(E)-4-(4-hydroxyphenyldiazenyl)benzenesulfonamide | 62143-36-6

• 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: (E)-4-(4-hydroxyphenyldiazenyl)benzenesulfonamide
• 英文别名: 4-[(4-sulfonamidophenyl)azo]phenol
• CAS: 62143-36-6
• 化学式: C₁₂H₁₁N₃O₃S
• 分子量: 277.304
• InChiKey: IPPFWRRJWLCWGK-CCEZHUSRSA-N

物化性质

• 沸点：
  545.1±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  19.0
• 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：
  105.11
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (E)-4-(4-hydroxyphenyldiazenyl)benzenesulfonamide 以94%的产率得到4-[(E)-(4-methoxyphenyl)diazenyl]benzenesulfonamide
  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：

  磺胺 、 苯酚 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 甲醇 为溶剂， 以43%的产率得到(E)-4-(4-hydroxyphenyldiazenyl)benzenesulfonamide
  参考文献：
  名称：

  Azobenzene-based inhibitors of human carbonic anhydrase II

  摘要：

  芳基磺胺是一类广泛使用的药物，用于抑制碳酸酐酶。在我们的光致变色药物基团项目中，我们对含有偶氮苯基磺胺的化合物进行了探索，以阻断人类碳酸酐酶II（hCAII）的催化活性。在这里，我们报告了对九种光致变色磺胺化合物进行合成和体外评价，以用于hCAII。所有分子均为偶氮苯-4-磺胺，其在4´-位置被不同的功能基团取代，并通过X射线晶体学进行表征。我们旨在研究电子给体或电子吸引基团对抑制常数Ki的影响。通过结合合成的偶氮苯之一与hCAII晶体结构结合的结构，我们发现电子结构并不强烈影响抑制作用。总的来说，所有化合物都是hCAII的强效阻断剂，Ki = 25-65 nM，可能是光致变色的，因此结合了化学合成、晶体学和酶动力学研究。

  DOI：

  10.3762/bjoc.11.127

文献信息

• Facile Synthesis of Catechol Azo Dyes
  作者：Kamaldin Haghbeen、Eng Wui Tan

  DOI：10.1021/jo972151z

  日期：1998.6.1
• Azobenzene-based inhibitors of human carbonic anhydrase II
  作者：Leander Simon Runtsch、David Michael Barber、Peter Mayer、Michael Groll、Dirk Trauner、Johannes Broichhagen

  DOI：10.3762/bjoc.11.127

  日期：——

  Aryl sulfonamides are a widely used drug class for the inhibition of carbonic anhydrases. In the context of our program of photochromic pharmacophores we were interested in the exploration of azobenzene-containing sulfonamides to block the catalytic activity of human carbonic anhydrase II (hCAII). Herein, we report the synthesis and in vitro evaluation of a small library of nine photochromic sulfonamides towards hCAII. All molecules are azobenzene-4-sulfonamides, which are substituted by different functional groups in the 4´-position and were characterized by X-ray crystallography. We aimed to investigate the influence of electron-donating or electron-withdrawing substituents on the inhibitory constant K_i. With the aid of an hCAII crystal structure bound to one of the synthesized azobenzenes, we found that the electronic structure does not strongly affect inhibition. Taken together, all compounds are strong blockers of hCAII with K_i = 25–65 nM that are potentially photochromic and thus combine studies from chemical synthesis, crystallography and enzyme kinetics.

  芳基磺胺是一类广泛使用的药物，用于抑制碳酸酐酶。在我们的光致变色药物基团项目中，我们对含有偶氮苯基磺胺的化合物进行了探索，以阻断人类碳酸酐酶II（hCAII）的催化活性。在这里，我们报告了对九种光致变色磺胺化合物进行合成和体外评价，以用于hCAII。所有分子均为偶氮苯-4-磺胺，其在4´-位置被不同的功能基团取代，并通过X射线晶体学进行表征。我们旨在研究电子给体或电子吸引基团对抑制常数Ki的影响。通过结合合成的偶氮苯之一与hCAII晶体结构结合的结构，我们发现电子结构并不强烈影响抑制作用。总的来说，所有化合物都是hCAII的强效阻断剂，Ki = 25-65 nM，可能是光致变色的，因此结合了化学合成、晶体学和酶动力学研究。
• 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.