3-(4-chlorophenyl)-1-(2-fluorophenyl)prop-2-en-1-one | 1221963-20-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4-chlorophenyl)-1-(2-fluorophenyl)prop-2-en-1-one
• 英文别名: 3-(4-Chlorophenyl)-1-(2-fluorophenyl)prop-2-en-1-one
• CAS: 1221963-20-7
• 化学式: C₁₅H₁₀ClFO
• 分子量: 260.695
• InChiKey: OTYLGCMDVHXBEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-1-(2-fluorophenyl)prop-2-en-1-one 、 溶剂黄146 在 一水合肼 作用下， 反应 12.0h， 生成 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one
  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
• 作为产物：
  描述：

  2'-氟苯乙酮 、 4-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(4-chlorophenyl)-1-(2-fluorophenyl)prop-2-en-1-one
  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

• Copper triflate-mediated synthesis of 1,3,5-triarylpyrazoles in [bmim][PF6] ionic liquid and evaluation of their anticancer activities
  作者：V. Kameshwara Rao、Rakesh Tiwari、Bhupender S. Chhikara、Amir Nasrolahi Shirazi、Keykavous Parang、Anil Kumar

  DOI：10.1039/c3ra41830h

  日期：——

  A simple, efficient, and environment friendly protocol for the synthesis of 1,3,5-triarylpyrazole and 1,3,5-triarylpyrazolines in [bimm][PF6] ionic liquid mediated by Cu(OTf)2 is described. The reaction protocol gave 1,3,5-triarylpyrazoles in good to high yields (71-84%) via a one-pot addition-cyclocondensation between chalcones and arylhydrazines, and oxidative aromatization without requirement for

  描述了一种简单，有效且环保的方案，用于在由Cu（OTf）2介导的[bimm] [PF6]离子液体中合成1,3,5-三芳基吡唑和1,3,5-三芳基吡唑啉。该反应方案通过查耳酮与芳基肼之间的一锅加成-环缩合和氧化芳构化而获得了高至高产率（71-84％）的1,3,5-三芳基吡唑，而无需额外的氧化剂。催化剂可以重复使用多达四个循环，而催化活性没有太大损失。评估吡唑（4a-o）和吡唑啉（3a-n​​）在SK-OV-3，HT-29和HeLa人癌细胞系中的抗增殖活性。在所有化合物中，浓度为50μM的3b抑制HeLa细胞的细胞增殖80％。
• 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.