2,3-双[(3,4-二甲氧基苯基)甲基]丁二酸 | 93609-04-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 中文名称: 2,3-双[(3,4-二甲氧基苯基)甲基]丁二酸
• 英文名称: meso-2,3-Bis-(3,4-dimethoxy-benzyl)-bernsteinsaeure
• 英文别名: 2,3-bis(3,4-dimethoxybenzyl)succinic acid；2,3-bis[(3,4-dimethoxyphenyl)methyl]butanedioic acid
• CAS: 93609-04-2
• 化学式: C₂₂H₂₆O₈
• 分子量: 418.444
• InChiKey: NCLKBTXJCZVFDN-UHFFFAOYSA-N

物化性质

• 熔点：
  223-224 °C
• 沸点：
  533.4±45.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3-双[(3,4-二甲氧基苯基)甲基]丁二酸 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到meso-2,3-bis(3,4-dihydroxybenzyl)succinic 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
• 作为产物：
  描述：

  3,4-二甲氧基苯丙酸 在 lithium diisopropyl amide 、 碘 作用下， 以 四氢呋喃 为溶剂， 以47%的产率得到2,3-双[(3,4-二甲氧基苯基)甲基]丁二酸
  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

• Neelima; Bhaduri, A. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 3, p. 209 - 215
  作者：Neelima、Bhaduri, A. P.

  DOI：——

  日期：——
• Traverso,G., Gazzetta Chimica Italiana, 1960, vol. 90, p. 792 - 807
  作者：Traverso,G.

  DOI：——

  日期：——
• Dicaffeoyltartaric Acid Analogues Inhibit Human Immunodeficiency Virus Type 1 (HIV-1) Integrase and HIV-1 Replication at Nontoxic Concentrations
  作者：Ryan A. Reinke、Peter J. King、Joseph G. Victoria、Brenda R. McDougall、Guoxiang Ma、Yingqun Mao、Manfred G. Reinecke、W. Edward Robinson

  DOI：10.1021/jm010359d

  日期：2002.8.1

  The human immunodeficiency virus type 1 (HIV-1) is a major health problem worldwide. In this study, 17 analogues of L-chicoric acid, a potent inhibitor of HIV integrase were studied. Of these analogues, five submicromolar inhibitors of integrase were discovered and 13 compounds with activity against integrase at less than 10 muM were identified. Six demonstrated greater than 10-fold selectivity for HIV replication over cellular toxicity. Ten analogues inhibited HIV replication at nontoxic concentrations. Alteration of the linkages between the two bis-catechol rings, including the use of amides, mixed amide esters, cholate, and alkyl bridges, was explored. Amides were as active as esters but were more toxic in tissue culture. Alkyl and cholate bridges were significantly less potent against HIV-1 integrase in vitro and were inactive against HIV-1 replication. Two amino acid derivates and one digalloylderivative of L-chicoric acid (L-CA) showed improved selectivity over L-CA against integration in cell culture. These data suggest that in addition to the bis-catechols and free carboxylic acid groups reported previously, polar linkages are important constituents for optimal activity against HIV-1 integrase and that new derivatives can be developed with increased specificity for integration over HIV entry in vivo.
• 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.