苯并咪唑衍生物。根据红外光谱、1H NMR、质谱和元素分析，确定了所有最终化合物的结构。衍生物的药效和理化性质由 actelion、molsoft、molinspiration 和 ACD ChemDraw Ultra 11.0 软件测定。最终产品具有良好的药物相似性和药物评分。用 DPPH 法对所有最终合成的化合物进行了抗氧化性筛选，如清除自由基。在合成的化合物中，(5f)、(5c)和(5d)表现出良好的抗氧化活性，而所有其他衍生物则表现出中等活性。

  DOI：

  10.14233/ajchem.2013.13187

文献信息

• Antitumour activity of 5-[(2E)-1-(1H-benzimidazol-2-yl)-3-substituted phenylprop-2-en-1-ylidene] pyrimidine-2,4,6(1H,3H,5H)-triones against Dalton’s ascitic lymphoma in mice
  作者：Bijo Mathew、Jerad Suresh、Devaraji Vinod

  DOI：10.1007/s00044-012-0407-1

  日期：2013.8

  A new series of novel benzimidazole derivatives containing barbitone moiety (5a-f) was synthesized by a Knoevenagel condensation of (2E)-1-(1H-benzimidazol-2-yl)-3-phenylprop-2-en-1-ones (4a-f) and barbituric acid in the presence of catalytic amount of acetic acid medium. All the final structures were assigned on the basis of IR, H-1 NMR and mass spectra analysis. Acute toxicity studies were performed initially to determine the safety of titled derivatives and the ED (50) value was calculated 50 mg/kg. All the final derivatives were screened for antitumour activity against Dalton's ascitic lymphoma in mice. All the new candidates at a dose of 50 mg/kg showed a good antitumour activity against DLA-bearing mice when compared to the standard 5-fluro uracil. Among the final derivatives (5e), 5-[(2E)-1-(1H-benzimidazol-2-yl)-3-(3-nitrophenyl) prop-2-en-1-ylidene] pyrimidine-2,4,6(1H,3H,5H)-trione was found to be most potent antitumour in nature.
• Microwave Assisted Synthesis, Physico-chemical Properties and Antioxidant Activity of a,b-Unsaturated Benzimidazole Derivatives Incorporated with Baritone Moiety
  作者：Bijo Mathew、A. Jerad Suresh、S. Anbazhagan

  DOI：10.14233/ajchem.2013.13187

  日期：——

  A series of (2E)-1-(H-benzimidazol-2-yl)-3-substituted phenyl 2-propen-1-one linked with barbitone (5a-g) are synthesized by both conventional method and microwave assisted method. The benzimidazole chalcones (4a-g) were prepared from the condensation of 2-acetyl benzimidazole (3a) with different aromatic aldehydes. These chalcones on reaction with barbituric acid in presence of acetic acid medium gave the a,b-unsaturated benzimidazole derivatives. The structures of the all the final compounds were established on the basis of IR, 1H NMR, mass spectra and elemental analysis. The druglikeness and physicochemical properties of the derivatives were determined by actelion, molsoft, molinspiration and ACD ChemDraw Ultra 11.0 software. The final products possess a favourable drug likeness and drug score. All the final synthesized compounds were screened for their antioxidant properties like free radical scavenging by DPPH method. Among the synthesized compounds (5f), (5c) and (5d) were exhibited a good antioxidant activity and all the other derivatives showed a moderate activity.

  通过传统方法和微波辅助方法合成了一系列 (2E)-1-(H- 苯并咪唑-2-基)-3-取代苯基 2-丙烯-1-酮与巴比妥（5a-g）的连接物。苯并咪唑查耳酮（4a-g）是由 2-乙酰基苯并咪唑（3a）与不同的芳香醛缩合而成。这些查耳酮在乙酸介质中与巴比妥酸反应后，得到了 a、b-不饱和苯并咪唑衍生物。根据红外光谱、1H NMR、质谱和元素分析，确定了所有最终化合物的结构。衍生物的药效和理化性质由 actelion、molsoft、molinspiration 和 ACD ChemDraw Ultra 11.0 软件测定。最终产品具有良好的药物相似性和药物评分。用 DPPH 法对所有最终合成的化合物进行了抗氧化性筛选，如清除自由基。在合成的化合物中，(5f)、(5c)和(5d)表现出良好的抗氧化活性，而所有其他衍生物则表现出中等活性。