4-(2-(5-nitro-1,3-dioxoisoindolin-2-yl)ethyl)benzenesulfonamide | 1571901-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-(2-(5-nitro-1,3-dioxoisoindolin-2-yl)ethyl)benzenesulfonamide
• 英文别名: 4-[2-(5-Nitro-1,3-dioxoisoindol-2-yl)ethyl]benzenesulfonamide；4-[2-(5-nitro-1,3-dioxoisoindol-2-yl)ethyl]benzenesulfonamide
• CAS: 1571901-34-2
• 化学式: C₁₆H₁₃N₃O₆S
• 分子量: 375.362
• InChiKey: NGYUNTRTFWIHLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-硝基邻苯二甲酸酐 、 4-(2-氨乙基)苯磺酰胺 在 溶剂黄146 作用下， 反应 12.0h， 生成 4-(2-(5-nitro-1,3-dioxoisoindolin-2-yl)ethyl)benzenesulfonamide
  参考文献：
  名称：

  含苯磺酰胺部分作为碳酸酐酶I，II，IV和IX抑制剂的环状酰亚胺的合成和生物学评估

  摘要：

  通过氨基取代的苯磺酰胺与一系列酸酐如琥珀酸，马来酸，四氢邻苯二甲酸，吡嗪-2，3-二羧酸酐和取代的邻苯二甲酸酐反应，合成一组环状酰亚胺。评估合成的磺酰胺为抗人（h）亚型hCA I，II，IV和IX的碳酸酐酶（CA，EC 4.2.1.1）抑制剂，涉及多种疾病，其中包括青光眼，色素性视网膜炎等。这些磺酰胺类药物对细胞质亚型hCA II和跨膜，与肿瘤相关的一种hCA IX具有有效的抑制作用（在纳摩尔范围内），使其成为青光眼或涉及这两种酶的各种肿瘤的临床前评估的有趣候选药物。

  DOI：

  10.1016/j.bmc.2017.01.032

文献信息

• Carbonic anhydrase inhibitors: Synthesis and inhibition of the human carbonic anhydrase isoforms I, II, IX and XII with benzene sulfonamides incorporating 4- and 3-nitrophthalimide moieties
  作者：Kalyan K. Sethi、Saurabh M. Verma、Muhammet Tanç、Gaultier Purper、Gaetan Calafato、Fabrizio Carta、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2014.01.031

  日期：2014.3

  A series of 4 and 5 nitro-1,3-dioxoisoindolin-2-yl benzenesulfonamide derivatives (compounds 1-8) was synthesized by reaction of benzenesulfonamide derivatives with 4 and 3-nitrophthalic anhydrides. 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 and II and the transmembrane, tumor-associated hCA IX and XII. Most of the novel compounds were medium potency-weak hCA I inhibitors (K(i)s in the range of 295-10,000 nM), but were more effective hCA II inhibitors (K(i)s of 1.7-887 nM). The tumor-associated hCA IX was also inhibited, with K(i)s in the micromolar range, whereas against hCA XII the inhibition constants were in the range of 90-3746 nM. 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 studies was performed in order to rationalize the activities reported and binding mode to different hCA as inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of cyclic imides incorporating benzenesulfonamide moieties as carbonic anhydrase I, II, IV and IX inhibitors
  作者：Alaa A.-M. Abdel-Aziz、Andrea Angeli、Adel S. El-Azab、Mohamed A. Abu El-Enin、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2017.01.032

  日期：2017.3

  group of cyclic imides was synthesized by reaction of amino-substituted benzenesulfonamides with a series of acid anhydrides such as succinic, maleic, tetrahydrophthalic, pyrazine-2,3-dicarboxylic acid anhydride, and substituted phthalic anhydrides. The synthesized sulfonamides were evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors against the human (h) isoforms hCA I, II, IV and IX, involved

  通过氨基取代的苯磺酰胺与一系列酸酐如琥珀酸，马来酸，四氢邻苯二甲酸，吡嗪-2，3-二羧酸酐和取代的邻苯二甲酸酐反应，合成一组环状酰亚胺。评估合成的磺酰胺为抗人（h）亚型hCA I，II，IV和IX的碳酸酐酶（CA，EC 4.2.1.1）抑制剂，涉及多种疾病，其中包括青光眼，色素性视网膜炎等。这些磺酰胺类药物对细胞质亚型hCA II和跨膜，与肿瘤相关的一种hCA IX具有有效的抑制作用（在纳摩尔范围内），使其成为青光眼或涉及这两种酶的各种肿瘤的临床前评估的有趣候选药物。