3-(2-(3-fluoro-5-(4-(4-methoxytetrahydropyranyl))phenoxy)ethyl)-6-nitro-1,3,2-benzodithiazolium ylide 1,1-dioxide | 1345021-15-9

• 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: 3-(2-(3-fluoro-5-(4-(4-methoxytetrahydropyranyl))phenoxy)ethyl)-6-nitro-1,3,2-benzodithiazolium ylide 1,1-dioxide
• 英文别名: 9-[2-[3-Fluoro-5-(4-methoxyoxan-4-yl)phenoxy]ethyl]-4-nitro-7lambda6,9lambda4-dithia-8-azabicyclo[4.3.0]nona-1(6),2,4,8-tetraene 7,7-dioxide；9-[2-[3-fluoro-5-(4-methoxyoxan-4-yl)phenoxy]ethyl]-4-nitro-7λ6,9λ4-dithia-8-azabicyclo[4.3.0]nona-1(6),2,4,8-tetraene 7,7-dioxide
• CAS: 1345021-15-9
• 化学式: C₂₀H₂₁FN₂O₇S₂
• 分子量: 484.526
• InChiKey: NMEFTPNOZYQBMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-(5-氟-3-羟基苯基)-4-甲氧基-3,4,5,6-四氢-2H-吡喃 在 potassium phosphate 、 copper(l) iodide 、 新铜试剂 、 溴 、 potassium carbonate 、 硫脲 作用下， 以 甲醇 、 乙醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 37.5h， 生成 3-(2-(3-fluoro-5-(4-(4-methoxytetrahydropyranyl))phenoxy)ethyl)-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