4-(4-二甲基氨基苯基)偶氮苯磺酰胺 | 2435-64-5

• 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-(4-二甲基氨基苯基)偶氮苯磺酰胺
• 英文名称: dabsyl amide
• 英文别名: 4-(4-dimethylamino-phenylazo)-benzenesulfonic acid amide；4-(4-Dimethylamino-phenylazo)-benzolsulfonsaeure-amid；4'-Dimethylamino-azobenzol-sulfonsaeure-(4)-amid；4-(4-Dimethylamino-benzolazo)-benzolsulfonsaeureamid；Benzenesulfonamide, p-((p-(dimethylamino)phenyl)azo)-；4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonamide
• CAS: 2435-64-5
• 化学式: C₁₄H₁₆N₄O₂S
• 分子量: 304.373
• InChiKey: NZUPTIDAKYYKGC-UHFFFAOYSA-N

物化性质

• 密度：
  1.2638 (rough estimate)
• 溶解度：
  0.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  4-(4-二甲基氨基苯基)偶氮苯磺酰胺 在 sodium hypochlorite 、 水 作用下， 生成 4-(4-dimethylamino-phenylazo)-benzenesulfonic acid chloroamide; sodium-salt
  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：

  4-二甲胺基苯基偶氮苯磺酰氯 在 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到4-(4-二甲基氨基苯基)偶氮苯磺酰胺
  参考文献：
  名称：

  铑催化的[2 + 2 + 2]环加成反应合成非蛋白质的苯丙氨酸衍生物†

  摘要：

  通过Rh（I）催化的对映纯和具有不同保护基团的外消旋炔丙基甘氨酸氨基酸和二炔之间的Rh（I）催化的[2 + 2 + 2]环加成反应，可以有效地制备非蛋白质苯基丙氨酸衍生物。通过选择最合适的二炔反应伙伴，将包括标签如丹磺酰基或达布磺酰基在内的各种取代基引入到氨基酸衍生物的芳环上。

  DOI：

  10.1039/b910961g

文献信息

• A Chemosensor Bearing Sulfonyl Azide Moieties for Selective Chromo-Fluorogenic Hydrogen Sulfide Recognition in Aqueous Media and in Living Cells
  作者：Luis E. Santos-Figueroa、Cristina de laTorre、Sameh El Sayed、Félix Sancenón、Ramón Martínez-Máñez、Ana M. Costero、Salvador Gil、Margarita Parra

  DOI：10.1002/ejoc.201301514

  日期：2014.3

  A simple chemodosimeter based on a sulfonyl azide dye (1-Az), which displayed a highly selective response toward hydrogen sulfide anion in mixed aqueous media, was synthesised and characterised. Addition of hydrogen sulfide to acetonitrile/HEPES 1:1 solutions of 1-Az induced a clear colour change from red-orange to yellow, which was easily detected by the naked eye, and by an enhancement in the emission

  合成并表征了一种基于磺酰叠氮化物染料 (1-Az) 的简单化学剂量计，该染料对混合水性介质中的硫化氢阴离子显示出高度选择性响应。将硫化氢添加到 1-Az 的乙腈/HEPES 1:1 溶液中会引起明显的颜色变化，从红橙色变为黄色，这很容易被肉眼检测到，并且发射强度会增强。其他常见的阴离子、含硫醇的生物分子和氧化剂不会在探针中引起任何明显的颜色或荧光调制。化学剂量计还显示出良好的灵敏度，使用 UV/Vis 或荧光测量的检测限分别为 11.91 和 0.63 μM。此外，1-Az 可用于微摩尔浓度的细胞内 HS 的实时荧光成像。
• High performance liquid chromatographic determination of naturally occurring primary and secondary amines with dabsyl chloride
  作者：Jen-Kun. Lin、Chen-Ching. Lai

  DOI：10.1021/ac50054a008

  日期：1980.4.1
• 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.
• van Lente; Pope, 1946, vol. 39, p. 77
  作者：van Lente、Pope

  DOI：——

  日期：——