4-[(1,3-Dioxobenzo[de]isoquinolin-2-yl)methyl]benzenesulfonamide | 1429784-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-[(1,3-Dioxobenzo[de]isoquinolin-2-yl)methyl]benzenesulfonamide
• 英文别名: 4-[(1,3-dioxobenzo[de]isoquinolin-2-yl)methyl]benzenesulfonamide
• CAS: 1429784-85-9
• 化学式: C₁₉H₁₄N₂O₄S
• 分子量: 366.397
• InChiKey: CNFAHVNPEUHGNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  磺胺米隆 、 1,8-萘二甲酸酐 在 sodium acetate 、 溶剂黄146 作用下， 反应 12.0h， 以91%的产率得到4-[(1,3-Dioxobenzo[de]isoquinolin-2-yl)methyl]benzenesulfonamide
  参考文献：
  名称：

  含N-苯磺酰胺基团的多环酰亚胺的合成及其碳酸酐酶抑制作用

  摘要：

  通过使苯磺酰胺与适当的多环酸酐在回流的冰醋酸中反应来制备一系列多环酰亚胺。合成的单磺酰胺和双磺酰胺被评估为碳酸酐酶抑制剂（CA，EC 4.2.1.1），更准确地针对人（h）亚型hCA I，II，IX和XII，其中一些涉及多种病理如青光眼，癫痫和癌症。检测了几种低纳摩尔浓度和同工型选择性的hCA II，IX和XII抑制剂，并详细讨论了用此类化合物抑制CA的构效关系。计算研究使我们能够解释其中某些酶抑制剂的功效和同工型选择性行为。

  DOI：

  10.1016/j.bmc.2017.07.056

文献信息

• Molecular design, synthesis and biological evaluation of cyclic imides bearing benzenesulfonamide fragment as potential COX-2 inhibitors. Part 2
  作者：Ibrahim A. Al-Suwaidan、Amer M. Alanazi、Adel S. El-Azab、Abdulrahman M. Al-Obaid、Kamal E.H. ElTahir、Azza R. Maarouf、Mohamed A. Abu El-Enin、Alaa A.-M. Abdel-Aziz

  DOI：10.1016/j.bmcl.2013.02.107

  日期：2013.5

  A group of cyclic imides (1-10) was designed for evaluation as a selective COX-2 inhibitors and investigated in vivo for their anti-inflammatory activity. Compounds 6a, 6b, 8a, 8b, 9a, 9b, 10a and 10b were proved to be potent COX-2 inhibitors with IC50 range of 0.1-4.0 mu M. In vitro COX-1/COX-2 inhibition structure-activity studies identified compound 8a as a highly potent (IC50 = 0.1 mu M), and an extremely selective [COX-2 (SI) > 1000] comparable to celecoxib [COX-2 (SI) > 384], COX-2 inhibitor that showed superior anti-inflammatory activity (ED50 = 72.4 mg/kg) relative to diclofenac (ED50 = 114 mg/kg). Molecular modeling was carried out through docking the designed compounds into the COX-2 binding site to predict if these compounds have analogous binding mode to the COX-2 inhibitors. The study showed that the homosulfonamide fragment of 8a inserted deep inside the 2 degrees-pocket of the COX-2 active site, where the SO2NH2 group underwent H-bonding interaction with Gln(192)(2.95 angstrom), Phe(518)(2.82 angstrom) and Arg(513)(2.63 and 2.73 angstrom). Docking study of the synthesized compound 8a into the active site of COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.