(E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-phenylprop-2-en-1-one | 1332222-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-phenylprop-2-en-1-one
• 英文别名: (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-phenylprop-2-enone；(E)-3-(2-butyl-5-chloro-3-methylimidazol-4-yl)-1-phenylprop-2-en-1-one
• CAS: 1332222-82-8
• 化学式: C₁₇H₁₉ClN₂O
• 分子量: 302.804
• InChiKey: FWFVSHNEDYHCJD-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-phenylprop-2-en-1-one 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以74%的产率得到5-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-3-phenyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  新型强效抗菌剂吡唑苯并咪唑衍生物的设计、合成和分子对接研究

  摘要：

  合成了一系列新型吡唑苯并咪唑衍生物，并通过红外、质谱、13C NMR和1H NMR谱分析确认了最终目标4a-h的结构。具有咪唑和苯并咪唑衍生物的新型吡唑核心对六种细菌菌株的体外抗菌、抗真菌活性进行了显着评价。在分散体中，4c、4f和4g对枯草芽孢杆菌B29、大肠杆菌E266这三种微生物的抗菌活性最高，抑菌圈分别为21、19和19 mm。化合物4a、4c、4h对A.niger、Fusarium oxysporum真菌菌株表现出良好的抗真菌活性。此外，使用来自金黄色葡萄球菌的 C(30) 类胡萝卜素脱氢角鲨烯合酶与双膦酸盐 BPH-700 复合的晶体结构进行了蛋白质配体相互作用的分子对接。最终化合物中，4e、4g 和 4h 分别显示出最高的结合能 ΔG = -7.89、-7.48 和 -7.08 Kcal/mol，以及氨基酸相互作用 Lys273、Asp27。

  DOI：

  10.14233/ajchem.2019.22137
• 作为产物：
  描述：

  咪唑醛 在 sodium hydride 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  Synthesis and evaluation of novel 2-butyl-4-chloro-1-methylimidazole embedded chalcones and pyrazoles as angiotensin converting enzyme (ACE) inhibitors

  摘要：

  A series of novel 2-butyl-4-chloro-1-methylimidazole embedded aryl and heteroaryl derived chalcones and pyrazoles were synthesized and evaluated for their angiotensin converting enzyme (ACE) inhibitory activity. The condensation of 2-butyl-4-chloro-1-methylimidazole-5-carboxaldehyde with various aryl and heteroaryl methyl ketones in the presence of 10% aqueous NaOH in methanol proceeded efficiently to give the respective chalcones in very good yields. Further, the reaction of chalcones with hydrazine hydrate in acetic acid gave substituted pyrazole analogues. Screening all 36 new compounds using ACE inhibition assay, resulted chalcones with better ACE inhibitory activity compared to the respective pyrazole analogues. Among the chalcones 4a-r, three compounds, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(5-chlorothiophen-2-yl)prop-2-enone 4i, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(1H-pyrrol-2-yl)prop-2-enone 4l, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(dibenzo[b,d] thiophen-2-yl)prop-2-enone 4q were resulted as most active ACE inhibitors with IC50 of 3.60 mu M, 2.24 mu M, and 2.68 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.085

文献信息

• Synthesis and evaluation of novel 2-butyl-4-chloro-1-methylimidazole embedded chalcones and pyrazoles as angiotensin converting enzyme (ACE) inhibitors
  作者：Srinivas Kantevari、Dinesh Addla、Pankaj K. Bagul、Balasubramanian Sridhar、Sanjay K. Banerjee

  DOI：10.1016/j.bmc.2011.06.085

  日期：2011.8

  A series of novel 2-butyl-4-chloro-1-methylimidazole embedded aryl and heteroaryl derived chalcones and pyrazoles were synthesized and evaluated for their angiotensin converting enzyme (ACE) inhibitory activity. The condensation of 2-butyl-4-chloro-1-methylimidazole-5-carboxaldehyde with various aryl and heteroaryl methyl ketones in the presence of 10% aqueous NaOH in methanol proceeded efficiently to give the respective chalcones in very good yields. Further, the reaction of chalcones with hydrazine hydrate in acetic acid gave substituted pyrazole analogues. Screening all 36 new compounds using ACE inhibition assay, resulted chalcones with better ACE inhibitory activity compared to the respective pyrazole analogues. Among the chalcones 4a-r, three compounds, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(5-chlorothiophen-2-yl)prop-2-enone 4i, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(1H-pyrrol-2-yl)prop-2-enone 4l, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(dibenzo[b,d] thiophen-2-yl)prop-2-enone 4q were resulted as most active ACE inhibitors with IC50 of 3.60 mu M, 2.24 mu M, and 2.68 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Design, Synthesis and Molecular Docking Studies of Novel Pyrazole Benzimidazole Derivatives as Potent Antibacterial Agents
  作者：Srinivasa Rao Dasari、Subbaiah Tondepu、Lakshmana Rao Vadali、Nareshvarma Seelam

  DOI：10.14233/ajchem.2019.22137

  日期：2019.11.30

  A novel series of pyrazole benzimidazole derivatives were synthesized and the structure of the final targets 4a-h were confirmed by IR, Mass, 13C NMR and 1H NMR spectral analysis. The new pyrazole core with imidazole and benzimidazoles derivatives were evaluated for in vitro antibacterial, antifungal activity against six bacterial strains significantly. In dispersion, 4c, 4f and 4g had the highest

  合成了一系列新型吡唑苯并咪唑衍生物，并通过红外、质谱、13C NMR和1H NMR谱分析确认了最终目标4a-h的结构。具有咪唑和苯并咪唑衍生物的新型吡唑核心对六种细菌菌株的体外抗菌、抗真菌活性进行了显着评价。在分散体中，4c、4f和4g对枯草芽孢杆菌B29、大肠杆菌E266这三种微生物的抗菌活性最高，抑菌圈分别为21、19和19 mm。化合物4a、4c、4h对A.niger、Fusarium oxysporum真菌菌株表现出良好的抗真菌活性。此外，使用来自金黄色葡萄球菌的 C(30) 类胡萝卜素脱氢角鲨烯合酶与双膦酸盐 BPH-700 复合的晶体结构进行了蛋白质配体相互作用的分子对接。最终化合物中，4e、4g 和 4h 分别显示出最高的结合能 ΔG = -7.89、-7.48 和 -7.08 Kcal/mol，以及氨基酸相互作用 Lys273、Asp27。