5-[双(3-羧基-4-羟基苯基)甲基]-2-羟基苯甲酸 | 129749-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 5-[双(3-羧基-4-羟基苯基)甲基]-2-羟基苯甲酸
• 英文名称: 3,3',3''-tricarboxy-4,4',4''-trihydroxytriphenylmethane
• 英文别名: ATA fraction 8, ammonium salt；5-[bis(3-carboxy-4-hydroxyphenyl)methyl]-2-hydroxybenzoic acid
• CAS: 129749-38-8
• 化学式: C₂₂H₁₆O₉
• 分子量: 424.364
• InChiKey: WDHMZEQRWAWXPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  173
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-[双(3-羧基-4-羟基苯基)甲基]-2-羟基苯甲酸 、 重氮甲烷 以 乙醚 为溶剂， 反应 24.0h， 以76%的产率得到3,3',3''-tricarbomethoxy-4,4',4''-trihydroxytriphenylmethane
  参考文献：
  名称：

  Synthesis and anti-HIV activities of low molecular weight aurintricarboxylic acid fragments and related compounds

  摘要：

  Several compounds corresponding to fragments of the schematic representation of the polymeric structure of aurintricarboxylic acid (ATA) have been prepared and tested for prevention of the cytopathic effect of HIV-1 and HIV-2 in MT-4 cell culture and HIV-1 in CEM cell culture. Both the triphenylcarbinol 3 as well as the triphenylmethane 5 were found to afford protection against the cytopathogenicity of HIV-2 in MT-4 cells and HIV-1 in CEM cells, but they were inactive against HIV-1 in MT-4 cells. Both substances were also found to inhibit syncytium formation when MOLT-4 cells were cocultured with HIV-2-infected HUT-78 cells, but were inactive in this assay against HIV-1-infected cells. When observed, the activity is generally moderate in degree of protection and requires concentrations in the 10(-4) molar range. In contrast to ATA, both of these substances were inactive when tested for prevention of the binding of the OKT4A monoclonal antibody to the CD4 receptor and also for inhibition of HIV-1 reverse transcriptase. These substances therefore appear act by a mechanism that is distinct from that of polymeric ATA. Several active and inactive structural analogues of 3 and 5 were also synthesized. The anti-HIV activity in this series seems to depend on the presence of anionic carboxylate groups, since the methyl esters 4, 6, and 12 were uniformly inactive. The diphenylmethanes 8, 14, 18, and 19 also reproducibly inhibited the cytopathic effect of HIV-1 in CEM cell culture.

  DOI：

  10.1021/jm00105a053
• 作为产物：
  描述：

  5-[双(3-羧基-4-羟基苯基)-羟甲基]-2-羟基苯甲酸 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以98%的产率得到5-[双(3-羧基-4-羟基苯基)甲基]-2-羟基苯甲酸
  参考文献：
  名称：

  Synthesis and anti-HIV activities of low molecular weight aurintricarboxylic acid fragments and related compounds

  摘要：

  Several compounds corresponding to fragments of the schematic representation of the polymeric structure of aurintricarboxylic acid (ATA) have been prepared and tested for prevention of the cytopathic effect of HIV-1 and HIV-2 in MT-4 cell culture and HIV-1 in CEM cell culture. Both the triphenylcarbinol 3 as well as the triphenylmethane 5 were found to afford protection against the cytopathogenicity of HIV-2 in MT-4 cells and HIV-1 in CEM cells, but they were inactive against HIV-1 in MT-4 cells. Both substances were also found to inhibit syncytium formation when MOLT-4 cells were cocultured with HIV-2-infected HUT-78 cells, but were inactive in this assay against HIV-1-infected cells. When observed, the activity is generally moderate in degree of protection and requires concentrations in the 10(-4) molar range. In contrast to ATA, both of these substances were inactive when tested for prevention of the binding of the OKT4A monoclonal antibody to the CD4 receptor and also for inhibition of HIV-1 reverse transcriptase. These substances therefore appear act by a mechanism that is distinct from that of polymeric ATA. Several active and inactive structural analogues of 3 and 5 were also synthesized. The anti-HIV activity in this series seems to depend on the presence of anionic carboxylate groups, since the methyl esters 4, 6, and 12 were uniformly inactive. The diphenylmethanes 8, 14, 18, and 19 also reproducibly inhibited the cytopathic effect of HIV-1 in CEM cell culture.

  DOI：

  10.1021/jm00105a053

文献信息

• CUSHMAN, MARK;KANAMATHAREDDY, SUSEELA;DE, CLERCQ ERIK;SCHOLS, DOMINIQUE;G+, J. MED. CHEM., 34,(1991) N, C. 337-342
  作者：CUSHMAN, MARK、KANAMATHAREDDY, SUSEELA、DE, CLERCQ ERIK、SCHOLS, DOMINIQUE、G+

  DOI：——

  日期：——
• [EN] NEW ANTI-HIV COMPOUNDS BELONGING TO AURINTRICARBOXYLIC ACID
  申请人：THE UNITED STATES OF AMERICA, represented by THE SECRETARY, UNITED STATES DEPARTMENT OF COMMERCE

  公开号：WO1991006589A1

  公开（公告）日：1991-05-16

  (EN) The invention relates to the synthesis of compounds with anti-retroviral activity. The synthesis of substantially pure aurintricarboxylic acid monomer and structurally defined polymers, analogs and derivatives thereof, is described. The compounds are shown to have potent anti-retroviral activity, particularly against HIV-1.(FR) Synthèse de composés présentant une activité antirétrovirale. La synthèse d'un monomère d'acide aurintricarboxylique pur ainsi que de polymères structurellement définis, d'analogues et de dérivés de ceux-ci, est décrite. On a démontré que les composés présentent une activité antirétrovirale puissante, notamment contre le VIH-1.
• Synthesis and anti-HIV activities of low molecular weight aurintricarboxylic acid fragments and related compounds
  作者：Mark Cushman、Suseela Kanamathareddy、Erik De Clercq、Dominique Schols、Mark E. Goldman、Julie A. Bowen

  DOI：10.1021/jm00105a053

  日期：1991.1

  Several compounds corresponding to fragments of the schematic representation of the polymeric structure of aurintricarboxylic acid (ATA) have been prepared and tested for prevention of the cytopathic effect of HIV-1 and HIV-2 in MT-4 cell culture and HIV-1 in CEM cell culture. Both the triphenylcarbinol 3 as well as the triphenylmethane 5 were found to afford protection against the cytopathogenicity of HIV-2 in MT-4 cells and HIV-1 in CEM cells, but they were inactive against HIV-1 in MT-4 cells. Both substances were also found to inhibit syncytium formation when MOLT-4 cells were cocultured with HIV-2-infected HUT-78 cells, but were inactive in this assay against HIV-1-infected cells. When observed, the activity is generally moderate in degree of protection and requires concentrations in the 10(-4) molar range. In contrast to ATA, both of these substances were inactive when tested for prevention of the binding of the OKT4A monoclonal antibody to the CD4 receptor and also for inhibition of HIV-1 reverse transcriptase. These substances therefore appear act by a mechanism that is distinct from that of polymeric ATA. Several active and inactive structural analogues of 3 and 5 were also synthesized. The anti-HIV activity in this series seems to depend on the presence of anionic carboxylate groups, since the methyl esters 4, 6, and 12 were uniformly inactive. The diphenylmethanes 8, 14, 18, and 19 also reproducibly inhibited the cytopathic effect of HIV-1 in CEM cell culture.