5-(2,4-dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde | 1134201-84-5

• 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-(2,4-dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 5-(2,4-Dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde；5-(2,4-dichlorophenoxy)-3-methyl-1-phenylpyrazole-4-carbaldehyde
• CAS: 1134201-84-5
• 化学式: C₁₇H₁₂Cl₂N₂O₂
• 分子量: 347.2
• InChiKey: DBUYMODKGXPIFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2,4-dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 在 hydrazine hydrate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酸 为溶剂， 反应 4.12h， 生成 1-(5-(5-(2,4-dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-(furan-2-yl)-4,5-dihydropyrazol-1-yl)ethanone
  参考文献：
  名称：

  吡唑衍生物的合成、计算和生物学研究

  摘要：

  摘要 本研究对新型吡唑啉支架的光谱表征进行了研究。标题化合物通过微波和常规加热方法合成，并通过 FT-IR、1H NMR、13C NMR 和分析数据进行表征。使用单晶X射线衍射法测定化合物4a和4c的三维结构。从 X 射线分析中观察到，两种化合物 4a 和 4c 分别在具有 P-1 空间群的三斜晶系​​中结晶。化合物 4a 和 4c 结晶的细胞参数为 a = 10.3700 (7) A, b = 10.91607 (7) A, c = 12.7822 (7) A, α = 107.280 (5)o, β = 98.438 (5) o, γ = 116.105 (7) o, V = 1173.94 (17) A3, Z = 2 and a = 10.2990 (7) A, b = 10.9915 (8) A, c = 12.5985 (7) A, α = 104.725 (5)o , β =

  DOI：

  10.1016/j.molstruc.2019.05.049
• 作为产物：
  描述：

  依达拉奉 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(2,4-dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Synthesis and Evaluation on Anticonvulsant Activities of Pyrazolyl Semicarbazones

  摘要：

  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。

  DOI：

  10.14233/ajchem.2014.18218

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。
• Design and Synthesis of Pyrazolyl Thiosemicarbazones as New Anticonvulsants
  作者：Xian Qing Deng、Ming Xia Song

  DOI：10.5012/bkcs.2014.35.9.2733

  日期：2014.9.20

  A series of pyrazolyl thiosemicarbazone derivatives were synthesized and evaluated for their anticonvulsant activity using the maximal electroshock (MES) method. Interestingly, all compounds prepared showed long duration of protection effect in the MES screens. Among them, compound 5b was considered as the most promising one with an $ED_50}$ value of 47.3 mg/kg, and a PI value of 4.8, which was superior to phenobarbital and valproate in the aspect of safety. Furthermore, compound 5b showed protection against seizures induced by pentylenetetrazole suggesting that compound 5b may exert anticonvulsant activity through GABA-mediated mechanisms.

  一系列吡唑啉基硫代缩氨基脲衍生物被合成并采用最大电休克（MES）法评估了它们的抗惊厥活性。有趣的是，所有制备的化合物在MES筛选中均显示出长时间的保护效应。其中，化合物5b被认为是最有前景的，其ED50值为47.3 mg/kg，PI值为4.8，在安全性方面优于苯巴比妥和丙戊酸。此外，化合物5b对戊四唑诱发的惊厥也显示出保护作用，表明化合物5b可能通过GABA介导的机制发挥抗惊厥活性。
• Rhodanine Derivatives Containing 5‐Aryloxypyrazole Moiety as Anti‐inflammatory and Anticancer Agents
  作者：Lin Zhu、Chao Ye、Shuang Chen、Yuqi Fang、Yu Zhang、Tianyi Zhang

  DOI：10.1002/cbdv.202301844

  日期：2024.2

  In this study, a series of rhodanine derivatives containing 5-aryloxypyrazole moiety were identified as potential agents with anti-inflammatory and anticancer properties. Most of the synthesized compounds demonstrated anti-inflammatory and anticancer activity. Notably, compound 7 g (94.1 %) exhibited significant anti-inflammatory activity compared with the reference drugs celecoxib (52.5 %) and hydrocortisone

  在这项研究中，一系列含有5-芳氧基吡唑部分的绕丹宁衍生物被鉴定为具有抗炎和抗癌特性的潜在药物。大多数合成的化合物都表现出抗炎和抗癌活性。值得注意的是，与参考药物塞来昔布（52.5%）和氢化可的松（79.4%）相比，化合物7g （94.1%）表现出显着的抗炎活性。不同浓度的化合物7g以剂量依赖性方式有效抑制一氧化氮(NO)的产生。 Western blot结果显示，化合物7g可以阻止LPS诱导的巨噬细胞炎症介质的表达。酶联免疫吸附测定 (ELISA) 测定表明7 g是一种有前途的化合物，能够阻断 COX-2 的下游信号传导。总之，这些发现表明化合物7 g可能是进一步研究的有希望的候选者。
• Synthesis and antibacterial evaluation of rhodanine-based 5-aryloxy pyrazoles against selected methicillin resistant and quinolone-resistant Staphylococcus aureus (MRSA and QRSA)
  作者：Ming-Xia Song、Chang-Ji Zheng、Xian-Qing Deng、Liang-Peng Sun、Yan Wu、Lan Hong、Ying-Jing Li、Yi Liu、Zhi-Yu Wei、Ming-Jun Jin、Hu-Ri Piao

  DOI：10.1016/j.ejmech.2012.12.007

  日期：2013.2

  With an intention to synergize the anti-bacterial activity of 5-aryloxy pyrazole and rhodanine derivatives, eight series of hybrid compounds have been synthesized and evaluated for their antibacterial activity. The majority of the synthesized compounds showed good inhibitory activity against selected methicillin resistant and quinolone-resistant Staphylococcus aureus (MRSA, QRSA) with minimum inhibitory concentration (MIC) values in the range of 1-32 mu g/mL. The cytotoxicity test suggests that these compounds exhibited in vitro antibacterial activity at non-cytotoxic concentrations. These studies therefore suggest that rhodanine-based 5-aryloxy pyrazoles are interesting scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological evaluation of 5-aryloxypyrazole derivatives bearing a rhodanine-3-aromatic acid as potential antimicrobial agents
  作者：Chang-Ji Zheng、Ming-Xia Song、Liang-Peng Sun、Yan Wu、Lan Hong、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2012.09.107

  日期：2012.12

  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.