4-(3,4-dihydroxy-phenylazo)-benzenesulfonic acid amide | 99989-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-(3,4-dihydroxy-phenylazo)-benzenesulfonic acid amide
• 英文别名: 4-(3,4-Dihydroxy-phenylazo)-benzolsulfonsaeure-amid；3'.4'-Dihydroxy-azobenzol-sulfonsaeure-(4)-amid
• CAS: 99989-56-7
• 化学式: C₁₂H₁₁N₃O₄S
• 分子量: 293.303
• InChiKey: OVFNJGSXFVWDJP-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  125.34
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-异丙基苯异氰酸酯 、 4-(3,4-dihydroxy-phenylazo)-benzenesulfonic acid amide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Selective COX-2 inhibitors. Part 1: Synthesis and biological evaluation of phenylazobenzenesulfonamides

  摘要：

  A series of phenylazobenzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclo-oxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB) and an enzymatic assay using purified ovine enzymes. Extensive structure activity relationships (SAR) were studied within this series, and several of selective COX-2 inhibitors have been identified. Among them, compound 8, 4-(4-amino-2-methylsulfanyl-phenylazo)benzenesulfonamide, showed a potent inhibitory activity to the cyclooxygenase enzymes (IC50's for COX-1: 23.28 mu M; COX-2: 2.04 mu M), being active but less COX-2 selective than celecoxib. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.036
• 作为产物：
  描述：

  木榴油 在 吡啶 、 盐酸 、 三氯化铝 、 potassium carbonate 、 sodium nitrite 作用下， 以 氯仿 为溶剂， 反应 31.33h， 生成 4-(3,4-dihydroxy-phenylazo)-benzenesulfonic acid amide
  参考文献：
  名称：

  Facile Synthesis of Catechol Azo Dyes

  摘要：

  DOI：

  10.1021/jo972151z

文献信息

• Barton; Linnell; Senior, Quarterly Journal of Pharmacy and Pharmacology, 1945, vol. 18, p. 41,43
  作者：Barton、Linnell、Senior

  DOI：——

  日期：——
• Selective COX-2 inhibitors. Part 1: Synthesis and biological evaluation of phenylazobenzenesulfonamides
  作者：Wei-Jern Tsai、Young-Ji Shiao、Shwu-Jiuan Lin、Wen-Fei Chiou、Lie-Chwen Lin、Tsang-Hsiung Yang、Che-Ming Teng、Tain-Shung Wu、Li-Ming Yang

  DOI：10.1016/j.bmcl.2006.06.036

  日期：2006.9

  A series of phenylazobenzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclo-oxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB) and an enzymatic assay using purified ovine enzymes. Extensive structure activity relationships (SAR) were studied within this series, and several of selective COX-2 inhibitors have been identified. Among them, compound 8, 4-(4-amino-2-methylsulfanyl-phenylazo)benzenesulfonamide, showed a potent inhibitory activity to the cyclooxygenase enzymes (IC50's for COX-1: 23.28 mu M; COX-2: 2.04 mu M), being active but less COX-2 selective than celecoxib. (c) 2006 Elsevier Ltd. All rights reserved.
• Facile Synthesis of Catechol Azo Dyes
  作者：Kamaldin Haghbeen、Eng Wui Tan

  DOI：10.1021/jo972151z

  日期：1998.6.1