6-Bromo-4-(6-bromo-5-ethoxycarbonyl-7-methoxy-1,3-benzodioxol-4-yl)-7-methoxy-1,3-benzodioxole-5-carboxylic acid | 166186-31-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 6-Bromo-4-(6-bromo-5-ethoxycarbonyl-7-methoxy-1,3-benzodioxol-4-yl)-7-methoxy-1,3-benzodioxole-5-carboxylic acid
• CAS: 166186-31-8
• 化学式: C₂₀H₁₆Br₂O₁₀
• 分子量: 576.149
• InChiKey: SNHJAKDHLATPGY-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：
  119
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-Bromo-4-(6-bromo-5-ethoxycarbonyl-7-methoxy-1,3-benzodioxol-4-yl)-7-methoxy-1,3-benzodioxole-5-carboxylic acid 在 氯化亚砜 作用下， 生成 ethyl 2'-chlorocarbonyl-3,3'-dibromo-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate
  参考文献：
  名称：

  A solid-phase approach to DDB derivatives

  摘要：

  Since the discovery of 2,2'-dimethoxycarbonyl-4,4-dimethoxy-5,6,5',6'-biomethylenedioxy-biphenyl (DDB) as a potent anti-HBV agent, we have studied the structure-activity relationships of 4,4'-dimethoxy -5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-(4- substituted benzyl piperazin-1-yl)carbonyl-biphenyl as anti-HBV agents. Therefore, it is rational to extend this study to the 3,3'-disustituted-4,4'-dimethoxy5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-Serine derivatives. Thus, in an attempt to develop an efficient method for the preparation of a large number of DDB derivatives, the reaction between a DDB acid chloride and serine derivatives on solid support was studied. The structure of resulted compounds was confirmed by LC-MS and H-1 NMR analysis. Compounds 2a, 2d, 2f, 2j showed in vitro anti-HBV activity without significant toxicity up to 100 mu M. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.03.024
• 作为产物：
  描述：

  联苯双酯 在 氢氧化钾 、 溴 、 乙酸酐 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 103.5h， 生成 6-Bromo-4-(6-bromo-5-ethoxycarbonyl-7-methoxy-1,3-benzodioxol-4-yl)-7-methoxy-1,3-benzodioxole-5-carboxylic acid
  参考文献：
  名称：

  Anti-AIDS (Acquired Immune Deficiency Syndrome) Agents. 17. New Brominated Hexahydroxybiphenyl Derivatives as Potent Anti-HIV Agents

  摘要：

  Sixteen biphenyl derivatives were synthesized and evaluated for their inhibitory activity against HIV-1 replication in acutely infected H9 cells. 3-Bromo- (4) and 3,3'-dibromo-4,4'-dimethoxy-5,6,5',6'-bis(methylenedioxy)-2,2' -bis(methoxycarbonyl)biphenyl (5) demonstrated potent anti-HIV activity with EC(50) values of 0.52 and 0.23 mu g/mL and therapeutic index values of > 190 and > 480, respectively. A comparison, of the anti-HIV activity of these biphenyl derivatives suggested that the types of substituents on the phenolic hydroxy groups rather than the number of bromine(s) on the aromatic rings are important to the enhanced anti-HIV activity. Compounds 4 and 5 also showed potent inhibitory activity against HIV-1 reverse transcriptase in a template-primer dependent manner. The site of inhibition of HIV could be related to inhibition of this enzyme. Compounds 4 and 5 did not induce virus expression from the chronic HIV-1-infected cell lines ACH-2 and U1. Furthermore, these two agents did not inhibit an increase in virus production from the chronic HIV-1-infected cell lines when the phorbol ester PMA was present.

  DOI：

  10.1021/jm00016a002

文献信息

• Anti-AIDS (Acquired Immune Deficiency Syndrome) Agents. 17. New Brominated Hexahydroxybiphenyl Derivatives as Potent Anti-HIV Agents
  作者：Lan Xie、Jing-Xi Xie、Yoshiki Kashiwada、L. Mark Cosentino、Shwu-Huey Liu、Rekha B. Pai、Yung-Chi Cheng、Kuo-Hsiung Lee

  DOI：10.1021/jm00016a002

  日期：1995.8

  Sixteen biphenyl derivatives were synthesized and evaluated for their inhibitory activity against HIV-1 replication in acutely infected H9 cells. 3-Bromo- (4) and 3,3'-dibromo-4,4'-dimethoxy-5,6,5',6'-bis(methylenedioxy)-2,2' -bis(methoxycarbonyl)biphenyl (5) demonstrated potent anti-HIV activity with EC(50) values of 0.52 and 0.23 mu g/mL and therapeutic index values of > 190 and > 480, respectively. A comparison, of the anti-HIV activity of these biphenyl derivatives suggested that the types of substituents on the phenolic hydroxy groups rather than the number of bromine(s) on the aromatic rings are important to the enhanced anti-HIV activity. Compounds 4 and 5 also showed potent inhibitory activity against HIV-1 reverse transcriptase in a template-primer dependent manner. The site of inhibition of HIV could be related to inhibition of this enzyme. Compounds 4 and 5 did not induce virus expression from the chronic HIV-1-infected cell lines ACH-2 and U1. Furthermore, these two agents did not inhibit an increase in virus production from the chronic HIV-1-infected cell lines when the phorbol ester PMA was present.
• A solid-phase approach to DDB derivatives
  作者：Xiuxiang Qi、Xiaolai Wang、Limin Wang、Qiang Wang、Senxiang Cheng、Jishuan Suo、Junbiao Chang

  DOI：10.1016/j.ejmech.2005.03.024

  日期：2005.8

  Since the discovery of 2,2'-dimethoxycarbonyl-4,4-dimethoxy-5,6,5',6'-biomethylenedioxy-biphenyl (DDB) as a potent anti-HBV agent, we have studied the structure-activity relationships of 4,4'-dimethoxy -5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-(4- substituted benzyl piperazin-1-yl)carbonyl-biphenyl as anti-HBV agents. Therefore, it is rational to extend this study to the 3,3'-disustituted-4,4'-dimethoxy5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-Serine derivatives. Thus, in an attempt to develop an efficient method for the preparation of a large number of DDB derivatives, the reaction between a DDB acid chloride and serine derivatives on solid support was studied. The structure of resulted compounds was confirmed by LC-MS and H-1 NMR analysis. Compounds 2a, 2d, 2f, 2j showed in vitro anti-HBV activity without significant toxicity up to 100 mu M. (c) 2005 Elsevier SAS. All rights reserved.