(E)-4-methoxybenzyl 3-(3,4-dihydroxyphenyl)acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-methoxybenzyl 3-(3,4-dihydroxyphenyl)acrylate
• 英文别名: (4-methoxyphenyl)methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: QFIPDXXDDBFRAP-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-4-methoxybenzyl 3-(3,4-dihydroxyphenyl)acrylate 在 manganese triacetate 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以25.2%的产率得到bis(4-methoxybenzyl)-6,9,10-trihydroxybenzo[k,l]xanthene-1,2-dicarboxylate
  参考文献：
  名称：

  Bioinspired benzoxanthene lignans as a new class of antimycotic agents: synthesis and Candida spp. growth inhibition

  摘要：

  In this work we synthetized the bioinspired benzoxanthene lignans (BXLs)3,14-22, and the phenazine derivative23as potential antimycotic agents. MICs and MFCs againstCandidastrains were determined. In a preliminary screening, compounds3,15,20,21,22were substantially inactive. Compounds14and17showed antifungal activity, being able to inhibit the growth of the majority ofCandidastrains with MIC values in the range 4.6-19.2 mu M (14) and 26.0-104.3 mu M (17); for three strains, the MICs were lower than those obtained using the antimycotic drug fluconazole. The three BXLs18,19and23showed some MIC values lower than that of fluconazole;18was also active against two non-albicans Candidastrains resistant to fluconazole. Phenazine23, although active only against one strain (MIC = 1.3 mu M), was one order of magnitude more potent than fluconazole. All the BXLs were fungicidal.

  DOI：

  10.1080/14786419.2018.1525375
• 作为产物：
  描述：

  咖啡酸 、 4-甲氧基苄醇 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.17h， 以35.3%的产率得到(E)-4-methoxybenzyl 3-(3,4-dihydroxyphenyl)acrylate
  参考文献：
  名称：

  Bioinspired benzoxanthene lignans as a new class of antimycotic agents: synthesis and Candida spp. growth inhibition

  摘要：

  In this work we synthetized the bioinspired benzoxanthene lignans (BXLs)3,14-22, and the phenazine derivative23as potential antimycotic agents. MICs and MFCs againstCandidastrains were determined. In a preliminary screening, compounds3,15,20,21,22were substantially inactive. Compounds14and17showed antifungal activity, being able to inhibit the growth of the majority ofCandidastrains with MIC values in the range 4.6-19.2 mu M (14) and 26.0-104.3 mu M (17); for three strains, the MICs were lower than those obtained using the antimycotic drug fluconazole. The three BXLs18,19and23showed some MIC values lower than that of fluconazole;18was also active against two non-albicans Candidastrains resistant to fluconazole. Phenazine23, although active only against one strain (MIC = 1.3 mu M), was one order of magnitude more potent than fluconazole. All the BXLs were fungicidal.

  DOI：

  10.1080/14786419.2018.1525375

文献信息

• Bioinspired benzoxanthene lignans as a new class of antimycotic agents: synthesis and <i>Candida</i> spp. growth inhibition
  作者：Carlo Genovese、Luana Pulvirenti、Nunzio Cardullo、Vera Muccilli、Gianna Tempera、Daria Nicolosi、Corrado Tringali

  DOI：10.1080/14786419.2018.1525375

  日期：2020.6.17

  In this work we synthetized the bioinspired benzoxanthene lignans (BXLs)3,14-22, and the phenazine derivative23as potential antimycotic agents. MICs and MFCs againstCandidastrains were determined. In a preliminary screening, compounds3,15,20,21,22were substantially inactive. Compounds14and17showed antifungal activity, being able to inhibit the growth of the majority ofCandidastrains with MIC values in the range 4.6-19.2 mu M (14) and 26.0-104.3 mu M (17); for three strains, the MICs were lower than those obtained using the antimycotic drug fluconazole. The three BXLs18,19and23showed some MIC values lower than that of fluconazole;18was also active against two non-albicans Candidastrains resistant to fluconazole. Phenazine23, although active only against one strain (MIC = 1.3 mu M), was one order of magnitude more potent than fluconazole. All the BXLs were fungicidal.