4-(2-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)ethyl)benzenesulfonamide | 1449762-39-3

• 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-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)ethyl)benzenesulfonamide
• 英文别名: 4-(2-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)ethyl)benzenesulphonamide；4-[2-(4,5,6,7-Tetrachloro-1,3-dioxoisoindol-2-yl)ethyl]benzenesulfonamide；4-[2-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)ethyl]benzenesulfonamide
• CAS: 1449762-39-3
• 化学式: C₁₆H₁₀Cl₄N₂O₄S
• 分子量: 468.144
• InChiKey: GNOITBWORAUPOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 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：
  106
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  四氯苯二甲酸酐 、 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-(4,5,6,7-tetrachloro-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

• 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.