4-Thiodiacetylamino-benzolsulfonsaeureamid | 83089-02-5

• 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-Thiodiacetylamino-benzolsulfonsaeureamid
• 英文别名: 2-(2-oxo-2-(4-sulfamoylphenylamino)ethylthio)acetic acid；((4-Sulfamoyl-phenylcarbamoyl)-methylsulfanyl)-acetic acid；2-[2-oxo-2-(4-sulfamoylanilino)ethyl]sulfanylacetic acid
• CAS: 83089-02-5
• 化学式: C₁₀H₁₂N₂O₅S₂
• mdl: MFCD02668090
• 分子量: 304.348
• InChiKey: SUOPBYMZIWGWDM-UHFFFAOYSA-N

物化性质

• 熔点：
  181-182 °C
• 密度：
  1.576±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  160
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-Thiodiacetylamino-benzolsulfonsaeureamid 在 盐酸 、 水 、 N,N-二异丙基乙胺 、 三苯基膦 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.67h， 生成 (S)-3-(4-ethoxyphenyl)-2-(2-(2-oxo-2-(4-sulfamoylphenylamino)ethylthio)acetamido)propanoic acid
  参考文献：
  名称：

  Discovery of Small-Molecule Interleukin-2 Inhibitors from a DNA-Encoded Chemical Library

  摘要：

  AbstractLibraries of chemical compounds individually coupled to encoding DNA tags (DNA‐encoded chemical libraries) hold promise to facilitate exceptionally efficient ligand discovery. We constructed a high‐quality DNA‐encoded chemical library comprising 30 000 drug‐like compounds; this was screened in 170 different affinity capture experiments. High‐throughput sequencing allowed the evaluation of 120 million DNA codes for a systematic analysis of selection strategies and statistically robust identification of binding molecules. Selections performed against the tumor‐associated antigen carbonic anhydrase IX (CA IX) and the pro‐inflammatory cytokine interleukin‐2 (IL‐2) yielded potent inhibitors with exquisite target specificity. The binding mode of the revealed pharmacophore against IL‐2 was confirmed by molecular docking. Our findings suggest that DNA‐encoded chemical libraries allow the facile identification of drug‐like ligands principally to any protein of choice, including molecules capable of disrupting high‐affinity protein–protein interactions.

  DOI：

  10.1002/chem.201200952
• 作为产物：
  描述：

  硫代羟基乙酸酐 、 磺胺 生成 4-Thiodiacetylamino-benzolsulfonsaeureamid
  参考文献：
  名称：

  Notes-Sulfonamides and Some Related Materials

  摘要：

  DOI：

  10.1021/jo01068a600

文献信息

• Notes-Sulfonamides and Some Related Materials
  作者：H Morrill、George Steahly、Ferdinand Zienty

  DOI：10.1021/jo01068a600

  日期：1961.10
• EL-EZBAWY, SAMIA, R., FECS: 1 INT. CONF. CHEM. AND BIOTECHNOL. BIOLOGICALLY ACT. NATUR. PROD. V+
  作者：EL-EZBAWY, SAMIA, R.

  DOI：——

  日期：——
• Discovery of Small-Molecule Interleukin-2 Inhibitors from a DNA-Encoded Chemical Library
  作者：Markus Leimbacher、Yixin Zhang、Luca Mannocci、Michael Stravs、Tim Geppert、Jörg Scheuermann、Gisbert Schneider、Dario Neri

  DOI：10.1002/chem.201200952

  日期：2012.6.18

  AbstractLibraries of chemical compounds individually coupled to encoding DNA tags (DNA‐encoded chemical libraries) hold promise to facilitate exceptionally efficient ligand discovery. We constructed a high‐quality DNA‐encoded chemical library comprising 30 000 drug‐like compounds; this was screened in 170 different affinity capture experiments. High‐throughput sequencing allowed the evaluation of 120 million DNA codes for a systematic analysis of selection strategies and statistically robust identification of binding molecules. Selections performed against the tumor‐associated antigen carbonic anhydrase IX (CA IX) and the pro‐inflammatory cytokine interleukin‐2 (IL‐2) yielded potent inhibitors with exquisite target specificity. The binding mode of the revealed pharmacophore against IL‐2 was confirmed by molecular docking. Our findings suggest that DNA‐encoded chemical libraries allow the facile identification of drug‐like ligands principally to any protein of choice, including molecules capable of disrupting high‐affinity protein–protein interactions.