3-(4-bromophenyl)-5-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide | 485318-56-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-(4-bromophenyl)-5-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide
• 英文别名: 1-(4-Bromophenyl)-6-nitro-1lambda~4~,3,2-benzodithiazole 3,3-dioxide；9-(4-bromophenyl)-3-nitro-7λ6,9λ4-dithia-8-azabicyclo[4.3.0]nona-1(6),2,4,8-tetraene 7,7-dioxide
• CAS: 485318-56-7
• 化学式: C₁₂H₇BrN₂O₄S₂
• 分子量: 387.235
• InChiKey: QZUCRZKNXXRCTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(4-bromophenylsulfanyl)-4-nitrobenzenesulfonamide 在 溴 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以56%的产率得到3-(4-bromophenyl)-5-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide
  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

• 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.