4',5'-bis(benzyloxy)-2'-hydroxyacetophenone | 7298-39-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4',5'-bis(benzyloxy)-2'-hydroxyacetophenone
• 英文别名: 4,5-bis(benzyloxy)-2-hydroxyacetophenone；2-hydroxy-4,5-dibenzyloxyacetophenone；4,5-dibenzyloxy-2-hydroxyacetophenone；2-Hydroxy-4,5-dibenzyloxyacetophenon；4,5-Dibenzyloxy-2-hydroxyacetophenon；1-[2-Hydroxy-4,5-bis(phenylmethoxy)phenyl]ethanone
• CAS: 7298-39-7
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: PKTOUVSBSOBPDB-UHFFFAOYSA-N

物化性质

• 熔点：
  96–97°C
• 沸点：
  534.0±45.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4',5'-bis(benzyloxy)-2'-hydroxyacetophenone 在 氢氧化钾 、 sodium hydroxide 、 双氧水 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 78.0h， 生成 2',4',5'-tribenzyloxy-3,4-dimethoxychalkone epoxide
  参考文献：
  名称：

  Bhardwaj, D. K.; Bisht, M. S.; Jain, R. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 1, p. 82 - 84

  摘要：

  DOI：
• 作为产物：
  描述：

  2′,4′,5′-三甲氧基苯乙酮 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 氯苯 、 丙酮 为溶剂， 反应 17.17h， 生成 4',5'-bis(benzyloxy)-2'-hydroxyacetophenone
  参考文献：
  名称：

  Antimalarial activity of HIV-1 protease inhibitor in chromone series

  摘要：

  Increasing parasite resistance to nearly all available antimalarial drugs becomes a serious problem to human health and necessitates the need to continue the search for new effective drugs. Recent studies have shown that clinically utilized HIV-1 protease (HIV-1 PR) inhibitors can inhibit the in vitro and in vivo growth of Plasmodium falciparum. In this study, a series of chromone derivatives possessing HIV-1 PR inhibitory activity has been tested for antimalarial activity against P. falciparum (K1 multi-drug resistant strain). Chromone 15, the potent HIV-1 PR inhibitor (IC50 = 0.65 mu M), was found to be the most potent antimalarial compound with IC50 = 0.95 mu M while primaquine and tafenoquine showed IC50 = 2.41 and 1.95 mu M, respectively. Molecular docking study of chromone compounds against plasmepsin II, an aspartic protease enzyme important in hemoglobin degradation, revealed that chromone 15 exhibited the higher binding affinity (binding energy = -13.24 kcal/mol) than the known PM II inhibitors. Thus, HIV-1 PR inhibitor in chromone series has the potential to be a new class of antimalarial agent. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.10.006

文献信息

• Obtusastyrene and obtustyrene, cinnamylphenols from Dalbergia retusa
  作者：Michael Gregson、W.David Ollis、Brian T. Redman、Ian O. Sutherland、H.H. Dietrichs、Otto R. Gottlieb

  DOI：10.1016/s0031-9422(00)94596-5

  日期：1978.1
• Camarda, Lorenzo; Merlini, Lucio; Nasini, Gianluca, Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 289 - 292
  作者：Camarda, Lorenzo、Merlini, Lucio、Nasini, Gianluca

  DOI：——

  日期：——
• Bhardwaj, D. K.; Gupta, A. K.; Jain, R. K., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 6, p. 446 - 448
  作者：Bhardwaj, D. K.、Gupta, A. K.、Jain, R. K.、Munjal, Anita

  DOI：——

  日期：——