4-[(4-{[(4-carboxy-2-hydroxyphenyl)amino]methyl}benzyl)amino]-3-hydroxybenzoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[(4-{[(4-carboxy-2-hydroxyphenyl)amino]methyl}benzyl)amino]-3-hydroxybenzoic acid
• 英文别名: 4-[[4-[(4-Carboxy-2-hydroxyanilino)methyl]phenyl]methylamino]-3-hydroxybenzoic acid
• 化学式: C₂₂H₂₀N₂O₆
• 分子量: 408.411
• InChiKey: APNFNKGFYOGLPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  139
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-氨基-3-羟基苯甲酸甲酯 在 甲醇 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.75h， 生成 4-[(4-{[(4-carboxy-2-hydroxyphenyl)amino]methyl}benzyl)amino]-3-hydroxybenzoic acid
  参考文献：
  名称：

  Synthesis of Analogues of Congo Red and Evaluation of Their Anti-Prion Activity

  摘要：

  No cure as of yet exists for any of the transmissible spongiform encephalopathies. In this paper, we describe the synthesis of analogues of Congo red and evaluation against a cellular model of infection, the SMB (scrapie mouse brain) persistently infected cell line, for their ability to inhibit the infectivity of the abnormal form of prion protein (PrP-res). The compounds have also been tested for their ability to inhibit the polymerization of PrPC by PrP-res. A number of analogues showed inhibition of PrP-res infectivity at nanomolar concentrations. Several analogues show promise; the most active compound, 2a, inhibits the formation of PrP-res in SMB cells with an EC50 of 25-50 nM.

  DOI：

  10.1021/jm049922t

文献信息

• [EN] ANALOGUES OF CONGO RED AND EVALUATION OF THEIR ANTI-PRION ACTIVITY<br/>[FR] COMPOSES
  申请人：MEDICAL RES COUNCIL

  公开号：WO2005085189A3

  公开（公告）日：2005-12-29
• [EN] COMPOUNDS<br/>[FR] COMPOSES
  申请人：MEDICAL RES COUNCIL

  公开号：WO2005085189A2

  公开（公告）日：2005-09-15

  The present invention relates to compounds of formula (I), or pharmaceutically acceptable salts thereof, wherein X is selected from (II) and (III), Y is selected from SO2NH, CONH, CH=N, CH2NH and CH=CH; R1-5 are each independently selected from H, OH, OR6, CO2H, C02R7, NO2, CN CONR8R9, CONHR10, CO2(CH2)nCO2R11, CO2(CH2)mO(CO)R12, CO2CHR13COR14, CONH(CH2)pCO2R15, CONH(CH2)qO(CO)R16, CONHCHRI7COR18; R6-18 are each independently hydrocarbyl; n, m, p and q are each independently 1, 2, 3 or 4; with the proviso that when X is phenyl, Y is CH=CH, R3 is OH and R1, R4 and R5 are H, R2 is other than COON. Further aspects of the invention relate to the use of such compounds in the preparation of a medicament for the treatment or prevention of transmissible spongiform encephalopathies (TSEs), and pharmaceutical compositions comprising the same.
• Synthesis of Analogues of Congo Red and Evaluation of Their Anti-Prion Activity
  作者：Shane Sellarajah、Tamuna Lekishvili、Claire Bowring、Andrew R. Thompsett、Helene Rudyk、Christopher R. Birkett、David R. Brown、Ian H. Gilbert

  DOI：10.1021/jm049922t

  日期：2004.10.1

  No cure as of yet exists for any of the transmissible spongiform encephalopathies. In this paper, we describe the synthesis of analogues of Congo red and evaluation against a cellular model of infection, the SMB (scrapie mouse brain) persistently infected cell line, for their ability to inhibit the infectivity of the abnormal form of prion protein (PrP-res). The compounds have also been tested for their ability to inhibit the polymerization of PrPC by PrP-res. A number of analogues showed inhibition of PrP-res infectivity at nanomolar concentrations. Several analogues show promise; the most active compound, 2a, inhibits the formation of PrP-res in SMB cells with an EC50 of 25-50 nM.