3-Methyl-1-phenyl-5-[3-(trifluoromethyl)phenoxy]pyrazole-4-carbaldehyde | 1415020-45-9

• 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-Methyl-1-phenyl-5-[3-(trifluoromethyl)phenoxy]pyrazole-4-carbaldehyde
• 英文别名: 3-methyl-1-phenyl-5-[3-(trifluoromethyl)phenoxy]pyrazole-4-carbaldehyde
• CAS: 1415020-45-9
• 化学式: C₁₈H₁₃F₃N₂O₂
• 分子量: 346.309
• InChiKey: SWCYTKGXKBPEID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Methyl-1-phenyl-5-[3-(trifluoromethyl)phenoxy]pyrazole-4-carbaldehyde 在 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5'-(4-fluorophenoxy)-2,5-bis(4-fluorophenyl)-3'-methyl-1'-phenyl-3,4-dihydro-1'H,2H-3,4'-bipyrazole
  参考文献：
  名称：

  Design, synthesis and characterization of fluoro substituted novel pyrazolylpyrazolines scaffold and their pharmacological screening

  摘要：

  A novel series of fluoro substituted pyrazolylpyrazolines 7a-l was synthesized in good to excellent yield (77-88%) from pyrazole chalcones 5a-d and substituted phenyl hydrazine hydrochlorides 6a-c under microwave irradiation. The newly synthesized compounds were screened for their preliminary in vitro antibacterial activity against a panel of pathogenic stains of bacteria and fungi, antituberculosis activity against Mycobacterium tuberculosis H37Rv and antimalarial activity against Plasmodium falciparum. Compounds 7a, 7b, 7g, 7h, 7j and 7k displayed excellent activity against P. falciparum stain as compared to quinine IC50 0.268. Good antitubercular activity was exhibited by compounds 7a, 7e, 7h and 7k. Some of them also exhibited superior antibacterial activity as compared to the first line drugs.

  DOI：

  10.1016/j.ejmech.2014.07.008
• 作为产物：
  描述：

  ethyl 3-(2-phenylhydrazono)butanoate 在 盐酸 、 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 3-Methyl-1-phenyl-5-[3-(trifluoromethyl)phenoxy]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。
• Green synthesis and pharmacological screening of polyhydroquinoline derivatives bearing a fluorinated 5-aryloxypyrazole nucleus
  作者：Sharad C. Karad、Vishal B. Purohit、Dipak K. Raval、Piyush N. Kalaria、Jemin R. Avalani、Parth Thakor、Vasudev R. Thakkar

  DOI：10.1039/c5ra00388a

  日期：——

  Green synthesis, biological evaluation and SAR study of polyhydroquinoline scaffold bearing fluorinated 5-aryloxypyrazole nucleus is discussed.

  绿色合成，生物评价和带有氟化5-芳氧吡唑核的多羟基喹啉骨架的结构活性关系研究。
• 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.
• Dihydrotriazine derivatives display high anticancer activity and inducing apoptosis, ROS, and autophagy
  作者：Tian-Yi Zhang、Xue-Qian Bai、Zhi-Jiang Zhou、Lian-Hai Jin、Dong-Hai Zhao、Si-Mei Sun

  DOI：10.1016/j.bioorg.2022.105813

  日期：2022.7