5-(4-fluorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde | 926257-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-fluorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 5-(4-fluorophenoxy)-3-methyl-1-phenylpyrazole-4-carbaldehyde
• CAS: 926257-97-8
• 化学式: C₁₇H₁₃FN₂O₂
• mdl: MFCD03950729
• 分子量: 296.301
• InChiKey: XNKFNEYDDWWPOK-UHFFFAOYSA-N

物化性质

• 沸点：
  419.1±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.058
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-fluorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 在 叔丁基过氧化氢 、 1,3-dibutyl-1H-benzo[d]-[1,2,3]triazol-3-ium bromide 作用下， 以 水 为溶剂， 反应 24.0h， 以67%的产率得到6-fluoro-3-methyl-1-phenylchromeno[2,3-c]pyrazol-4(1H)-one
  参考文献：
  名称：

  Green Method for the Synthesis of Chromeno[2,3-c]pyrazol-4(1H)-ones through Ionic Liquid Promoted Directed Annulation of 5-(Aryloxy)-1H-pyrazole-4-carbaldehydes in Aqueous Media

  摘要：

  The first classical heterocyclic ionic liquid (IL) promoted C-H bond oxidant cross-doupling,reaction for the intramolecular annulation of 5-(aryloxy)-1H-pyrazole-4-carbal- dehydes to chromeno[2,37c]pyrazol-4(1H)-ones has been disclosed The promoter 1,3-dibutyl-1H-benzo[d]fl 2 3]- triazol-34-ium bromide can be easily recycled reused with the same efficacies for at least five cycles in aqueous medium The strategy works smoothly and provides applicable protocol to construct a Wide range of products.

  DOI：

  10.1021/acs.orglett.5b00033
• 作为产物：
  描述：

  3-(Phenylhydrazinylidene)butanoic acid 在 potassium carbonate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-fluorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-aryloxypyrazole derivatives bearing a rhodanine-3-aromatic acid as potential antimicrobial agents

  摘要：

  Three novel series of 5-aryloxypyrazole derivatives have been synthesized and tested for their antibacterial activity. The majority of the synthesized compounds showed potent inhibitory activity against Gram-positive bacteria Staphylococcus aureus 4220, especially against the strains of multidrug-resistant clinical isolates (MRSA3167/3506 and QRSA3505/3519). Among which compounds IIIb, IIIg and IIIm showed the most potent levels of activity (MIC = 1 mu g/mL) against the multidrug-resistant strains. And cytotoxic activity assay showed that the compounds tested did not affect cell viability on the Human cervical (HeLa) cells at their MICs. The current study therefore suggests that 5-aryloxypyrazoles bearing a rhodanine-3-aromatic acid moiety are promising scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.107

文献信息

• Design, synthesis and evaluation of dihydrotriazine derivatives-bearing 5-aryloxypyrazole moieties as antibacterial agents
  作者：Tian-Yi Zhang、Chun-Shi Li、Ming-Yue Cui、Xue-Qian Bai、Jiang-Hui Chen、Ze-Wen Song、Bo Feng、Xue-Kun Liu

  DOI：10.1007/s11030-020-10071-9

  日期：2021.5

  study implied that compound 10d exerted its antibacterial activity through DHFR inhibition. Moreover, significant inhibition of biofilm formation was observed in bacterial cells treated with MIC conc. of 10d as visualized by SEM micrographs. Graphic abstract Twenty-nine target compounds were designed, synthesized and evaluated in terms of their antibacterial and antifungal activities.

  摘要 在本研究中，合成了一系列带有 5-芳氧基吡唑部分的二氢三嗪衍生物，并通过不同的光谱工具确认了它们的结构。体外生物学评价表明，与参比药物相比，部分目标化合物具有良好的抗菌和抗真菌活性。在这些新型杂交体中，化合物10d显示出最有效的活性，对金黄色葡萄球菌4220、MRSA 3506 和大肠杆菌1924 菌株的最小抑制浓度值 (MIC) 为 0.5 µg/mL 。化合物6d , 6m , 10d和10g的细胞毒活性在 MCF-7 和 HeLa 细胞中进行评估。生长动力学研究表明，当用不同浓度处理时，可显着抑制细菌生长。的10D。体外酶研究表明化合物10d通过抑制DHFR发挥抗菌活性。此外，在用 MIC conc 处理的细菌细胞中观察到生物膜形成的显着抑制。的10D的SEM照片的可视化。 图形摘要 设计、合成了 29 种目标化合物，并评估了它们的抗菌和抗真菌活性。
• Synthesis and Evaluation on Anticonvulsant Activities of Pyrazolyl Semicarbazones
  作者：Xian-Qing Deng、Ming-Xia Song、Hai-Hong Yu

