3,4-Bis(3,4-dimethoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid | 653572-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,4-Bis(3,4-dimethoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid
• CAS: 653572-64-6
• 化学式: C₂₂H₂₁NO₈
• 分子量: 427.411
• InChiKey: MVQHJMRXUZQUSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-Bis(3,4-dimethoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid 在 sodium hypochlorite 、 sodium hydrogensulfite 作用下， 以78%的产率得到3,4-bis(3,4-dimethoxyphenyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Catechol-Substituted l -Chicoric acid analogues as HIV integrase inhibitors

  摘要：

  HIV integrase catalyzes the integration of HIV DNA copy into the host cell DNA, which is essential for the production of progeny viruses. L-Chicoric acid and dicaffeoylquinic acids, isolated from plants, are well known potent inhibitors of HIV integrase. The common structural features of these inhibitors are caffeic acid derivatives connected to tartaric acid or quinic acid through ester bonds. In the present study, we have synthesized and tested the inhibitory activities of a new type of HIV IN inhibitors, which has catechol groups in place of caffeoyl groups in the structure of L-chicoric acid. Upon substitution of catechol groups at succinic acid, pyrrol dicarboxylic acid, maleimide or maleic anhydride, the inhibitory activities (IC50 = 3.8-23.6 muM) were retained or remarkably increased when compared to parent compound L-chicoric acid (IC50 = 13.7 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.046
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)丙酮酸 在 正丁基锂 、 氨 、 四氯化钛 作用下， 以 四氢呋喃 为溶剂， 生成 3,4-Bis(3,4-dimethoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid
  参考文献：
  名称：

  Catechol-Substituted l -Chicoric acid analogues as HIV integrase inhibitors

  摘要：

  HIV integrase catalyzes the integration of HIV DNA copy into the host cell DNA, which is essential for the production of progeny viruses. L-Chicoric acid and dicaffeoylquinic acids, isolated from plants, are well known potent inhibitors of HIV integrase. The common structural features of these inhibitors are caffeic acid derivatives connected to tartaric acid or quinic acid through ester bonds. In the present study, we have synthesized and tested the inhibitory activities of a new type of HIV IN inhibitors, which has catechol groups in place of caffeoyl groups in the structure of L-chicoric acid. Upon substitution of catechol groups at succinic acid, pyrrol dicarboxylic acid, maleimide or maleic anhydride, the inhibitory activities (IC50 = 3.8-23.6 muM) were retained or remarkably increased when compared to parent compound L-chicoric acid (IC50 = 13.7 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.046

文献信息

• Catechol-Substituted l -Chicoric acid analogues as HIV integrase inhibitors
  作者：Jae Yeol Lee、Kwon Joong Yoon、Yong Sup Lee

  DOI：10.1016/j.bmcl.2003.09.046

  日期：2003.12

  HIV integrase catalyzes the integration of HIV DNA copy into the host cell DNA, which is essential for the production of progeny viruses. L-Chicoric acid and dicaffeoylquinic acids, isolated from plants, are well known potent inhibitors of HIV integrase. The common structural features of these inhibitors are caffeic acid derivatives connected to tartaric acid or quinic acid through ester bonds. In the present study, we have synthesized and tested the inhibitory activities of a new type of HIV IN inhibitors, which has catechol groups in place of caffeoyl groups in the structure of L-chicoric acid. Upon substitution of catechol groups at succinic acid, pyrrol dicarboxylic acid, maleimide or maleic anhydride, the inhibitory activities (IC50 = 3.8-23.6 muM) were retained or remarkably increased when compared to parent compound L-chicoric acid (IC50 = 13.7 muM). (C) 2003 Elsevier Ltd. All rights reserved.