2-(4-bromophenylsulfanyl)-5-nitrobenzenesulfonamide | 337469-38-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(4-bromophenylsulfanyl)-5-nitrobenzenesulfonamide
• 英文别名: 2-(4-Bromophenyl)sulfanyl-5-nitrobenzenesulfonamide
• CAS: 337469-38-2
• 化学式: C₁₂H₉BrN₂O₄S₂
• 分子量: 389.25
• InChiKey: AYBRTVVSGFLCHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenylsulfanyl)-5-nitrobenzenesulfonamide 在 sodium hydroxide 、 溴 作用下， 以 甲醇 、 水 为溶剂， 生成 3-(4-bromophenyl)-6-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide
  参考文献：
  名称：

  Benzo- and azabenzodithiazole compounds

  摘要：

  本发明提供了公式I的化合物或其药学上可接受的盐、溶剂化物、前药或异构体以及公式的化合物或其药学上可接受的盐、溶剂化物、前药或异构体。本发明的化合物通过抑制HER1、HER2和HER4等生长因子受体的酪氨酸激酶活性，因此可作为抗增殖剂使用。这些化合物还可用于治疗与通过生长因子受体进行信号转导途径相关的其他疾病。

  公开号：

  US20050101646A1
• 作为产物：
  描述：

  4-硝基苯胺-2-磺酸钠 在 盐酸 、 potassium phosphate 、 copper(l) iodide 、 氯化亚砜 、 新铜试剂 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 2-(4-bromophenylsulfanyl)-5-nitrobenzenesulfonamide
  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

文献信息

• 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
  作者：Chien-Shu Chen、Chen-Ming Tan、Chiung-Hua Huang、Ling-Chu Chang、Jih-Pyang Wang、Fong-Chi Cheng、Ji-Wang Chern

  DOI：10.1016/j.bmc.2009.12.008

  日期：2010.1

  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.