4-amino-2-bromobenzenesulfonamide | 1094798-12-5

• 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-2-bromobenzenesulfonamide
• CAS: 1094798-12-5
• 化学式: C₆H₇BrN₂O₂S
• 分子量: 251.104
• InChiKey: VNBOJTSKUIJYAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四溴苯酐 、 4-amino-2-bromobenzenesulfonamide 在 溶剂黄146 作用下， 反应 12.0h， 以90%的产率得到3-bromo-4-(4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors: Synthesis and inhibition of the human carbonic anhydrase isoforms I, II, VII, IX and XII with benzene sulfonamides incorporating 4,5,6,7-tetrabromophthalimide moiety

  摘要：

  A series of 4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl benzenesulfonamide derivatives (compounds 1-8) was synthesized by reaction of benzene sulfonamide derivatives with 4,5,6,7-tetrabromophthalic anhydride moiety. These new sulfonamides were investigated as inhibitors of the zinc metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) and more specifically against the human (h) cytosolic isoforms hCA I, II and VII and the transmembrane tumor-associated isoform hCA IX and XII. The new compounds were good hCA I inhibitors (Kis in the range of 143 to >10,000 nM), but were moderately effective, as hCA II inhibitors (Kis of 47-190 nM) and poor hCA VII inhibitors (Kis in the range of 54-175 nM) compared to acetazolamide. The tumor-associated hCA IX was effectively inhibited with Kis ranging between 8.5 and 234 nM and hCA XII with inhibition constants in the range of 6.1-197 nM with high selectivity ratio. The structure-activity relationship (SAR) with this series of sulfonamides is straightforward, with the main features leading to good activity for each isoforms being established. The high sequence hCA alignment homology and molecular docking study of compounds was performed to rationalize the SAR reported over here. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.044
• 作为产物：
  描述：

  磺胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75 %的产率得到4-amino-2-bromobenzenesulfonamide
  参考文献：
  名称：

  新型3-溴磺酰胺酰基硫脲衍生物的合成：脲酶抑制及其分子对接研究

  摘要：

  在这项工作中，通过溴化磺酰胺与芳香酸反应形成异硫氰酸酯，设计并合成了基于3-溴磺酰胺基酰基硫脲(4a-j)的具有治疗活性的抗脲酶药物，并使用FT-IR、1HNMR、 13 C NMR和MS分析。筛选新制备的化合物用于体外脲酶抑制测定。与标准硫脲相比，具有未取代苯基的衍生物4a对脲酶的 IC 50值为 17.02 ± 0.011 (IC 50 = 21 ± 0.12 µM)。构效关系（SAR）揭示苯环上取代基的电子和位置效应对于临床重要酶的抑制起着重要作用。此外，进行的计算机研究表明，这些化合物与脲酶结合位点的关键残基表现出极性和非极性相互作用。体外和计算机研究根据动力学和对接结果一致，表明合成的基于 3-溴磺酰胺的酰基硫脲衍生物可能作为发现新脲酶抑制剂的潜在成果。

  DOI：

  10.1007/s13738-024-03076-w

文献信息

• Synthesis and Human Carbonic Anhydrase I, II, IX, and XII Inhibition Studies of Sulphonamides Incorporating Mono-, Bi- and Tricyclic Imide Moieties
  作者：Kalyan Sethi、KM Mishra、Saurabh Verma、Daniela Vullo、Fabrizio Carta、Claudiu Supuran

  DOI：10.3390/ph14070693

  日期：——

  anhydrides. These sulphonamides were investigated as human carbonic anhydrases (hCAs, EC 4.2.1.1) I, II, IX, and XII inhibitors. hCA I was inhibited with inhibition constants (Kis) ranging from 49 to >10,000 nM. The physiologically dominant hCA II was significantly inhibited by most of the sulphonamide with the Kis ranging between 2.4 and 4515 nM. hCA IX and hCA XII were inhibited by these sulphonamides

  新的衍生物是通过含氨基的芳香磺酰胺与单、双和三环酸酐反应合成的。这些磺胺类药物被研究为人类碳酸酐酶 (hCAs, EC 4.2.1.1) I、II、IX 和 XII 抑制剂。hCA I 受到抑制常数 (Kis) 范围从 49 到 >10,000 nM 的抑制。生理上占优势的 hCA II 被大多数磺胺显着抑制，Kis 范围在 2.4 和 4515 nM 之间。hCA IX 和 hCA XII 分别在 9.7 至 7766 nM 和 14 至 316 nM 的范围内被这些磺胺类药物抑制。在分子对接研究的帮助下，结构-活性关系（SAR）被合理化。
• Carbonic anhydrase inhibitors: Synthesis and inhibition of the cytosolic mammalian carbonic anhydrase isoforms I, II and VII with benzene sulfonamides incorporating 4,5,6,7-tetrachlorophthalimide moiety
  作者：Kalyan K. Sethi、Saurabh M. Verma、Muhammet Tanç、Fabrizio Carta、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2013.06.035

