4-amino-N-(4-bromophenyl)benzenesulfonamide | 19837-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-N-(4-bromophenyl)benzenesulfonamide
• 英文别名: Sulfanilsaeure-(4-brom-anilid)；N¹-(p-Brom-phenyl)-sulfanilamid；sulfanilic acid-(4-bromo-anilide)
• CAS: 19837-76-4
• 化学式: C₁₂H₁₁BrN₂O₂S
• mdl: MFCD01016098
• 分子量: 327.202
• InChiKey: OSXZLZYALOCUSG-UHFFFAOYSA-N

物化性质

• 熔点：
  207-207.5 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  483.6±55.0 °C(Predicted)
• 密度：
  1.660±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 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：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二氯-1,4-萘醌 、 4-amino-N-(4-bromophenyl)benzenesulfonamide 以 乙醇 为溶剂， 反应 72.0h， 以59%的产率得到N-(4-bromophenyl)-4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide
  参考文献：
  名称：

  新型萘醌4-氨基苯磺酰胺/羧酰胺衍生物作为蛋白酶体抑制剂的设计，合成及生物学评价

  摘要：

  设计，合成和评估了一系列带有萘醌药效团的新颖的4-氨基苯磺酰胺/羧酰胺衍生物，它们对人乳腺癌细胞系（MCF-7）的蛋白酶体抑制和抗增殖活性。通过光谱和元素分析证实了合成化合物的结构。使用基于细胞的测定法进行蛋白酶体抑制活性的研究。抗蛋白酶体活性结果表明，大多数化合物对半胱天冬酶样（CL，β1亚基），胰蛋白酶样（TL，β2亚基）和胰凝乳蛋白酶样（ChT-L，β5亚基）活性具有不同百分比的抑制活性。蛋白酶体。在测试的化合物中，化合物14在磺酰胺基团的氮原子上带有5-氯-2-吡啶基环的化合物是该系列中活性最高的化合物，显示出更高的抑制作用，对ChT-L的IC 50值为9.90±0.61、44.83±4.23和22.27±0.15μM，与铅化合物PI-083相比，蛋白酶体的CL和TL活性（IC 50分别 为12.47±0.21、53.12±2.56和26.37±0.5μM）。的抗增殖活性也通过MTT（3-（4

  DOI：

  10.1016/j.ejmech.2020.112890
• 作为产物：
  描述：

  4-溴苯胺 在 吡啶 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 4-amino-N-(4-bromophenyl)benzenesulfonamide
  参考文献：
  名称：

  含氮多羟基芳香族化合物作为HIV-1整合酶抑制剂：合成，构效关系分析和生物活性。

  摘要：

  设计并合成了四种基于咖啡酸苯乙酯的四十五种含氮多羟基化芳烃作为HIV-1整合酶（IN）抑制剂。这些化合物大多数在低微摩尔范围内抑制IN催化活性。在这些新的类似物中，化合物9e和9f是最有效的IN抑制剂，针对链转移反应的IC（50）值为0.7μM。还讨论了它们的关键结构-活性关系。

  DOI：

  10.3109/14756366.2011.604851

文献信息

• Marchant; Lucas; McClelland, Canadian Journal of Research, Section B: Chemical Sciences, 1942, vol. 20, p. 5,7, 9
  作者：Marchant、Lucas、McClelland

  DOI：——

  日期：——
• Design and synthesis of novel nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors from caffeic acid phenethyl ester
  作者：Peng Wang、Chuan Liu、Tino Sanches、Yuan Zhong、Bo Liu、Junlong Xiong、Nouri Neamati、Guisen Zhao

  DOI：10.1016/j.bmcl.2009.06.100

  日期：2009.8

  A series of nitrogen-containing polyhydroxylated aromatics from caffeic acid phenethyl ester were designed and synthesized as HIV-1 integrase inhibitors. Most of these compounds exhibited potent inhibitory activities at micromolar concentrations against HIV-1 integrase in the 3'-end processing and the strand transfer. Their key structure-activity relationship was also discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and anticonvulsant activity of sulfonamide derivatives-hydrophobic domain
  作者：Nadeem Siddiqui、Surendra N. Pandeya、Suroor A. Khan、James Stables、Arpana Rana、Mahfuz Alam、Md. Faiz Arshad、Mashooq A. Bhat

  DOI：10.1016/j.bmcl.2006.09.053

  日期：2007.1

  A series of sulphonamide derivatives (1-11) were synthesized in good yield and evaluated for their possible anticonvulsant activity and neurotoxic study. The structures of the synthesized compounds were confirmed on the basis of their spectral data and elemental analysis. Majority of the compounds were active in MES and scPTZ tests. All the compounds were less toxic than the standard drug phenytoin. (c) 2006 Elsevier Ltd. All rights reserved.
• Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors
  作者：Xiaoxia Zheng、Hiroyuki Oda、Kayo Takamatsu、Yukio Sugimoto、Akihiro Tai、Eiichi Akaho、Hamed Ismail Ali、Toshiyuki Oshiki、Hiroki Kakuta、Kenji Sasaki

  DOI：10.1016/j.bmc.2006.10.029

  日期：2007.1

  In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the anilino moiety, showed COX-1-selective inhibition. Moreover compound 11f, which is the most potent compound in this study showed more potent analgesic activity than that of aspirin at 30 mg/kg by po. The anti-inflammatory activity and gastric damage, however, were very weak or not detectably different from aspirin. Since the structure of our COX-1 inhibitors are very simple, they may be useful as lead compounds for superior COX-1 inhibitors as analgesic agents without gastric disturbance. (c) 2006 Published by Elsevier Ltd.
• Design, synthesis and biological evaluation of novel naphthoquinone-4-aminobenzensulfonamide/carboxamide derivatives as proteasome inhibitors
  作者：Sirin Uysal、Zeynep Soyer、Merve Saylam、Ayse H. Tarikogullari、Sinem Yilmaz、Petek Ballar Kirmizibayrak

  DOI：10.1016/j.ejmech.2020.112890

  日期：2021.1

  A series of novel 4-aminobenzensulfonamide/carboxamide derivatives bearing naphthoquinone pharmacophore were designed, sythesized and evaluated for their proteasome inhibitory and antiproliferative activities against human breast cancer cell line (MCF-7). The structures of the synthesized compounds were confirmed by spectral and elemental analyses. The proteasome inhibitory activity studies were carried

  设计，合成和评估了一系列带有萘醌药效团的新颖的4-氨基苯磺酰胺/羧酰胺衍生物，它们对人乳腺癌细胞系（MCF-7）的蛋白酶体抑制和抗增殖活性。通过光谱和元素分析证实了合成化合物的结构。使用基于细胞的测定法进行蛋白酶体抑制活性的研究。抗蛋白酶体活性结果表明，大多数化合物对半胱天冬酶样（CL，β1亚基），胰蛋白酶样（TL，β2亚基）和胰凝乳蛋白酶样（ChT-L，β5亚基）活性具有不同百分比的抑制活性。蛋白酶体。在测试的化合物中，化合物14在磺酰胺基团的氮原子上带有5-氯-2-吡啶基环的化合物是该系列中活性最高的化合物，显示出更高的抑制作用，对ChT-L的IC 50值为9.90±0.61、44.83±4.23和22.27±0.15μM，与铅化合物PI-083相比，蛋白酶体的CL和TL活性（IC 50分别 为12.47±0.21、53.12±2.56和26.37±0.5μM）。的抗增殖活性也通过MTT（3-（4