7-(3-Benzimidazolyl-2-hydroxypropoxy)-4-methylchromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(3-Benzimidazolyl-2-hydroxypropoxy)-4-methylchromen-2-one
• 英文别名: 7-[3-(benzimidazol-1-yl)-2-hydroxypropoxy]-4-methylchromen-2-one
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: XGYWFNBUMDLLLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  羟甲香豆素 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 7-(3-Benzimidazolyl-2-hydroxypropoxy)-4-methylchromen-2-one
  参考文献：
  名称：

  Synthesis and bioactive evaluation of a novel series of coumarinazoles

  摘要：

  A series of novel coumarinazoles were designed, synthesized, and characterized by IR, NMR, MS and HRMS spectra. The bioactive assay for the newly prepared compounds against six bacteria and five fungi manifested that most new compounds exhibited good or even stronger antibacterial and antifungal activities in comparison with reference drugs Chloromycin, Norfloxacin and Fluconazole. Bis-azole alcohols 7a and 7d-e showed better anti-Candida utilis activity than mono-azole derivatives 4a and 4d-e at the tested concentrations, and they were more potent than the clinical Fluconazole. While triazole alcohol 7a gave comparable anti-Candida albicans and anti-Candida mycoderma activity to Fluconazole and better anti-MRSA activity than mono-triazole one 4a and clinical Norfloxacin. 1H-Benzoimidazol-2-ylthio coumarin derivatives 4e and 7e gave the strongest anti-Escherichia coli JM109 efficacy. Oxiran-2-ylmethoxy moiety was found to be a beneficial fragment to improve antibacterial and antifungal activity to some extent. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.029

文献信息

• Synthesis and bioactive evaluation of a novel series of coumarinazoles
  作者：Guri L.V. Damu、Sheng-Feng Cui、Xin-Mei Peng、Qin-Mei Wen、Gui-Xin Cai、Cheng-He Zhou

  DOI：10.1016/j.bmcl.2014.05.029

  日期：2014.8

  A series of novel coumarinazoles were designed, synthesized, and characterized by IR, NMR, MS and HRMS spectra. The bioactive assay for the newly prepared compounds against six bacteria and five fungi manifested that most new compounds exhibited good or even stronger antibacterial and antifungal activities in comparison with reference drugs Chloromycin, Norfloxacin and Fluconazole. Bis-azole alcohols 7a and 7d-e showed better anti-Candida utilis activity than mono-azole derivatives 4a and 4d-e at the tested concentrations, and they were more potent than the clinical Fluconazole. While triazole alcohol 7a gave comparable anti-Candida albicans and anti-Candida mycoderma activity to Fluconazole and better anti-MRSA activity than mono-triazole one 4a and clinical Norfloxacin. 1H-Benzoimidazol-2-ylthio coumarin derivatives 4e and 7e gave the strongest anti-Escherichia coli JM109 efficacy. Oxiran-2-ylmethoxy moiety was found to be a beneficial fragment to improve antibacterial and antifungal activity to some extent. (C) 2014 Elsevier Ltd. All rights reserved.