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

中文名称
——
中文别名
——
英文名称
2-iodo-5-nitrobenzenesulfonamide
英文别名
2-Iodo-5-nitrobenzenesulfonamide
2-iodo-5-nitrobenzenesulfonamide化学式
CAS
1215268-39-5
化学式
C6H5IN2O4S
mdl
——
分子量
328.087
InChiKey
PDZISUOYZCAQIV-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    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
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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。
  • Design, synthesis and biological evaluation of benzo[1.3.2]dithiazolium ylide 1,1-dioxide derivatives as potential dual cyclooxygenase-2/5-lipoxygenase inhibitors
    作者:Chen-Ming Tan、Grace Shiahuy Chen、Chien-Shu Chen、Pei-Teh Chang、Ji-Wang Chern
    DOI:10.1016/j.bmc.2011.09.003
    日期:2011.11
    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.
  • 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.
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