D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid | 15813-34-0

• 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
• 英文名称: D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid
• 英文别名: racem.-2.3-bis-(3.4-dimethoxy-benzyl)-succinic acid；racem.-2.3-Bis-(3.4-dimethoxy-benzyl)-bernsteinsaeure；(2S,3S)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butanedioic acid
• CAS: 15813-34-0；15905-29-0；93609-04-2；126965-32-0
• 化学式: C₂₂H₂₆O₈
• 分子量: 418.444
• InChiKey: NCLKBTXJCZVFDN-HOTGVXAUSA-N

物化性质

• 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：

  D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid 反应 0.33h， 生成 D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid anhydride
  参考文献：
  名称：

  Dicaffeoyltartaric Acid Analogues Inhibit Human Immunodeficiency Virus Type 1 (HIV-1) Integrase and HIV-1 Replication at Nontoxic Concentrations

  摘要：

  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.

  DOI：

  10.1021/jm010359d
• 作为产物：
  描述：

  2-(3,4-dimethoxybenzylidene)butanedioic acid monoethyl ester 在 盐酸 、 sodium hydroxide 、 硫酸 、 potassium tert-butylate 、 氢气 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 31.0h， 生成 D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid
  参考文献：
  名称：

  由内消旋酸酐不对称合成木脂素内酯

  摘要：

  给出了内消旋-2,3-二苄基丁二酸酐的合成。该化合物与（+）-α-甲基苄基胺的反应非对映选择性地进行，得到丁二酸单酰胺，其转化为对映体富集的顺式-2，3-二苄基丁内酯木脂素。

  DOI：

  10.1016/0040-4020(96)00761-2

文献信息

• 36. The constituents of natural phenolic resins. Part XIV. The synthesis of dl-, d-, and l-matairesinol dimethyl ether
  作者：Robert D. Haworth、David Woodcock

  DOI：10.1039/jr9390000154

  日期：——
• Crystalline constituents of euphorbiaceae—VI
  作者：L.R. Row、P. Satyanarayana、G.S.R.Subba Rao

  DOI：10.1016/s0040-4020(01)82594-1

  日期：1967.1
• Asymmetric synthesis of a lignan lactone from a meso anhydride
  作者：Robert S. Ward、Andrew Pelter、Mark I. Edwards、Jeremy Gilmore

  DOI：10.1016/0040-4020(96)00761-2

  日期：1996.9

  The synthesis of a meso-2,3-dibenzylbutanedioic acid anhydride is given. Reaction of this with (+)-α-methylbenzylamine proceeds diastereoselectively to give a butanedioic acid monoamide which is converted into an enantiomerically enriched cis-2,3-dibenzylbutyrolactone lignan.

  给出了内消旋-2,3-二苄基丁二酸酐的合成。该化合物与（+）-α-甲基苄基胺的反应非对映选择性地进行，得到丁二酸单酰胺，其转化为对映体富集的顺式-2，3-二苄基丁内酯木脂素。
• 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.