  DOI：10.14233/ajchem.2014.18218

  日期：——

  In this paper, a series of 2-[(5-phenoxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-methylene]hydrazine carboxamides were synthesized and evaluated for their anticonvulsant activities using the maximal electroshock method. Their neurotoxicities were determined applying the rotarod test. Interestingly, all compounds showed anticonvulsant activity with long duration of protection effects in the maximal electroshock test. Among which, compound 5m was found to have promising anticonvulsant activity, which gave an ED50 of 42.4 mg/kg and a protective index value of 3.7, possessing better anticonvulsant activity and higher safety than marketed drugs valproate, but weaker than phenobarbital. Furthermore, the antagonistic activity against seizures induced by pentylenetetrazole of the compound 5m was also established, which suggested that compound 5m may exert anticonvulsant activity through g-aminobutyric acid (GABA)-mediated mechanisms.

  本文中，我们合成了一系列2-[(5-苯氧基-3-甲基-1-苯基-1H-吡唑-4-基)-亚甲基]酰肼羧酰胺，并利用最大电休克法评估了它们的抗惊厥活性。通过旋转棒试验测定了它们的中枢神经毒性。有趣的是，所有化合物在最大电休克试验中均显示出抗惊厥活性，且保护效果持久。其中，化合物5m表现出有前景的抗惊厥活性，其ED50为42.4 mg/kg，保护指数值为3.7，抗惊厥活性优于市场药物丙戊酸，但弱于苯巴比妥，并且安全性更高。此外，化合物5m对戊四氮诱导的惊厥也有拮抗活性，这表明化合物5m可能通过γ-氨基丁酸（GABA）介导的机制发挥抗惊厥作用。
• Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives: assessment of their antimicrobial, antituberculosis and antioxidant activity
  作者：Chetan B. Sangani、Jigar A. Makwana、Yong-Tao Duan、Nilesh J. Thumar、Meng-Yue Zhao、Yogesh S. Patel、Hai-Liang Zhu

  DOI：10.1007/s11164-015-2138-7

  日期：2016.3

  A new series of pyrazolo[1,2-b]phthalazine derivatives (4a–p) bearing the 5-aryloxypyrazole nucleus was synthesized by one-pot, three-component, base-catalyzed cyclo condensation reaction of 3-methyl-5-aryloxy-1-aryl-1H-pyrazole-4-carbaldehyde (1a–d), malononitrile or ethyl cyanoacetate (2a–b) and 2,3-dihydro-1,4-phthalazinedione (3a–b) in ethanol containing an eco friendly base, NaOH, in good to excellent yields. All synthesized compounds (4a–p) were duly characterized by physico-chemical parameters, 1H NMR, 13C NMR, FT-IR and LCMS techniques. In vitro antimicrobial activity of the synthesized compounds was investigated against a representative panel of pathogenic strains. Compounds 4e, 4g, 4h, 4k and 4o exhibited excellent antimicrobial activity compared with first line drugs. In vitro antituberculosis activity was evaluated against Mycobacterium tuberculosis H37Rv, and compounds 4g and 4o emerged as the promising antimicrobial members with better antituberculosis activity. A brine shrimp bioassay was carried out to study the in vitro cytotoxic properties of the synthesized compounds. In vitro antioxidant activity was evaluated by the ferric-reducing antioxidant power method. Compounds 4c, 4d, 4g and 4h showed the highest antioxidant potencies.

