4-[(4-氨基苯基)二氮烯基]苯磺酰胺 | 59553-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 中文名称: 4-[(4-氨基苯基)二氮烯基]苯磺酰胺
• 英文名称: 4-[(4-sulfonamidophenyl)azo]aniline
• 英文别名: Sulfonamid III；4-Amino-4'-sulfamoyl-azobenzol；4-Amino-azobenzolsulfonsaeure-(4')-amid；4-(4-amino-phenylazo)-benzenesulfonic acid amide；4-(4-Amino-phenylazo)-benzolsulfonsaeure-amid；4-((4-Aminophenyl)diazenyl)benzenesulfonamide；4-[(4-aminophenyl)diazenyl]benzenesulfonamide
• CAS: 59553-77-4
• 化学式: C₁₂H₁₂N₄O₂S
• 分子量: 276.319
• InChiKey: JSHXITVMUADQEA-UHFFFAOYSA-N

物化性质

• 熔点：
  234-236 °C
• 沸点：
  532.7±56.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-[(4-氨基苯基)二氮烯基]苯磺酰胺 在 丙酮 作用下， 生成 4-Acetamino-4'-sulfamoyl-azobenzol
  参考文献：
  名称：

  Madeja, Societatis Scientiarum Lodziensis, Acta Chimica, 1955, vol. 1, p. 53,68

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium (4-((4-sulfamoylphenyl)diazenyl)phenylamino)methanesulfonate 在 sodium hydroxide 作用下， 以 水 为溶剂， 以62%的产率得到4-[(4-氨基苯基)二氮烯基]苯磺酰胺
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Diazenylbenzenesulfonamides are potent and selective inhibitors of the tumor-associated isozymes IX and XII over the cytosolic isoforms I and II

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.09.003

文献信息

• Rapid and direct spectrophotometric method for kinetics studies and routine assay of peroxidase based on aniline diazo substrates
  作者：Fatemeh Mirazizi、Azita Bahrami、Kamahldin Haghbeen、Hossein Shahbani Zahiri、Mehdi Bakavoli、Raymond L. Legge

  DOI：10.3109/14756366.2015.1103234

  日期：2016.11.1

  Current spectrophotometrically based peroxidase assay methods are based on the production of chromophoric substances at the end of the enzymatic reaction. The ambiguity regarding the formation and identity of the final chromophoric product and its possible reactions with other molecules have raised concerns about the accuracy of these methods. This can be of serious concern in inhibition studies. A novel

  过氧化物酶是在生物体中起重要作用的普遍存在的酶。当前基于分光光度法的过氧化物酶测定方法是基于在酶促反应结束时发色物质的产生。关于最终发色产物的形成和身份以及其与其他分子可能的反应的模棱两可，引起了人们对这些方法的准确性的担忧。这在抑制研究中可能会引起严重关注。介绍了一种基于直接测量可溶性苯胺重氮底物的过氧化物酶分光光度法。除常规分析外，该方法还可用于全面的动力学研究。引入4-[（4-磺基苯基）偶氮]苯胺（λmax= 390 nm，ɛ= 32 880 M（-1）cm（-1）在pH 4.5至9下）用于过氧化物酶的常规分析。该化合物可商购，并被标记为食用染料。使用该方法，过氧化物酶的检出限为0.05 nmol mL（-1）。
• 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.
• Madeja, Societatis Scientiarum Lodziensis, Acta Chimica, 1955, vol. 1, p. 53,68
  作者：Madeja

  DOI：——

  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.