2-iodo-5-nitrobenzenesulfonamide | 1215268-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-iodo-5-nitrobenzenesulfonamide
• 英文别名: 2-Iodo-5-nitrobenzenesulfonamide
• CAS: 1215268-39-5
• 化学式: C₆H₅IN₂O₄S
• 分子量: 328.087
• InChiKey: PDZISUOYZCAQIV-UHFFFAOYSA-N

物化性质

• 熔点：
  187 °C
• 沸点：
  471.7±55.0 °C(Predicted)
• 密度：
  2.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-iodo-5-nitrobenzenesulfonamide 在 potassium phosphate 、 copper(l) iodide 、 新铜试剂 、 溴 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 8.5h， 生成 3-(4-ethylphenyl)-6-nitro-1,3,2-benzodithiazolium ylide 1,1-dioxide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of benzo[1.3.2]dithiazolium ylide 1,1-dioxide derivatives as potential dual cyclooxygenase-2/5-lipoxygenase inhibitors

  摘要：

  3-(4-Bromophenyl)-6-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide (5) was discovered as a new prototype for dual inhibitors of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX). Thus, the structure-activity relationships of benzo[1.3.2]dithiazolium ylide 1,1-dioxide skeleton were carried out. The 6-NO2 group played an essential role in the inhibitory activity. In addition, moderate-sized lipophilic substituents at the para-position of the 3-aryl moiety were required for dual COX-2/5-LOX inhibitory activity. Among the identified potent dual inhibitors, 3-(4-tbutylphenyl) derivative 30c (IC50 values of 0.27 mu M and 0.30 mu M against COX-2 and 5-LOX, respectively) and 3-(4-biphenyl) derivative 30f (IC50 values of 0.50 mu M and 0.15 mu M against COX-2 and 5-LOX, respectively) were the most potent dual COX-2/5-LOX inhibitors. Intraperitoneal administration of 30c at 100 mg/kg demonstrated potent acute anti-inflammatory activity. As a result, benzo[1.3.2]dithiazolium ylide 1,1-dioxide represented a novel scaffold for the exploitation in developing dual COX-2/5-LOX inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.003
• 作为产物：
  描述：

  2-iodo-5-nitrobenzene-1-sulfonyl chloride 在 ammonium hydroxide 作用下， 反应 6.0h， 生成 2-iodo-5-nitrobenzenesulfonamide
  参考文献：
  名称：

  Discovery of 3-(4-bromophenyl)-6-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide as a novel dual cyclooxygenase/5-lipoxygenase inhibitor that also inhibits tumor necrosis factor-α production

  摘要：

  In the present study we have discovered compound 1, a benzo[1.3.2]dithiazolium ylide-based compound, as a new prototype dual inhibitor of cyclooxygenase (COX) and 5-lipoxygenase (5-LOX). Compound 1 was initially discovered as a COX-2 inhibitor, resulting indirectly from the COX-2 structure-based virtual screening that identified compound 2 as a virtual hit. Compounds 1 and 2 inhibited COX-1 and COX-2 in mouse macrophages with IC50 in the range of 1.5-18.1 mu M. Both compounds 1 and 2 were also found to be potent inhibitors of human 5-LOX (IC50 = 1.22 and 0.47 mu M, respectively). Interestingly, compound 1 also had an inhibitory effect on tumor necrosis factor-alpha (TNF-alpha) production (IC50 = 0.44 mu M), which was not observed with compound 2. Docking studies suggested the (S)-enantiomer of 1 as the biologically active isomer that binds to COX-2. Being a cytokine-suppressive dual COX/5-LOX inhibitor, compound 1 may represent a useful lead structure for the development of advantageous new anti-inflammatory agents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.008

文献信息

• Microwave-Assisted Cross-Coupling for the Construction of Diaryl Sulfides
  作者：Chen-Ming Tan、Grace Shiahuy Chen、Chien-Shu Chen、Ji-Wang Chern

  DOI：10.1002/jccs.201190064

  日期：2011.2

  construction of diaryl sulfides through the cross‐coupling of aryl iodides and thiols in microwave heating is described. By using this method, a variety of diaryl sulfides can be prepared in a mild condition and in high yields. Deactivated 4‐nitrothiophenol was effective to afford the product in 94% yield. Sterically hindered ortho‐substituted aryl iodides or thiophenols provided diaryl sulfides effectively

  描述了在微波加热中通过芳基碘化物和硫醇的交叉偶联来构建二芳基硫醚。通过使用这种方法，可以在温和的条件下以高收率制备各种二芳基硫醚。失活的4-硝基硫代苯酚可有效地以94％的收率提供产品。通过微波辅助的偶联反应，受位阻的邻位取代的芳基碘化物或苯硫酚可有效地提供二芳基硫化物。