  通过一步法、三组分、碱催化的环缩合反应，以3-甲基-5-芳氧基-1-芳基-1H-吡唑-4-甲醛（1a–d）、丙二腈或氰乙酸乙酯（2a–b）和2,3-二氢-1,4-酞嗪二酮（3a–b）为原料，在含环保碱NaOH的乙醇中合成了含5-芳氧基吡唑核的一系列新型吡唑并[1,2-b]酞嗪衍生物（4a–p），产率良好至优秀。所有合成的化合物（4a–p）均通过物理化学参数、1H NMR、13C NMR、FT-IR和LCMS技术进行了适当表征。对合成的化合物进行了体外抗菌活性测试，针对一组有代表性的病原菌株进行了研究。与一线药物相比，化合物4e、4g、4h、4k和4o表现出优异的抗菌活性。体外抗结核活性针对结核分枝杆菌H37Rv进行了评估，化合物4g和4o作为有前景的抗菌成员，显示出更好的抗结核活性。通过盐水虾生物测定法研究了合成化合物的体外细胞毒性。通过铁还原抗氧化能力法评估了体外抗氧化活性。化合物4c、4d、4g和4h表现出最高的抗氧化活性。
• Synthesis and Herbicidal Activity of α-Amino Phosphonate Derivatives Containing Thiazole and Pyrazole Moieties
  作者：Zhi-Hua Yu、De-Qing Shi

  DOI：10.1080/10426500903251373

  日期：2010.7.30

  A series of novel α-amino phosphonate derivatives containing the thiazole and pyrazole moieties 3 were synthesized by the Mannich-type reaction of substituted pyrazole-aldehyde 1, 2-amino-5-ethoxycarbonyl-4-methyl-thiazole 2, and dialkyl phosphites or triphenyl phosphite in the presence of a Lewis acid such as magnesium perchlorate as the catalyst under solvent-free conditions. Their structures were

  通过取代吡唑醛 1、2-氨基-5-乙氧羰基-4-甲基-噻唑 2 和亚磷酸二烷基酯的曼尼希型反应合成了一系列含有噻唑和吡唑部分 3 的新型 α-氨基膦酸酯衍生物。在无溶剂条件下，在路易斯酸（如高氯酸镁）作为催化剂存在下，亚磷酸三苯酯。它们的结构通过光谱数据（IR、1H NMR、31P NMR、MS）和元素分析得到了明确证实。初步生物测定（体外）的结果表明，某些标题化合物 3 在 100 mg/L 时对双子叶植物（Brassica campestris L）或单子叶植物（Echinochloa crus-galli）具有中等除草活性。补充材料可用于本文。去出版商'
• Design, synthesis, and antibacterial evaluation of new Schiff’s base derivatives bearing nitroimidazole and pyrazole nuclei as potent E. coli FabH inhibitors
  作者：Chetan B. Sangani、Jigar A. Makwana、Yong-Tao Duan、Umesh P. Tarpada、Yogesh S. Patel、Ketan B. Patel、Vivek N. Dave、Hai-Liang Zhu

  DOI：10.1007/s11164-015-2018-1

  日期：2015.12

  New Schiff’s base derivatives 5a – j have been synthesized by reaction between 5-aryloxypyrazole-4-carbaldehydes 3a – j and 2-(2-methyl-5-nitro-1 H -imidazol-1- yl )acetohydrazide 4 in the presence of nickel (II) nitrate as a catalyst in ethanol at room temperature with good yield (75–88 %). All compounds were tested for antibacterial properties and inhibition of E. coli FabH. Of the compounds studied

  新的席夫碱衍生物 5a – j 是在以下条件下通过5-芳氧基吡唑-4-甲醛 3a – j 与2-（2-甲基-5-硝基-1 H- 咪唑-1- 基 ）乙酰肼 4 的反应合成 的在室温下，硝酸镍（II）作为乙醇催化剂的产率高（75-88％）。测试所有化合物的抗菌特性和对 大肠杆菌 FabH的抑制作用。在研究的化合物中，大多数化合物显示出有效的抗菌性能并抑制了 大肠杆菌 FabH活性。化合物 5i  通过以最小的结合能（ ΔG b  = -54.2961 kcal / mol）结合到 大肠杆菌 FabH受体 的活性位点，显示出最有效的抑制作用（IC 50 = 4.6±0.2 µM ）。结合通过两个氢键，两个π-π和三个π-阳离子相互作用得以稳定。