  日期：2013.9

  A series of 4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl benzenesulfonamide derivatives (compounds 1-8) was synthesized by reaction of benzene sulfonamides incorporating primary amino moieties with 4,5,6,7-tetrachlorophthalic anhydride. These sulfonamides were assayed as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Some of these compounds showed very good in vitro human carbonic anhydrase (hCA) isoforms I, II and VII inhibitory properties, with affinities in the low nanomolar range. Inhibition activities against hCA I were in the range of 159-444 nM; against hCA II in the range of 2.4-4515 nM, and against hCA VII in the range of 1.3-469 nM. The structure-activity relationship (SAR) with this series of sulfonamides is straightforward, with the main features leading to good activity for each isoform being established. (C) 2013 Elsevier Ltd. All rights reserved.
• US7452873B2
  申请人：——

  公开号：US7452873B2

  公开（公告）日：2008-11-18
• Carbonic anhydrase inhibitors: Synthesis and inhibition of the human carbonic anhydrase isoforms I, II, VII, IX and XII with benzene sulfonamides incorporating 4,5,6,7-tetrabromophthalimide moiety
  作者：Kalyan K. Sethi、Daniella Vullo、Saurabh M. Verma、Muhammet Tanç、Fabrizio Carta、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2013.07.044

  日期：2013.10

  A series of 4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl benzenesulfonamide derivatives (compounds 1-8) was synthesized by reaction of benzene sulfonamide derivatives with 4,5,6,7-tetrabromophthalic anhydride moiety. These new sulfonamides were investigated as inhibitors of the zinc metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) and more specifically against the human (h) cytosolic isoforms hCA I, II and VII and the transmembrane tumor-associated isoform hCA IX and XII. The new compounds were good hCA I inhibitors (Kis in the range of 143 to >10,000 nM), but were moderately effective, as hCA II inhibitors (Kis of 47-190 nM) and poor hCA VII inhibitors (Kis in the range of 54-175 nM) compared to acetazolamide. The tumor-associated hCA IX was effectively inhibited with Kis ranging between 8.5 and 234 nM and hCA XII with inhibition constants in the range of 6.1-197 nM with high selectivity ratio. The structure-activity relationship (SAR) with this series of sulfonamides is straightforward, with the main features leading to good activity for each isoforms being established. The high sequence hCA alignment homology and molecular docking study of compounds was performed to rationalize the SAR reported over here. (C) 2013 Elsevier Ltd. All rights reserved.
• 10.1007/s13738-024-03076-w
  作者：Um-e-Farwa、Ahmed, Atteeque、Saeed, Aamer、Shafique, Imran、Saleem, Muhammad、Hussain, Jabir、Mumtaz, Amara、Rafique, Hummera

  DOI：10.1007/s13738-024-03076-w

  日期：——

  it is designed and synthesized therapeutically active anti-urease agents based on 3-bromosulfanilamide-based acyl thioureas (4a-j) through reaction of brominated sulfanilamide with aromatic acids via isothiocyanate formation and characterized by using FT-IR, 1HNMR, 13C NMR and MS analysis. The freshly prepared compounds were screened for in vitro urease inhibition assay. The derivative 4a with an

  在这项工作中，通过溴化磺酰胺与芳香酸反应形成异硫氰酸酯，设计并合成了基于3-溴磺酰胺基酰基硫脲(4a-j)的具有治疗活性的抗脲酶药物，并使用FT-IR、1HNMR、 13 C NMR和MS分析。筛选新制备的化合物用于体外脲酶抑制测定。与标准硫脲相比，具有未取代苯基的衍生物4a对脲酶的 IC 50值为 17.02 ± 0.011 (IC 50 = 21 ± 0.12 µM)。构效关系（SAR）揭示苯环上取代基的电子和位置效应对于临床重要酶的抑制起着重要作用。此外，进行的计算机研究表明，这些化合物与脲酶结合位点的关键残基表现出极性和非极性相互作用。体外和计算机研究根据动力学和对接结果一致，表明合成的基于 3-溴磺酰胺的酰基硫脲衍生物可能作为发现新脲酶抑制剂的潜在成果。