ethyl 3-(o-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylate | 1034378-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-(o-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylate
• 英文别名: ethyl 3-(2-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylate
• CAS: 1034378-79-4
• 化学式: C₁₃H₁₃ClN₂O₂
• 分子量: 264.711
• InChiKey: VXXNNQMHHGRJTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(o-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylate 在 三溴化硼 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4-(2-chloro-4-nitrophenyl)piperazin-1-yl)(3-(2-chlorophenyl)-5-methyl-1H-pyrazol-4-yl)methanone
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Biological Evaluation of 1H-1,2,3-Triazole-4-carboxamide Derivatives as New Anti-influenza A Agents Targeting Virus Nucleoprotein

  摘要：

  The influenza virus nucleoprotein (NP) is an emerging target for anti-influenza drug development. Nucleozin (1) and its closely related derivatives had been identified as NP inhibitors displaying anti-influenza activity. Utilizing 1 as a lead molecule, we successfully designed and synthesized a series of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents. One of the most potent compounds, 3b, inhibited the replication of various H3N2 and H1N1 influenza A virus strains with IC50 values ranging from 0.5 to 4.6 mu M. Compound 3b also strongly inhibited the replication of H5N1 (RG14), amantidine-resistant A/WSN/33 (H1N1), and oseltamivir-resistant A/WSN/1933 (H1N1, 274Y) virus strains with IC50 values in sub-mu M ranges. Further computational studies and mechanism investigation suggested that 3b might directly target influenza virus A nucleoprotein to inhibit its nuclear accumulation.

  DOI：

  10.1021/jm2013503
• 作为产物：
  描述：

  ethyl 2-(2-chlorobenzoyl)-3-oxobutanoate 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 ethyl 3-(o-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Biological Evaluation of 1H-1,2,3-Triazole-4-carboxamide Derivatives as New Anti-influenza A Agents Targeting Virus Nucleoprotein

  摘要：

  The influenza virus nucleoprotein (NP) is an emerging target for anti-influenza drug development. Nucleozin (1) and its closely related derivatives had been identified as NP inhibitors displaying anti-influenza activity. Utilizing 1 as a lead molecule, we successfully designed and synthesized a series of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents. One of the most potent compounds, 3b, inhibited the replication of various H3N2 and H1N1 influenza A virus strains with IC50 values ranging from 0.5 to 4.6 mu M. Compound 3b also strongly inhibited the replication of H5N1 (RG14), amantidine-resistant A/WSN/33 (H1N1), and oseltamivir-resistant A/WSN/1933 (H1N1, 274Y) virus strains with IC50 values in sub-mu M ranges. Further computational studies and mechanism investigation suggested that 3b might directly target influenza virus A nucleoprotein to inhibit its nuclear accumulation.

  DOI：

  10.1021/jm2013503

文献信息

• Synthesis and discovery of a novel pyrazole derivative as an inhibitor of apoptosis through modulating integrin β4, ROS, and p53 levels in vascular endothelial cells
  作者：Bao-Xiang Zhao、Lu Zhang、Xing-Shang Zhu、Mao-Sheng Wan、Jing Zhao、Yun Zhang、Shang-Li Zhang、Jun-Ying Miao

  DOI：10.1016/j.bmc.2008.03.011

  日期：2008.5

  Recently, pyrazole derivatives as high affinity and selective A2A adenosine receptor antagonists have been reported. But, so far, there are no reports about the inhibitory effects of multi-substituted pyrazole derivatives on apoptosis of vascular endothelial cells (VECs). In this study, we synthesized six pyrazole derivatives and characterized the structures of the compounds by IR, H-1 NMR, mass spectroscopy, and element analysis. The biology assay showed that a novel pyrazole derivative, ethyl 3-(o-chlorophenyl)-5- methyl-1-phenyl-1H-pyrazole-4-carboxylate (MPD) at low concentration (25 mu M) increased VECs viability and inhibited VECs apoptosis induced by deprivation of serum and FGF-2. During this process, the levels of integrin beta 4, reactive oxygen species (ROS), and p53 were depressed obviously. The data suggested that MPD was a potential inhibitor of apoptosis associated with the signal pathway mediated by integrin beta 4, ROS, and p53 in VECs. (C) 2008 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and in Vitro Biological Evaluation of 1<i>H</i>-1,2,3-Triazole-4-carboxamide Derivatives as New Anti-influenza A Agents Targeting Virus Nucleoprotein
  作者：Huimin Cheng、Junting Wan、Meng-I Lin、Yingxue Liu、Xiaoyun Lu、Jinsong Liu、Yong Xu、Jianxin Chen、Zhengchao Tu、Yih-Shyun E. Cheng、Ke Ding

  DOI：10.1021/jm2013503

  日期：2012.3.8

  The influenza virus nucleoprotein (NP) is an emerging target for anti-influenza drug development. Nucleozin (1) and its closely related derivatives had been identified as NP inhibitors displaying anti-influenza activity. Utilizing 1 as a lead molecule, we successfully designed and synthesized a series of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents. One of the most potent compounds, 3b, inhibited the replication of various H3N2 and H1N1 influenza A virus strains with IC50 values ranging from 0.5 to 4.6 mu M. Compound 3b also strongly inhibited the replication of H5N1 (RG14), amantidine-resistant A/WSN/33 (H1N1), and oseltamivir-resistant A/WSN/1933 (H1N1, 274Y) virus strains with IC50 values in sub-mu M ranges. Further computational studies and mechanism investigation suggested that 3b might directly target influenza virus A nucleoprotein to inhibit its nuclear accumulation.