3-(2-Fluorophenyl)-1-phenylpyrazole-4-carbaldehyde | 1152934-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-Fluorophenyl)-1-phenylpyrazole-4-carbaldehyde
• CAS: 1152934-95-6
• 化学式: C₁₆H₁₁FN₂O
• 分子量: 266.275
• InChiKey: OPCDRZOUJCZCQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  34.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羧甲基绕丹宁 、 3-(2-Fluorophenyl)-1-phenylpyrazole-4-carbaldehyde 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以90%的产率得到(Z)-2-(5-((3-(2-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid
  参考文献：
  名称：

  含有若丹宁-3-脂肪酸部分作为潜在抗菌剂的新型1,3-二芳基吡唑衍生物的合成

  摘要：

  在本研究中，合成了一系列带有若丹宁-3-脂肪酸部分的1,3-二芳基吡唑衍生物，并测试了它们对各种革兰氏阳性和革兰氏阴性细菌的抗菌活性。按照维尔斯迈尔-哈克（Vilsmeier-Haack）策略，合成了1,3-二芳基-4-甲酰基吡唑类化合物作为关键中间体。MIC为2μg/ mL的几种化合物显示出比对照更强的耐甲氧西林金黄色葡萄球菌（MRSA）的抗菌活性。这些化合物均未显示出对革兰氏阴性细菌的任何活性。

  DOI：

  10.1016/j.ejmech.2011.12.011
• 作为产物：
  描述：

  2'-氟苯乙酮 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 3-(2-Fluorophenyl)-1-phenylpyrazole-4-carbaldehyde
  参考文献：
  名称：

  吡唑-咪唑并[1,2-α]吡啶分子缀合物的新文库：合成，抗菌活性和分子对接研究。

  摘要：

  设计并通过一锅三组分串联反应合成了新型吡唑-咪唑并[1,2-α]吡啶骨架。通过光谱技术（NMR，IR和HRMS）证实了合成的缀合物的结构。对耐甲氧西林金黄色葡萄球菌和大肠杆菌，鼠伤寒沙门氏菌，肺炎克雷伯菌和铜绿假单胞菌等正常菌株的十二种合成分子（7a，8a-k）的体外抗菌评估建立了有效的抗菌剂8b，8d，8e，8h和8i。与标准药物环丙沙星相比，具有最低最低杀菌浓度的杀菌剂。

  DOI：

  10.1111/cbdd.13632

文献信息

• Discovery of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups as potential PTP1B inhibitors
  作者：Liangpeng Sun、Peipei Wang、Lili Xu、Lixin Gao、Jia Li、Huri Piao

  DOI：10.1016/j.bmcl.2019.03.023

  日期：2019.5

  Two series of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, IIIv was found to have the best in vitro inhibition activity against PTP1B (IC50 = 0.67 ± 0.09 µM) and the best selectivity (9-fold) between PTP1B and T-cell protein tyrosine phosphatase (TCPTP)

  含有若丹宁-3-链烷酸基团的两个系列的1,3-二苯基-1H-吡唑衍生物被确定为竞争性蛋白酪氨酸磷酸酶1B（PTP1B）抑制剂。在研究的化合物中，发现IIIv对PTP1B具有最佳的体外抑制活性（IC50 = 0.67±0.09 µM），并且在PTP1B和T细胞蛋白酪氨酸磷酸酶（TCPTP）之间具有最佳选择性（9倍）。分子对接研究表明，化合物IIIm，IIIv和IVg可同时在催化位点和相邻的pTyr结合位点占据。这些结果为设计PTP1B和其他PTP抑制剂提供了新的先导化合物。
• Synthesis and biological evaluation of 1,3-diaryl pyrazole derivatives as potential antibacterial and anti-inflammatory agents
  作者：Ya-Ru Li、Chao Li、Jia-Chun Liu、Meng Guo、Tian-Yi Zhang、Liang-Peng Sun、Chang-Ji Zheng、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2015.10.028

