4-[(4-methoxy-3-hydroxyphenyl)azo]benzenesulfonamide

• 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-[(4-methoxy-3-hydroxyphenyl)azo]benzenesulfonamide
• 化学式: C₁₃H₁₃N₃O₄S
• 分子量: 307.33
• InChiKey: AIRNGFONAMWZBC-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  114.34
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  甲苯-4-磺酸,2-羟基苯基酯 在 盐酸 、 氢氧化钾 、 sodium hydroxide 、 四丁基溴化铵 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 26.5h， 生成 4-[(4-methoxy-3-hydroxyphenyl)azo]benzenesulfonamide
  参考文献：
  名称：

  A colormetric assay for catechol-O-methyltransferase

  摘要：

  A series of catechol diazo dyes were synthesized and tested as substrates for the enzyme catechol-O-methyltransferase (COMT) with the aim of developing a sensitive HPLC assay method using visible wavelength light detection. A method was developed which allowed for the determination of the two regioisomeric methylated products of the COMT catalyzed reaction of 4-[(3,4-dihydroxyphenyl)azo]benzenesulfonate with S-adenosylmethionine (AdoMet). Separation of the assay components was achieved by reverse phase chromatography using an isocratic mobile phase. No pre-preparation of the assay samples was required. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.038

文献信息

• 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.
• A colormetric assay for catechol-O-methyltransferase
  作者：Karl Bailey、Rebecca Cowling、Eng Wui Tan、Daniel Webb

  DOI：10.1016/j.bmc.2003.10.038

  日期：2004.2

  A series of catechol diazo dyes were synthesized and tested as substrates for the enzyme catechol-O-methyltransferase (COMT) with the aim of developing a sensitive HPLC assay method using visible wavelength light detection. A method was developed which allowed for the determination of the two regioisomeric methylated products of the COMT catalyzed reaction of 4-[(3,4-dihydroxyphenyl)azo]benzenesulfonate with S-adenosylmethionine (AdoMet). Separation of the assay components was achieved by reverse phase chromatography using an isocratic mobile phase. No pre-preparation of the assay samples was required. (C) 2003 Elsevier Ltd. All rights reserved.