4-(4'-hydroxyphenyl)diazenylbenzenesulfonamide | 2497-37-2

• 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'-hydroxyphenyl)diazenylbenzenesulfonamide
• 英文别名: 4-(4-hydroxy-phenylazo)-benzenesulfonic acid amide；4-(4-Hydroxy-phenylazo)-benzolsulfonsaeure-amid；4'-Hydroxy-azobenzol-sulfonsaeure-(4)-amid；p-Hydroxy-azobenzolsulfonamid；4-[(4-hydroxyphenyl)diazenyl]benzenesulfonamide
• CAS: 2497-37-2
• 化学式: C₁₂H₁₁N₃O₃S
• 分子量: 277.304
• InChiKey: IPPFWRRJWLCWGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4'-hydroxyphenyl)diazenylbenzenesulfonamide 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 C₁₅H₁₃N₃O₄S
  参考文献：
  名称：

  用于酶活性光化学调节的非共价光开关

  摘要：

  基于聚合物抑制剂封装方法合成了一种用于调节酶活性的非共价光开关。该方法将偶氮苯修饰的抑制剂非共价地锚定到封装酶的活性位点，从而允许使用光对酶活性进行可逆控制。这种方法提供了一种有前途的策略来调节酶的活性，而无需基因突变或酶的化学修饰。

  DOI：

  10.1002/anie.202116073
• 作为产物：
  描述：

  磺胺 、 苯酚 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.67h， 以80%的产率得到4-(4'-hydroxyphenyl)diazenylbenzenesulfonamide
  参考文献：
  名称：

  用于酶活性光化学调节的非共价光开关

  摘要：

  基于聚合物抑制剂封装方法合成了一种用于调节酶活性的非共价光开关。该方法将偶氮苯修饰的抑制剂非共价地锚定到封装酶的活性位点，从而允许使用光对酶活性进行可逆控制。这种方法提供了一种有前途的策略来调节酶的活性，而无需基因突变或酶的化学修饰。

  DOI：

  10.1002/anie.202116073

文献信息

• Design, Synthesis and Biological Evaluation of 1,4-Benzenesulfonamide Derivatives as Glyoxalase I Inhibitors
  作者：Suaad Abdallah Audat、Qosay Ali Al-Balas、Buthina Abdallah Al-Oudat、Mo'ad Jamil Athamneh、Amanda Bryant-Friedrich

  DOI：10.2147/dddt.s356621

  日期：——

  azo coupling reaction of aniline derivatives and activated substituted aromatic compounds. To understand the binding mode of the active compounds at the active site of Glx-I, docking studies were performed. Results: Structure activity relationship (SAR) studies were accomplished which led to the identification of several compounds that showed potent inhibitory activity with IC50 values below 10 μM. Among

  背景：乙二醛酶系统是防御细胞机制之一，通过将细胞毒性甲基乙二醛转化为无毒乳酸，保护细胞免受内源性有害代谢物（主要是甲基乙二醛（MG））的侵害。乙二醛酶系统由两种酶乙二醛酶I、乙二醛酶II和催化量的还原型谷胱甘肽组成。癌细胞过度表达乙二醛酶 I，使其成为癌症治疗的靶点。已经进行了许多研究来鉴定有效的 Glx-I 抑制剂。 方法：为了发现和开发新型Glx-I抑制剂，设计、合成了一系列1,4-苯磺酰胺衍生物，并针对人Glx-I酶进行了体外生物学评价。根据搜索美国国家癌症研究所 (NCI) 数据库获得的热门化合物，设计了 17 种化合物。利用苯胺衍生物和活化的取代芳香族化合物的偶氮偶联反应完成了目标化合物( 13-29 )的合成。为了了解活性化合物在 Glx-I 活性位点的结合模式，进行了对接研究。 结果：完成了结构活性关系 (SAR) 研究，鉴定出几种显示出有效抑制活性且 IC 50值低于 10
• Darstellung aromatischer Azidoverbindungen nach der Dutt-Wormallschen Reaktion
  作者：H. Bretschneider、H. Rager

  DOI：10.1007/bf00899340

  日期：——
• Carbonic anhydrase inhibitors. Diazenylbenzenesulfonamides are potent and selective inhibitors of the tumor-associated isozymes IX and XII over the cytosolic isoforms I and II
  作者：Fabrizio Carta、Alfonso Maresca、Andrea Scozzafava、Daniela Vullo、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2009.09.003

  日期：2009.10

  A series of diazenylbenzenesulfonamides, azo-dye derivatives of sulfanilamide or metanilamide incorporating phenol and amine moieties, were tested for inhibition of the tumor-associated isozymes of carbonic anhydrase (CA, EC 4.2.1.1), CA IX and XII. These compounds showed moderate-low inhibitory activities against the cytosolic isoforms CA I and II (offtargets) and excellent, low nanomolar inhibitory activity against the transmembrane CA IX and XII (K(I)s in the range of 3.5-63 nM against CA IX and 5.0-69.4 nM against CA XII, respectively). The selectivity ratio for inhibiting the tumor-associated CA IX over the offtarget CA II was in the range of 15-104 for these diazenylbenzenesulfonamides, making them among the most isoform-selective inhibitors targeting tumor-associated CAs (over the ubiquitous CA II). Since CA IX/XII were recently shown to be both therapeutic and diagnostic targets for hypoxic solid tumors overexpressing these proteins, such compounds held promise for the management of hypoxic tumors, which are largely non-responsible to classical chemo-and radio-therapy. (C) 2009 Elsevier Ltd. All rights reserved.
• Carbonic anhydrase inhibitors. Inhibition of the Rv1284 and Rv3273 β-carbonic anhydrases from Mycobacterium tuberculosis with diazenylbenzenesulfonamides
  作者：Alfonso Maresca、Fabrizio Carta、Daniela Vullo、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2009.07.088

  日期：2009.9

  A series of diazenylbenzenesulfonamides obtained from sulfanilamide or metanilamide by diazotization followed by coupling with phenols or amines, was tested for the inhibition of the beta-carbonic anhydrases (CAs, EC 4.2.1.1) encoded by the genes Rv1284 and Rv3273 of Mycobacterium tuberculosis. Several low micromolar inhibitors of the two enzymes were detected, with prontosil being the best inhibitor (K(I)s of 126-148 nM). Inhibition of pathogenic beta-CAs may lead to the development of antiinfectives with a new mechanism of action, devoid of resistance problems encountered with classical antibiotics. (C) 2009 Elsevier Ltd. All rights reserved.
• Monche, Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, 1952, vol. 48, p. 499,511
  作者：Monche

  DOI：——

  日期：——