4-amino-N-(4-sulfamoylphenyl)benzamide | 4389-05-3

• 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-sulfamoylphenyl)benzamide
• CAS: 4389-05-3
• 化学式: C₁₃H₁₃N₃O₃S
• 分子量: 291.331
• InChiKey: GKFZCIMPMVFMLY-UHFFFAOYSA-N

物化性质

• 熔点：
  313 °C (decomp)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 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：
  124
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  5-甲氧基靛红 、 4-amino-N-(4-sulfamoylphenyl)benzamide 在 溶剂黄146 作用下， 反应 5.0h， 以49%的产率得到4-(5-methoxy-2-oxoindolin-3-ylideneamino)-N-(4-sulfamoylphenyl)benzamide
  参考文献：
  名称：

  Amido/ureidosubstituted benzenesulfonamides-isatin conjugates as low nanomolar/subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform XII

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2016.01.030
• 作为产物：
  描述：

  4-硝基苯甲酰替苯胺 在 chlorosulphuric acid 、 乙醇 、 镍 作用下， 生成 4-amino-N-(4-sulfamoylphenyl)benzamide
  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

• Synthesis of novel sulfonamides under mild conditions with effective inhibitory activity against the carbonic anhydrase isoforms I and II
  作者：Erhan Başar、Ekrem Tunca、Metin Bülbül、Muharrem Kaya

  DOI：10.3109/14756366.2015.1134524

  日期：2016.11.1

  from the reactions of 4-amino-N-(4-sulfamoylphenyl) benzamide 4 and sulfonyl chloride derivatives 5a-i with high yield (71-90%). The structures of these compounds were confirmed by using spectral analysis (FT-IR, (1)H NMR, (13)C NMR, LC/MS and HRMS). The inhibition effects of 6a-i on the hydratase and esterase activities of human carbonic anhydrase isoenzymes, hCA I and II, which were purified from human

  由4-氨基-N-（4-氨磺酰基苯基）苯甲酰胺4与磺酰氯衍生物5a-i的反应高收率合成了新型磺酰胺衍生物6a-i，作为可用于青光眼治疗的新型碳酸酐酶抑制剂（71- 90％）。这些化合物的结构通过光谱分析（FT-IR，（1）H NMR，（13）C NMR，LC / MS和HRMS）确定。研究了6a-i对人类碳酸酐酶同工酶hCA I和II的水合酶和酯酶活性的抑制作用，hCA I和II用Sepharose®4B-1-酪氨酸-对氨基苯磺酰胺亲和色谱法从人红细胞中纯化而来。体外测定IC50和Ki值。结果表明，新合成的化合物具有很强的抑制性能。
• 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.
• Derivatives of Sulfanilamide. I. N⁴-(p-Aminobenzoyl)-sulfanilamide and Related Compounds
  作者：Edith Ju-Hwa Chu

  DOI：10.1021/ja01228a060

  日期：1945.12