4-(1,3-Dioxobenzo[de]isoquinolin-2-yl)benzenesulfonamide | 405270-57-7

• 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)benzenesulfonamide
• CAS: 405270-57-7
• 化学式: C₁₈H₁₂N₂O₄S
• 分子量: 352.37
• InChiKey: MZZZNXUNTMXPRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  656.4±61.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,8-萘二甲酸酐 、 磺胺 在 咪唑 作用下， 以84 %的产率得到4-(1,3-Dioxobenzo[de]isoquinolin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  用于检测硝基苯的基于萘酰亚胺的荧光探针的 AIEE 活性 J 聚集体：非共价相互作用分析的实验和理论相结合的方法

  摘要：

  通过一步酰亚胺化反应合理合成了一种新的基于萘酰亚胺的荧光探针NS，它具有基于 J 聚集体的特殊聚集诱导发光增强 (AIEE) 特性。探针NS通过形成具有显着红移的 J 聚集体，在水性介质中表现出优异的 AIEE 特性。AIEE 活性探针NS用于基于荧光猝灭响应的硝基苯 (NB) 的选择性和灵敏检测。通过荧光滴定评估 J 聚集体的形成。这些 J 聚集体对在探针NS之间产生有利的相互作用做出了重大贡献和注意。NB 的高选择性荧光检测被认可为可调节的较小尺寸的 NB，它可以很容易地渗透到探针分子的间隙空间。传感器检测固态 NB 的能力也通过固态荧光光谱法实现。还通过1研究了 NB探针NS的相互作用性质和灵敏度H NMR 滴定和密度泛函理论 (DFT)，包括非共价相互作用 (NCI)、分子中原子的量子理论 (QTAIM)、电子密度差 (EDD)、前沿分子轨道 (FMO) 和态密度 (DOS) 分析

  DOI：

  10.1016/j.saa.2022.122273

文献信息

• Synthesis and carbonic anhydrase inhibition of polycyclic imides incorporating N-benzenesulfonamide moieties
  作者：Andrea Angeli、Alaa A.-M. Abdel-Aziz、Alessio Nocentini、Adel S. El-Azab、Paola Gratteri、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2017.07.056

  日期：2017.10

  A series of polycyclic imides was prepared by reaction of the benzenesulfonamide with an appropriate polycyclic acid anhydride in refluxing glacial acetic acid. The synthesized mono- and bis-sulfonamides were evaluated as a carbonic anhydrase inhibitors (CA, EC 4.2.1.1), more precisely against the human (h) isoforms hCA I, II, IX and XII, some of which are involved in various pathologies, such as glaucoma

  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。
• [EN] BENZO-HETEROCYCLIC COMPOUNDS AND THEIR APPLICATIONS<br/>[FR] COMPOSÉS BENZO-HÉTÉROCYCLIQUES ET LEURS APPLICATIONS
  申请人：LU YEN-TA

  公开号：WO2016041511A1

  公开（公告）日：2016-03-24

  The present invention relates to benzoxazole derivatives having Formula (I). The compounds of the present invention are found to possess the ability to decrease PD-L1 level, suggesting that the compounds of the invention can be used in cancer immunotherapy and treatment or prevention of sepsis or septic shock.

  本发明涉及具有化学式（I）的苯并噁唑衍生物。本发明的化合物被发现具有降低PD-L1水平的能力，表明本发明的化合物可用于癌症免疫疗法以及用于治疗或预防败血症或脓毒性休克。
• 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.
• EP3194368B1
  申请人：——

  公开号：EP3194368B1

  公开（公告）日：2020-12-23
• BENZO-HETEROCYCLIC COMPOUNDS AND THEIR APPLICATIONS
  申请人：LU YEN-TA

  公开号：US20170283408A1

  公开（公告）日：2017-10-05

  The present invention relates to benzoxazole derivatives having the following Formula (I): The compounds of the present invention are found to possess the ability to decrease PD-L1 level, suggesting that the compounds of the invention can be used in cancer immunotherapy and treatment or prevention of sepsis or septic shock.