4-(3-(4-chlorophenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(3-(4-chlorophenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide
• 英文别名: 4-[5-(4-Chlorophenyl)-3-naphthalen-2-yl-3,4-dihydropyrazol-2-yl]benzenesulfonamide；4-[5-(4-chlorophenyl)-3-naphthalen-2-yl-3,4-dihydropyrazol-2-yl]benzenesulfonamide
• 化学式: C₂₅H₂₀ClN₃O₂S
• 分子量: 461.972
• InChiKey: BDBAYMZOFMAWRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-chlorophenyl)-3-(2-naphthalenyl)prop-2-en-1-one 、 4-磺酰胺基苯肼盐酸盐 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以71.3%的产率得到4-(3-(4-chlorophenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Sulfonamide derivatives containing dihydropyrazole moieties selectively and potently inhibit MMP-2/MMP-9: Design, synthesis, inhibitory activity and 3D-QSAR analysis

  摘要：

  New series of sulfonamide derivatives containing a dihydropyrazole moieties inhibitors of MMP-2/MMP-9 were discovered using structure-based drug design. Synthesis, antitumor activity, structure-activity relationship and optimization of physicochemical properties were described. In vitro the bioassay results revealed that most target compounds showed potent inhibitory activity in the enzymatic and cellular assays. Among the compounds, compound 3i exhibited the most potent inhibitory activity with IC50 values of 0.21 mu M inhibiting MMP-2 and 1.87 mu M inhibiting MMP-9, comparable to the control positive compound CMT-1 (1.26 mu M, 2.52 mu M). Docking simulation was performed to position compound 3i into the MMP-2 active site to determine the probable binding pose. Docking simulation was further performed to position compound 3i into the MMP-2 active site to determine the probable binding model the 3D-QSAR models were built for reasonable design of MMP-2/MMP-9 inhibitors at present and in future. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.026

文献信息

• Sulfonamide derivatives containing dihydropyrazole moieties selectively and potently inhibit MMP-2/MMP-9: Design, synthesis, inhibitory activity and 3D-QSAR analysis
  作者：Xiao-Qiang Yan、Zhong-Chang Wang、Zhen Li、Peng-Fei Wang、Han-Yue Qiu、Long-Wang Chen、Xiao-Yuan Lu、Peng-Cheng Lv、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2015.08.026

  日期：2015.10

  New series of sulfonamide derivatives containing a dihydropyrazole moieties inhibitors of MMP-2/MMP-9 were discovered using structure-based drug design. Synthesis, antitumor activity, structure-activity relationship and optimization of physicochemical properties were described. In vitro the bioassay results revealed that most target compounds showed potent inhibitory activity in the enzymatic and cellular assays. Among the compounds, compound 3i exhibited the most potent inhibitory activity with IC50 values of 0.21 mu M inhibiting MMP-2 and 1.87 mu M inhibiting MMP-9, comparable to the control positive compound CMT-1 (1.26 mu M, 2.52 mu M). Docking simulation was performed to position compound 3i into the MMP-2 active site to determine the probable binding pose. Docking simulation was further performed to position compound 3i into the MMP-2 active site to determine the probable binding model the 3D-QSAR models were built for reasonable design of MMP-2/MMP-9 inhibitors at present and in future. (C) 2015 Elsevier Ltd. All rights reserved.