1-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carboxylic acid | 116834-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carboxylic acid
• 英文别名: 1-(4-chlorophenyl)-5-pyrrol-1-ylpyrazole-4-carboxylic acid
• CAS: 116834-09-4
• 化学式: C₁₄H₁₀ClN₃O₂
• mdl: MFCD01693538
• 分子量: 287.705
• InChiKey: HWWYVSVKEVBRET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对氯苯胺 、 1-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carboxylic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到N,1-bis(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carboxamide
  参考文献：
  名称：

  New 1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides inhibit hepatitis C virus replication via suppression of cyclooxygenase-2

  摘要：

  We report here the synthesis and mechanism of inhibition of pyrazolecarboxamide derivatives as a new class of HCV inhibitors. Compounds 6, 7, 8 and 16 inhibited the subgenomic HCV replicon lb genotype at EC50 values between 5 and 8 mu M and displayed an even higher potency against the infectious Jc1 HCV 2a genotype. Compound 6 exhibited an EC50 of 6.7 mu M and selectivity index of 23 against HCV 1b, and reduced the RNA copies of the infectious Jc1 chimeric 2a clone by 82% at 7 mu M. Evaluation of the mode of anti-HCV activity of 6 revealed that it suppressed HCV-induced COX-2 mRNA and protein expression, displaying an IC50 of 3.2 mu M in COX-2 promoter-linked luciferase reporter assay. Conversely, the anti-HCV activity of 6 was abrogated upon over-expression of COX-2. These findings suggest that 6 as a representative of these pyrazolecarboxamides function as anti-HCV agents via targeting COX-2 at both the transcription and translation levels. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.042
• 作为产物：
  描述：

  5-氨基-1-(4-氯苯基)-1H-吡唑-4-羧酸乙酯 在 氢氧化钾 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 2.25h， 生成 1-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  Corelli; Massa; Stefancich, Farmaco, Edizione Scientifica, 1988, vol. 43, # 3, p. 251 - 265

  摘要：

  DOI：

文献信息

• CORELLI, F.;MASSA, S.;STEFANCICH, G.;SILVESTRI, R.;ARTICO, M.;PANTALEONI,+, FARMACO. ED. SCI., 43,(1988) N 3, C. 251-265
  作者：CORELLI, F.、MASSA, S.、STEFANCICH, G.、SILVESTRI, R.、ARTICO, M.、PANTALEONI,+

  DOI：——

  日期：——
• New 1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides inhibit hepatitis C virus replication via suppression of cyclooxygenase-2
  作者：Dinesh Manvar、Sveva Pelliccia、Giuseppe La Regina、Valeria Famiglini、Antonio Coluccia、Anna Ruggieri、Simona Anticoli、Jin-Ching Lee、Amartya Basu、Ozge Cevik、Lucia Nencioni、Anna Teresa Palamara、Claudio Zamperini、Maurizio Botta、Johan Neyts、Pieter Leyssen、Neerja Kaushik-Basu、Romano Silvestri

  DOI：10.1016/j.ejmech.2014.11.042

  日期：2015.1

  We report here the synthesis and mechanism of inhibition of pyrazolecarboxamide derivatives as a new class of HCV inhibitors. Compounds 6, 7, 8 and 16 inhibited the subgenomic HCV replicon lb genotype at EC50 values between 5 and 8 mu M and displayed an even higher potency against the infectious Jc1 HCV 2a genotype. Compound 6 exhibited an EC50 of 6.7 mu M and selectivity index of 23 against HCV 1b, and reduced the RNA copies of the infectious Jc1 chimeric 2a clone by 82% at 7 mu M. Evaluation of the mode of anti-HCV activity of 6 revealed that it suppressed HCV-induced COX-2 mRNA and protein expression, displaying an IC50 of 3.2 mu M in COX-2 promoter-linked luciferase reporter assay. Conversely, the anti-HCV activity of 6 was abrogated upon over-expression of COX-2. These findings suggest that 6 as a representative of these pyrazolecarboxamides function as anti-HCV agents via targeting COX-2 at both the transcription and translation levels. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Corelli; Massa; Stefancich, Farmaco, Edizione Scientifica, 1988, vol. 43, # 3, p. 251 - 265
  作者：Corelli、Massa、Stefancich、Silvestri、Artico、Pantaleoni、Palumbo、Fanini、Giorgi

  DOI：——

  日期：——