3-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)acrylic acid | 1390681-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)acrylic acid
• CAS: 1390681-80-7
• 化学式: C₁₈H₁₃N₃O₄
• 分子量: 335.319
• InChiKey: FNWKBNAVMWTQMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.26
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)acrylic acid 、 甲氧苯胺 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以82%的产率得到N-(4-methoxyphenyl)-3-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)acrylamide
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking studies of 3-(1,3-diphenyl-1H-pyrazol-4-yl)-N-phenylacrylamide derivatives as inhibitors of HDAC activity

  摘要：

  In present study, a series of 3-(1,3-diphenyl-1H-pyrazol-4-yl)-N-phenylacrylamide derivatives (5a-8d) were designed, synthesized, and evaluated for HDAC inhibition and tumor cell antiproliferation. All of these compounds are reported for the first time, the chemical structures of these compounds were confirmed by means of H-1 NMR, ESI-MS and elemental analyzes. Among the compounds, compound 8c showed the most potent biological activity against HCT116 cancer cell line (IC50 of 0.42 +/- 0.02 mu M for HDAC-1 and IC50 = 0.62 +/- 0.02 for HCT116). Docking simulation was performed to position compound 8c into the HDAC active site to determine the probable binding model. The results of antiproliferative assay and western-blot demonstrated that compound 8c with potent inhibitory activity in tumor growth inhibition may be a potential anticancer agent against HCT116 cancer cell. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.031
• 作为产物：
  描述：

  1-(4-nitro-phenyl)-ethanone-phenylhydrazone 在 哌啶 、 吡啶 、 三氯氧磷 作用下， 反应 5.0h， 生成 3-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)acrylic acid
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking studies of 3-(1,3-diphenyl-1H-pyrazol-4-yl)-N-phenylacrylamide derivatives as inhibitors of HDAC activity

  摘要：

  In present study, a series of 3-(1,3-diphenyl-1H-pyrazol-4-yl)-N-phenylacrylamide derivatives (5a-8d) were designed, synthesized, and evaluated for HDAC inhibition and tumor cell antiproliferation. All of these compounds are reported for the first time, the chemical structures of these compounds were confirmed by means of H-1 NMR, ESI-MS and elemental analyzes. Among the compounds, compound 8c showed the most potent biological activity against HCT116 cancer cell line (IC50 of 0.42 +/- 0.02 mu M for HDAC-1 and IC50 = 0.62 +/- 0.02 for HCT116). Docking simulation was performed to position compound 8c into the HDAC active site to determine the probable binding model. The results of antiproliferative assay and western-blot demonstrated that compound 8c with potent inhibitory activity in tumor growth inhibition may be a potential anticancer agent against HCT116 cancer cell. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.031