Methyl 6-bromo-4-(7-bromo-4-methoxy-6-methoxycarbonyl-1,3-benzodioxol-5-yl)-7-methoxy-1,3-benzodioxole-5-carboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: Methyl 6-bromo-4-(7-bromo-4-methoxy-6-methoxycarbonyl-1,3-benzodioxol-5-yl)-7-methoxy-1,3-benzodioxole-5-carboxylate
• 化学式: C₂₀H₁₆Br₂O₁₀
• 分子量: 576.149
• InChiKey: IVLCRRAITFTQOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  dimethyl 7,4'-dimethoxy-[4,5']bi[1,3-benzodioxolyl]-5,6'-dicarboxylate 在 溴 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以82%的产率得到Methyl 6-bromo-4-(7-bromo-4-methoxy-6-methoxycarbonyl-1,3-benzodioxol-5-yl)-7-methoxy-1,3-benzodioxole-5-carboxylate
  参考文献：
  名称：

  Anti-aids agents—XXVI. Structure-activity correlations of Gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues

  摘要：

  Bioactivity-directed fractionation of an ethanolic extract of the stems of Kadsura interior led to the isolation and identification of 12 known lignans (1-12). Seven of these compounds (1, 6, 8-12) were active as anti-HIV agents. Gomisin-G (11) exhibited the most potent anti-HIV activity with EC50 and therapeutic index (TI) Values of 0.006 mu g/mL and 300, respectively. Schisantherin-D (6), kadsuranin (8), and schisandrin-C (10) showed good activity with EC50 values of 0.5, 0.8, and 1.2 mu g/mL, and TI values of 110, 56, and 33.3, respectively. Ten related synthetic biphenyl compounds, five variously substituted bismethylenedioxy, dimethoxy, and dimethoxycarbonyl isomers (18-22) and five brominated derivatives (23-27) also were evaluated for inhibitory activity against HIV-1 replication in acutely infected H9 cells. The total syntheses of two new isomers (21 and 22) are reported for the first time. The anti-HIV data indicated that the relative position and types of substituents on the phenolic hydroxy groups of either the natural lignans or the synthetic biphenyl compounds rather than the numbers of bromine(s) on the aromatic rings art of primary importance. In the cyclooctane ring of the natural lignans, the position and substitution of hydroxy groups are also important to enhanced anti-HIV activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00118-1

文献信息

• Anti-aids agents—XXVI. Structure-activity correlations of Gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues
  作者：Dao-Feng Chen、Shun-Xiang Zhang、Lan Xie、Jing-Xi Xie、Ke Chen、Yoshiki Kashiwada、Bing-Nan Zhou、Pei Wang、L.Mark Cosentino、Kuo-Hsiung Lee

  DOI：10.1016/s0968-0896(97)00118-1

  日期：1997.8

  Bioactivity-directed fractionation of an ethanolic extract of the stems of Kadsura interior led to the isolation and identification of 12 known lignans (1-12). Seven of these compounds (1, 6, 8-12) were active as anti-HIV agents. Gomisin-G (11) exhibited the most potent anti-HIV activity with EC50 and therapeutic index (TI) Values of 0.006 mu g/mL and 300, respectively. Schisantherin-D (6), kadsuranin (8), and schisandrin-C (10) showed good activity with EC50 values of 0.5, 0.8, and 1.2 mu g/mL, and TI values of 110, 56, and 33.3, respectively. Ten related synthetic biphenyl compounds, five variously substituted bismethylenedioxy, dimethoxy, and dimethoxycarbonyl isomers (18-22) and five brominated derivatives (23-27) also were evaluated for inhibitory activity against HIV-1 replication in acutely infected H9 cells. The total syntheses of two new isomers (21 and 22) are reported for the first time. The anti-HIV data indicated that the relative position and types of substituents on the phenolic hydroxy groups of either the natural lignans or the synthetic biphenyl compounds rather than the numbers of bromine(s) on the aromatic rings art of primary importance. In the cyclooctane ring of the natural lignans, the position and substitution of hydroxy groups are also important to enhanced anti-HIV activity. (C) 1997 Elsevier Science Ltd.