1-acetyl-3-(4-bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-(1H)-pyrazole | 353268-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-acetyl-3-(4-bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-(1H)-pyrazole
• 英文别名: 1-acetyl-3-(4-bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro(1H)pyrazole；1-[5-(4-Bromophenyl)-3-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 353268-48-1
• 化学式: C₁₈H₁₇BrN₂O₂
• 分子量: 373.249
• InChiKey: NBLGDQOVNUSYKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-(4-溴苯基)-3-(4-甲氧基苯基)丙-2-烯-1-酮 、 溶剂黄146 在 一水合肼 作用下， 反应 12.0h， 生成 1-acetyl-3-(4-bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-(1H)-pyrazole
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of pyrazole derivatives as potential FabH inhibitors

  摘要：

  Fatty acid biosynthesis is essential for bacterial survival. FabH, beta-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and - \negative bacteria. Fifty-six 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 1-(5-(4-fluorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl) ethanone (12) and 1-(5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl) ethanone (13) were potent inhibitors of E. coli FabH. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.105

文献信息

• Design, synthesis, and structure–activity relationships of pyrazole derivatives as potential FabH inhibitors
  作者：Peng-Cheng Lv、Juan Sun、Yin Luo、Ying Yang、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2010.05.105

  日期：2010.8

  Fatty acid biosynthesis is essential for bacterial survival. FabH, beta-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and - \negative bacteria. Fifty-six 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 1-(5-(4-fluorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl) ethanone (12) and 1-(5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl) ethanone (13) were potent inhibitors of E. coli FabH. (C) 2010 Elsevier Ltd. All rights reserved.
• Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones
  作者：Kunal Nepali、Kanika Kadian、Ritu Ojha、Rajni Dhiman、Atul Garg、Gagandip Singh、Abhishek Buddhiraja、Preet Mohinder Singh Bedi、Kanaya Lal Dhar

  DOI：10.1007/s00044-011-9824-9

  日期：2012.10

  Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C-6-C-3-C-6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines.All the synthesized compounds were evaluated for in vitro cytotoxicity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Compound 68 was found to be the most potent showing broad spectrum of cytotoxicity against all the cell lines .