5-[双(3-羧基-4-羟基苯基)-羟甲基]-2-羟基苯甲酸 | 639-56-5

• 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)-羟甲基]-2-羟基苯甲酸
• 英文名称: 3,3',3''-tricarboxy-4,4',4''-trihydroxytriphenylcarbinol
• 英文别名: trisalicylcarbinol；Tris(3-Carboxy-4-hydroxyphenyl)carbinol；5-[bis(3-carboxy-4-hydroxyphenyl)-hydroxymethyl]-2-hydroxybenzoic acid
• CAS: 639-56-5
• 化学式: C₂₂H₁₆O₁₀
• 分子量: 440.363
• InChiKey: HLOZTRLQBMUCQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  804.6±65.0 °C(Predicted)
• 密度：
  1.673±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 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：
  193
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3,3'-dicarboxy-5,5'-dichloro-4,4'-dihydroxydiphenylmethane 在 palladium on activated charcoal 760 torr 、 硫酸 、 氢气 、 sodium nitrite 作用下， 以 乙醇 、 三乙胺 为溶剂， 反应 66.0h， 生成 5-[双(3-羧基-4-羟基苯基)-羟甲基]-2-羟基苯甲酸
  参考文献：
  名称：

  误认为金三羧酸（ATA）结构的共价水合物的合成

  摘要：

  已经合成了三苯基甲醇6，它是公认的但不正确的金三羧酸（ATA）结构的共价水合物，并已发现在CEM-V淋巴细胞培养中可抵抗HIV-1的细胞病变作用。该合成涉及纯亚甲基二水杨酸的首次制备（5）。除了（聚合）ATA以外，三苯基甲醇6还为开发潜在的抗艾滋病药物提供了新的线索。即使在7天后，在室温下在存在过量的18氧标记水的情况下，中心碳氧6仍未交换，这表明6和1之间没有平衡。 在这些条件下。

  DOI：

  10.1016/s0040-4020(01)81957-8

文献信息

• Selective inhibition of the membrane attack complex of complement by low molecular weight components of the aurin tricarboxylic acid synthetic complex
  申请人：McGeer Patrick L.

  公开号：US20130035388A1

  公开（公告）日：2013-02-07

  This patent pertains to selective inhibition of assembly of the membrane attack complex of complement by use of less than 1 kDa molecular weight forms of the aurin tricarboxylic acid synthetic complex (ATAC), and their derivatives. It further pertains to the use of these materials to treat human conditions where there is evidence of self destruction of host tissue by the membrane attack complex. These diseases include, but are not limited to, Alzheimer disease, age related macular degeneration, and atherosclerosis.

  这项专利涉及使用小于1 kDa分子量的aurin三羧酸合成复合物（ATAC）及其衍生物，有选择性地抑制补体膜攻击复合物的组装。它还涉及使用这些材料来治疗人类疾病，其中存在宿主组织自我破坏的证据，这些疾病包括但不限于阿尔茨海默病，年龄相关性黄斑变性和动脉粥样硬化。
• Selective inhibition of the membrane attack complex of complement by low molecular weight components of the aurin tricarboxylic synthetic complex
  申请人：McGeer Patrick L.

  公开号：US10966945B2

  公开（公告）日：2021-04-06

  This patent pertains to selective inhibition of assembly of the membrane attack complex of complement by use of less than 1 kDa molecular weight forms of the aurin tricarboxylic acid synthetic complex (ATAC), and their derivatives. It further pertains to the use of these materials to treat human conditions where there is evidence of self destruction of host tissue by the membrane attack complex. These diseases include, but are not limited to, Alzheimer disease, age related macular degeneration, and atherosclerosis.

  本专利涉及通过使用分子量小于 1 kDa 的三羧酸曙红合成复合物 (ATAC) 及其衍生物，选择性地抑制补体膜攻击复合物的组装。它还涉及使用这些材料治疗有证据表明膜攻击复合物对宿主组织造成自我破坏的人类疾病。这些疾病包括但不限于阿尔茨海默病、老年性黄斑变性和动脉粥样硬化。
• 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.