5-(3,4-Dihydroxy-phenyl)-6,7-dimethyl-naphthalene-2,3-diol | 741292-76-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 5-(3,4-Dihydroxy-phenyl)-6,7-dimethyl-naphthalene-2,3-diol
• 英文别名: 5-(3,4-dihydroxyphenyl)-6,7-dimethylnaphthalene-2,3-diol
• CAS: 741292-76-2
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: XWOVUBPUCSLBNM-UHFFFAOYSA-N

物化性质

• 熔点：
  244-245 °C
• 沸点：
  526.5±50.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  80.92
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  二氯甲烷 、 5-(3,4-Dihydroxy-phenyl)-6,7-dimethyl-naphthalene-2,3-diol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以55%的产率得到2,3-Dimethyl-1-(3,4-methylenedioxyphenyl)-(6,7-methylenedioxy)naphthalene
  参考文献：
  名称：

  Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans

  摘要：

  Ten lignans (2-11) and a series of azalignans including 1-aryl-pyrronaphthalenes 20-24 and 3-N-alkylaminomethyl-1-arylnaphthalenes 25-28, structurally related to two HIV reverse transcriptase inhibitors, retrojusticidin B and phyllamyricin A, were prepared from phyllanthin (1) for evaluation of anti-HIV activities. Anti-HIV activity of these compounds on a R5 pseudotype virus, ConB/pNL43E-L+, in the U87-CD4-CCR5 cells has been measured. Compounds 5, 22, 23, and 28 showed good anti-HIV activity with IC50 value of 0.25, 1.07, 0.01, 0.32 mug/mL, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.036
• 作为产物：
  描述：

  1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalene 在 吡啶盐酸盐 作用下， 反应 0.5h， 以57%的产率得到5-(3,4-Dihydroxy-phenyl)-6,7-dimethyl-naphthalene-2,3-diol
  参考文献：
  名称：

  Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans

  摘要：

  Ten lignans (2-11) and a series of azalignans including 1-aryl-pyrronaphthalenes 20-24 and 3-N-alkylaminomethyl-1-arylnaphthalenes 25-28, structurally related to two HIV reverse transcriptase inhibitors, retrojusticidin B and phyllamyricin A, were prepared from phyllanthin (1) for evaluation of anti-HIV activities. Anti-HIV activity of these compounds on a R5 pseudotype virus, ConB/pNL43E-L+, in the U87-CD4-CCR5 cells has been measured. Compounds 5, 22, 23, and 28 showed good anti-HIV activity with IC50 value of 0.25, 1.07, 0.01, 0.32 mug/mL, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.036

文献信息

• Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans
  作者：Kadali S Sagar、Chia-Chuan Chang、Wei-Kung Wang、Jung-Yaw Lin、Shoei-Sheng Lee

  DOI：10.1016/j.bmc.2004.05.036

  日期：2004.8

  Ten lignans (2-11) and a series of azalignans including 1-aryl-pyrronaphthalenes 20-24 and 3-N-alkylaminomethyl-1-arylnaphthalenes 25-28, structurally related to two HIV reverse transcriptase inhibitors, retrojusticidin B and phyllamyricin A, were prepared from phyllanthin (1) for evaluation of anti-HIV activities. Anti-HIV activity of these compounds on a R5 pseudotype virus, ConB/pNL43E-L+, in the U87-CD4-CCR5 cells has been measured. Compounds 5, 22, 23, and 28 showed good anti-HIV activity with IC50 value of 0.25, 1.07, 0.01, 0.32 mug/mL, respectively. (C) 2004 Elsevier Ltd. All rights reserved.