N-(4-(氨基磺酰基)苯基)-4-硝基苯甲酰胺 | 19411-48-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-(氨基磺酰基)苯基)-4-硝基苯甲酰胺
• 英文名称: N-(4-(aminosulfonyl)phenyl)-4-nitrobenzamide
• 英文别名: 4-nitro-N-(4-sulfamoylphenyl)benzamide；N-(4-nitro-benzoyl)-sulfanilic acid amide；N-(4-Nitro-benzoyl)-sulfanilsaeure-amid；4-Nitro-benzoesaeure-(4-sulfamoyl-anilid)；N⁴-(p-Nitro-benzoyl)-sulfanilamid
• CAS: 19411-48-4
• 化学式: C₁₃H₁₁N₃O₅S
• mdl: MFCD00272336
• 分子量: 321.313
• InChiKey: BZHGNPUJSLSEPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 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：
  144
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-(氨基磺酰基)苯基)-4-硝基苯甲酰胺 在 sodium azide 、 四氯化硅 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以100%的产率得到1-(4-(aminosulfonyl)phenyl)-5-(4-nitrophenyl)-1H-tetrazole
  参考文献：
  名称：

  Novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors

  摘要：

  A series of novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors was prepared via treatment of various diaryl amides with tetrachlorosilane/sodium azide. All compounds were tested in cyclooxygenase (COX) assays in vitro to determine COX-1 and COX-2 inhibitory potency and selectivity. Tetrazoles contained a methylsulfonyl or sulfonamide group as COX-2 pharmacophore displayed only low inhibitory potency towards COX-2. Most potent compounds showed IC50 values of 6 and 7 mu M for COX-2. All compounds showed IC50 values greater 100 mu M for COX-1 inhibition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.093
• 作为产物：
  描述：

  4-硝基苯甲酰替苯胺 在 chlorosulphuric acid 作用下， 生成 N-(4-(氨基磺酰基)苯基)-4-硝基苯甲酰胺
  参考文献：
  名称：

  磺胺衍生物；N4-（对氨基苯甲酰基）-磺胺及相关化合物。

  摘要：

  DOI：

  10.1021/ja01228a060

文献信息

• Microwave assisted synthesis of novel tetrazole/sulfonamide derivatives based on octahydroacridine, xanthene and chromene skeletons as inhibitors of the carbonic anhydrases isoforms I, II, IV and VII
  作者：İbrahim Esirden、Muhammet Tanç、Claudiu T. Supuran、Muharrem Kaya

  DOI：10.1016/j.bmcl.2016.11.028

  日期：2017.1

  compounds were assayed for the inhibition of carbonic anhydrase (CA, EC 4.2.1.1). The inhibitory activities were determined against three cytosolic human isoforms (hCA I, II and VII) and one membrane-associated (hCA IV) isoform. Some of the newly synthesized sulfonamides showed micromolar to nanomolar inhibitory activity against these enzymes.

  这项研究报道了利用微波（MW）辅助技术合成基于八氢ac啶，and吨和色烯骨架的新型四唑/磺酰胺衍生物。分析了这些合成的杂合化合物对碳酸酐酶的抑制作用（CA，EC 4.2.1.1）。确定了对三种胞质人同工型（hCA I，II和VII）和一种与膜相关的人同工型（hCA IV）的抑制活性。一些新合成的磺酰胺对这些酶表现出微摩尔至纳摩尔的抑制活性。
• Synthesis of novel acridine and bis acridine sulfonamides with effective inhibitory activity against the cytosolic carbonic anhydrase isoforms II and VII
  作者：Ramazan Ulus、İbrahim Yeşildağ、Muhammet Tanç、Metin Bülbül、Muharrem Kaya、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2013.07.014

  日期：2013.9

  4-Amino-N-(4-sulfamoylphenyl)benzamide was synthesized by reduction of 4-nitro-N-(4-sulfamoylphenyl)benzamide and used to synthesize novel acridine sulfonamide compounds, by a coupling reaction with cyclic-1,3-diketones and aromatic aldehydes. The new compounds were investigated as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1), and more precisely the cytosolic isoforms hCA I, II and VII. hCA I was inhibited in the micromolar range by the new compounds (K(i)s of 0.16-9.64 mu M) whereas hCA II and VII showed higher affinity for these compounds, with K(i)s in the range of 15-96 nM for hCA II, and of 4-498 nM for hCA VII. The structure-activity relationships for the inhibition of these isoforms with the acridine-sulfonamides reported here were also elucidated. (C) 2013 Elsevier Ltd. All rights reserved.
• Amido/ureidosubstituted benzenesulfonamides-isatin conjugates as low nanomolar/subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform XII
  作者：Wagdy M. Eldehna、Mohamed Fares、Mariangela Ceruso、Hazem A. Ghabbour、Sahar M. Abou-Seri、Hatem A. Abdel-Aziz、Dalal A. Abou El Ella、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2016.01.030

  日期：2016.3

  By using a molecular hybridization approach, two series of amido/ureidosubstituted benzenesulfonamides incorporating substituted-isatin moieties were synthesized. The prepared derivatives were in vitro evaluated for their inhibitory activity against human carbonic anhydrase (hCA, EC 4.2.1.1) I, II (cytosolic) and IX, XII (transmembrane, tumor-associated) isoforms. All these isoforms were inhibited in variable degrees by the sulfonamides reported here. hCA I was inhibited with K(I)s in the range of 7.9-894 nM, hCA II in the range of 7.5-1645 nM (with one compound having a K-I > 10 mu M); hCA IX in the range of 5.0-240 nM, whereas hCA XII in the range of 0.47-2.83 nM. As all these isoforms are involved in various pathologies, in which their inhibition can be exploited therapeutically, the derivatives reported here may represent interesting extensions to the field of CA inhibitors of the sulfonamide type. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Chemotherapeutic Study of p-Nitrobenzoyl- and Related Compounds
  作者：C. Siebenmann、R. J. Schnitzer

  DOI：10.1021/ja01251a029

  日期：1943.11
• Patel, Navin B.; Patel, Jignesh N.; Lilakar, Jaydeep D., Acta poloniae pharmaceutica, 2010, vol. 67, # 4, p. 351 - 359
  作者：Patel, Navin B.、Patel, Jignesh N.、Lilakar, Jaydeep D.

  DOI：——

  日期：——