  日期：2015.11

  Three series of 1,3-diaryl pyrazole derivatives bearing aminoguanidine or furan-2-carbohydrazide moieties have been synthesized, characterized and evaluated for antibacterial and anti-inflammatory activities. Most of the synthesized compounds showed potent inhibition of several Gram-positive bacterial strains (including multidrug-resistant clinical isolates) and Gram-negative bacterial strains with minimum inhibitory concentration values in the range of 1-64 mu g/mL. Compounds 6g, 6l and 7l presented the most potent inhibitory activity against Gram-positive bacteria (e.g. Staphylococcus aureus 4220), Gram-negative bacteria (e.g. Escherichia coli 1924) and the fungus, Candida albicans 7535, with minimum inhibitory concentration values of 1 or 2 mu g/mL. Compared with previous studies, these compounds exhibited a broad spectrum of inhibitory activity. Furthermore, compound 7l showed the greatest anti-inflammatory activity (93.59% inhibition, 30 min after intraperitoneal administration), which was more potent than the reference drugs ibuprofen and indomethacin. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and antibacterial activity of novel 1,3-diphenyl-1H-pyrazoles functionalized with phenylalanine-derived rhodanines
  作者：Chang-Ji Zheng、Li-Li Xu、Liang-Peng Sun、Jing Miao、Hu-Ri Piao

  DOI：10.1016/j.ejmech.2012.10.012

  日期：2012.12

  In the present study, a series of novel 1,3-diphenyl-1H-pyrazoles functionalized with phenylalanine-derived rhodanine derivatives were synthesized and evaluated for their antibacterial activity. Compounds 4, 6, 9, 10, 12 and 15 exhibited stronger activity than the standard drugs, norfloxacin and oxacillin, with MIC values of 1 mu g/mL against methicillin-resistant Staphylococcus aureus and quinolone-resistant S. aureus. None of the compounds showed any activity against Gram-negative bacteria. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis of novel 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties as potential antibacterial agents
  作者：Li-Li Xu、Chang-Ji Zheng、Liang-Peng Sun、Jing Miao、Hu-Ri Piao

  DOI：10.1016/j.ejmech.2011.12.011

  日期：2012.2

  In the present study, a series of 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties were synthesized and their antimicrobial activities were tested against various Gram-positive and Gram-negative bacteria. 1,3-diaryl-4-formylpyrazoles were synthesized as key intermediates following a Vilsmeier–Haack strategy. Several compounds with an MIC of 2 μg/mL, exhibited stronger antibacterial

  在本研究中，合成了一系列带有若丹宁-3-脂肪酸部分的1,3-二芳基吡唑衍生物，并测试了它们对各种革兰氏阳性和革兰氏阴性细菌的抗菌活性。按照维尔斯迈尔-哈克（Vilsmeier-Haack）策略，合成了1,3-二芳基-4-甲酰基吡唑类化合物作为关键中间体。MIC为2μg/ mL的几种化合物显示出比对照更强的耐甲氧西林金黄色葡萄球菌（MRSA）的抗菌活性。这些化合物均未显示出对革兰氏阴性细菌的任何活性。
• New library of pyrazole–imidazo[1,2‐α]pyridine molecular conjugates: Synthesis, antibacterial activity and molecular docking studies
  作者：Oluwakemi Ebenezer、Paul Awolade、Neil Koorbanally、Parvesh Singh

  DOI：10.1111/cbdd.13632

  日期：2020.1

  A library of novel pyrazole-imidazo[1,2-α]pyridine scaffolds was designed and synthesized through a one-pot three-component tandem reaction. The structures of synthesized conjugates were confirmed by spectroscopic techniques (NMR, IR and HRMS). In vitro antibacterial evaluation of the twelve synthesized molecules (7a, 8a-k) against methicillin-resistant Staphylococcus aureus and normal strains of Escherichia

  设计并通过一锅三组分串联反应合成了新型吡唑-咪唑并[1,2-α]吡啶骨架。通过光谱技术（NMR，IR和HRMS）证实了合成的缀合物的结构。对耐甲氧西林金黄色葡萄球菌和大肠杆菌，鼠伤寒沙门氏菌，肺炎克雷伯菌和铜绿假单胞菌等正常菌株的十二种合成分子（7a，8a-k）的体外抗菌评估建立了有效的抗菌剂8b，8d，8e，8h和8i。与标准药物环丙沙星相比，具有最低最低杀菌浓度的杀菌剂。