4-(4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)benzenesulfonamide | 1454891-17-8

• 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-(4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)benzenesulfonamide
• 英文别名: 4-(4,5,6,7-Tetrabromo-1,3-dioxoisoindol-2-yl)benzenesulfonamide；4-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)benzenesulfonamide
• CAS: 1454891-17-8
• 化学式: C₁₄H₆Br₄N₂O₄S
• 分子量: 617.895
• InChiKey: WDPLKAKJYRNGBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• 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：

  四溴苯酐 、 磺胺 在 溶剂黄146 作用下， 反应 20.0h， 以91%的产率得到4-(4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  [EN] BENZO-HETEROCYCLIC COMPOUNDS AND THEIR APPLICATIONS
  [FR] COMPOSÉS BENZO-HÉTÉROCYCLIQUES ET LEURS APPLICATIONS

  摘要：

  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。

  公开号：

  WO2016041511A1

文献信息

• 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.
• [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。