7-(2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propoxy)-4-methyl-2H-chromen-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-(2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propoxy)-4-methyl-2H-chromen-2-one
• 英文别名: 7-[2-Hydroxy-3-(1,2,4-triazol-1-yl)propoxy]-4-methylchromen-2-one
• 化学式: C₁₅H₁₅N₃O₄
• 分子量: 301.302
• InChiKey: GDCFJOBMRMVPAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  6

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-(2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propoxy)-4-methyl-2H-chromen-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

• Coumarin-derived azolyl ethanols: synthesis, antimicrobial evaluation and preliminary action mechanism
  作者：Xin-Mei Peng、Kannekanti Vijaya Kumar、Guri L.V. Damu、Cheng-He Zhou

  DOI：10.1007/s11426-015-0351-0

  日期：2016.7

  found that compound 14 could interact with calf thymus DNA by groove binding to form 14-DNA complex via both hydrogen bonds and van der Waals force, which might be the factor to exert the powerful antimicrobial activity.

  方便地合成了一系列香豆素衍生的偶氮基乙醇，包括咪唑基，三唑基，四唑基，苯并三唑基，巯基-咪唑基和巯基-三唑基，并通过IR，1 H NMR，13 C NMR和高分辨率质谱（HRMS）光谱进行了表征。。一些制备的化合物显示出适当的logPow值以及有效的抗菌和抗真菌活性。值得注意的是，化合物14双三唑基乙醇基团对MRSA的最低最低抑菌浓度（MIC）值低至8 mg / mL，与参考药物诺氟沙星（MIC = 8 mg / mL）和氯霉素（MIC = 16 mg / mL）相当甚至更好）。与氟康唑相比，它还可以有效抑制被测真菌菌株的生长。通过UV-Vis吸收和荧光光谱研究香豆素14与小牛胸腺DNA的进一步结合研究。发现化合物14可以通过氢键和范德华力通过凹槽结合与小牛胸腺DNA相互作用而形成14 -DNA复合物，这可能是发挥强大的抗菌活性的因素。