5-[(3-羧基-4-羟基-5-甲基苯基)甲基]-2-羟基-3-甲基苯甲酸 | 2581-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-[(3-羧基-4-羟基-5-甲基苯基)甲基]-2-羟基-3-甲基苯甲酸
• 英文名称: 5,5’-methylenedi-2,3-cresotic acid
• 英文别名: 5,5'-Methylenedi-2,3-cresotic acid；5-[(3-carboxy-4-hydroxy-5-methylphenyl)methyl]-2-hydroxy-3-methylbenzoic acid
• CAS: 2581-36-4
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: UPLNCYRSCVJILM-UHFFFAOYSA-N

物化性质

• 熔点：
  268 °C (decomp)
• 沸点：
  560.4±50.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[(3-羧基-4-羟基-5-甲基苯基)甲基]-2-羟基-3-甲基苯甲酸 生成 3-(3-carboxy-4-hydroxy-5-methyl-benzylidene)-5-methyl-6-oxo-cyclohexa-1,4-dienecarboxylic acid
  参考文献：
  名称：

  DE231992

  摘要：

  公开号：
• 作为产物：
  描述：

  2-羟基-3-甲基苯甲酸甲酯 在 sodium hydroxide 、 硫酸 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-[(3-羧基-4-羟基-5-甲基苯基)甲基]-2-羟基-3-甲基苯甲酸
  参考文献：
  名称：

  Methylenedisalicylic acid derivatives: New PTP1B inhibitors that confer resistance to diet-induced obesity

  摘要：

  Methylenedisalicylic acid derivatives were synthesized and their inhibitory activities against protein tyrosine phosphalases (PTPases) examined. Two of the compounds, 8 and 9, showed K-i values of 9.4 and 6.3 mu M against PTP I B, 4- and 7-fold lower values compared to those against TC-PTP. They were reversible and slow-binding inhibitors against PTP I B. When compound 8 was fed to a mouse model, the weight gain and adipocyte fat storage induced by a high-fat-diet were significantly suppressed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.069

文献信息

• The Biological Effects of Structural Variation at the Meta Position of the Aromatic Rings and at the End of the Alkenyl Chain in the Alkenyldiarylmethane Series of Non-Nucleoside Reverse Transcriptase Inhibitors
  作者：Guozhang Xu、Mark Micklatcher、Maximilian A. Silvestri、Tracy L. Hartman、Jennifer Burrier、Mark C. Osterling、Heather Wargo、Jim A. Turpin、Robert W. Buckheit,、Mark Cushman

  DOI：10.1021/jm010212m

  日期：2001.11.1

  In an effort to elucidate a set of structure-activity relationships in the alkenyldiarylmethane (ADAM) series of non-nucleoside reverse transcriptase inhibitors, a number of modifications were made at two locations: (1) the meta positions of the two aromatic rings and (2) the end of the alkenyl chain. Forty-two new ADAMs were synthesized and evaluated for inhibition of the cytopathic effect of HIV-1(RF)

  为了阐明在烯基二芳基甲烷（ADAM）系列非核苷类逆转录酶抑制剂中的一系列结构活性关系，在两个位置进行了许多修饰：（1）两个芳环的间位和（ 2）烯基链的末端。合成了42种新的ADAM，并评估了它们在CEM-SS细胞培养中对HIV-1（RF）的细胞病变作用的抑制作用以及对HIV-1逆转录酶的抑制作用。发现芳族取代基的大小会影响抗HIV活性，Cl，CH（3）和Br取代基具有最佳活性，而较小（H和F）或较大（I和CF（3）则具有减弱的活性。 ））取代基。还发现烯基链末端的取代基会影响抗病毒活性，具有与甲基或乙基酯基团相关的最大活性，并且由于被高级酯，酰胺，硫化物，亚砜，砜，砜，酯，缩醛，酮，氨基甲酸酯，脲和硫脲取代而导致的活性降低。十二个新的ADAM显示出亚微摩尔EC（50）值，可抑制CEM-SS细胞中HIV-1（RF）的细胞病变作用。将选定的ADAM 19和21与先前发布的ADAM 15和17的
• Kahl, Chemische Berichte, 1898, vol. 31, p. 146
  作者：Kahl

  DOI：——

  日期：——
• 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.
• DE49970
  申请人：——

  公开号：——

  公开（公告）日：——
• DE223337
  申请人：——

  公开号：——

  公开（公告）日：——