5-(2-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde | 1015870-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 5-(2-Methoxyphenoxy)-3-methyl-1-phenylpyrazole-4-carbaldehyde
• CAS: 1015870-44-6
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: LXGWYTSXMCWOOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 、 (2S)-3-methyl-2-(4-oxo-2-thioxothiazolidin-3-yl)pentanoic acid 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (2S)-2-[(5Z)-5-[[5-(2-methoxyphenoxy)-3-methyl-1-phenylpyrazol-4-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methylpentanoic acid
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of rhodanine-based 5-aryloxy pyrazoles against selected methicillin resistant and quinolone-resistant Staphylococcus aureus (MRSA and QRSA)

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2012.12.007
• 作为产物：
  描述：

  苯肼 在 盐酸 、 potassium carbonate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5-(2-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  含有 5-芳氧基吡唑部分的绕丹宁衍生物作为抗炎和抗癌剂

  摘要：

  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。

  DOI：

  10.1002/cbdv.202301844

文献信息

• 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。
• <p>Synthesis and Biological Evaluations of Monocarbonyl Curcumin Inspired Pyrazole Analogues as Potential Anti-Colon Cancer Agent</p>
  作者：Zhenli Min、Yue Zhu、Xing Hong、Zhijun Yu、Min Ye、Qiong Yuan、Xiamin Hu

  DOI：10.2147/dddt.s244865

  日期：——

  activity. Pyrazole is a five-membered aromatic heterocyclic system with various bioactivities incorporated frequently in drugs. However, few of MCACs inspired pyrazole analogues were investigated. To search for more potent cytotoxic agents based on MCACs, a series of new 1,5-diaryl/heteroaryl-1,4-pentadien-3-ones inspired pyrazole moiety was synthesized and evaluated on their anti-colon cancer activities

  目的：姜黄素的单羰基类似物 (MCACs) 因其具有良好的抗肿瘤活性而被广泛研究。吡唑是一种五元芳香杂环系统，具有多种生物活性，经常被纳入药物中。然而，很少有人研究了受MCACs启发的吡唑类似物。为了寻找基于 MCAC 的更有效的细胞毒剂，合成了一系列新的 1,5-二芳基/杂芳基-1,4-戊二烯-3-酮类化合物，并对其抗结肠癌活性进行了评估。 方法：合成了 15 种新化合物并通过光谱数据对其进行了表征，然后通过 MTT 法初步测试了它们对一组四种人类癌细胞系的细胞毒活性，即胃 (SGC-7901)、肝 (HepG2)、肺 ( A549) 和结肠 (SW620) 癌细胞。在这15种化合物中，化合物7h对SW620细胞表现出优异的选择性和显着的抗增殖活性。此外，通过transwell迁移和侵袭试验、克隆形成试验、细胞凋亡分析、细胞周期分析、Western印迹分析研究了这些机制。 结果：7h对SW620细胞的IC
• 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。
• 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.