N-phenyl-3-(p-fluorophenyl)-4-(1-p-bromophenyl-2-propen-1-one-3-yl)pyrazole | 1356031-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-phenyl-3-(p-fluorophenyl)-4-(1-p-bromophenyl-2-propen-1-one-3-yl)pyrazole
• 英文别名: (Z)-1-(4-bromophenyl)-3-[3-(4-fluorophenyl)-1-phenylpyrazol-4-yl]prop-2-en-1-one
• CAS: 1356031-93-0
• 化学式: C₂₄H₁₆BrFN₂O
• 分子量: 447.306
• InChiKey: MRZUPLUCUZMNJK-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenyl-3-(p-fluorophenyl)-4-(1-p-bromophenyl-2-propen-1-one-3-yl)pyrazole 在 一水合肼 作用下， 反应 8.0h， 以64%的产率得到N-phenyl-3-(p-fluorophenyl)-4-[3-(p-bromophenyl)pyrazoline-5-yl]pyrazole
  参考文献：
  名称：

  Synthesis, antitubercular evaluation and 3D-QSAR study of N-phenyl-3-(4-fluorophenyl)-4-substituted pyrazole derivatives

  摘要：

  As a part of our ongoing research to develop novel antitubercular agents, a series of N-phenyl-3-(4-fluorophenyl)-4-substituted pyrazoles have been synthesized and tested for antimycobacterial activity in vitro against Mycobacterium tuberculosis H37Rv strain using the BACTEC 460 radiometric system. A 3D-QSAR study based on CoMFA and CoMSIA was performed on these pyrazole derivatives to correlate their chemical structures with the observed activity against M. tuberculosis. The CoMFA model provided a significant correlation of steric and electrostatic fields with the biological activity while the CoMSIA model could additionally shed light on the role of hydrogen bonding and hydrophobic features. The important features identified in the 3D-QSAR models have been used to propose new molecules whose activities are predicted higher than the existing systems. This study provides valuable directions to our ongoing endeavor of rationally designing more potent antitubercular agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.059
• 作为产物：
  描述：

  4-溴苯乙酮 、 3-(4-氟-苯基)-1-苯基-1H-吡唑-4-甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以77%的产率得到N-phenyl-3-(p-fluorophenyl)-4-(1-p-bromophenyl-2-propen-1-one-3-yl)pyrazole
  参考文献：
  名称：

  Synthesis, antitubercular evaluation and 3D-QSAR study of N-phenyl-3-(4-fluorophenyl)-4-substituted pyrazole derivatives

  摘要：

  As a part of our ongoing research to develop novel antitubercular agents, a series of N-phenyl-3-(4-fluorophenyl)-4-substituted pyrazoles have been synthesized and tested for antimycobacterial activity in vitro against Mycobacterium tuberculosis H37Rv strain using the BACTEC 460 radiometric system. A 3D-QSAR study based on CoMFA and CoMSIA was performed on these pyrazole derivatives to correlate their chemical structures with the observed activity against M. tuberculosis. The CoMFA model provided a significant correlation of steric and electrostatic fields with the biological activity while the CoMSIA model could additionally shed light on the role of hydrogen bonding and hydrophobic features. The important features identified in the 3D-QSAR models have been used to propose new molecules whose activities are predicted higher than the existing systems. This study provides valuable directions to our ongoing endeavor of rationally designing more potent antitubercular agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.059

文献信息

• Synthesis, antitubercular evaluation and 3D-QSAR study of N-phenyl-3-(4-fluorophenyl)-4-substituted pyrazole derivatives
  作者：R.C. Khunt、V.M. Khedkar、R.S. Chawda、N.A. Chauhan、A.R. Parikh、E.C. Coutinho

  DOI：10.1016/j.bmcl.2011.10.059

  日期：2012.1

  As a part of our ongoing research to develop novel antitubercular agents, a series of N-phenyl-3-(4-fluorophenyl)-4-substituted pyrazoles have been synthesized and tested for antimycobacterial activity in vitro against Mycobacterium tuberculosis H37Rv strain using the BACTEC 460 radiometric system. A 3D-QSAR study based on CoMFA and CoMSIA was performed on these pyrazole derivatives to correlate their chemical structures with the observed activity against M. tuberculosis. The CoMFA model provided a significant correlation of steric and electrostatic fields with the biological activity while the CoMSIA model could additionally shed light on the role of hydrogen bonding and hydrophobic features. The important features identified in the 3D-QSAR models have been used to propose new molecules whose activities are predicted higher than the existing systems. This study provides valuable directions to our ongoing endeavor of rationally designing more potent antitubercular agents. (C) 2011 Elsevier Ltd. All rights reserved.