5-(2,6-Dichlorophenoxy)-3-methyl-1-phenylpyrazole-4-carbaldehyde | 1415020-43-7

• 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-(2,6-Dichlorophenoxy)-3-methyl-1-phenylpyrazole-4-carbaldehyde
• 英文别名: 5-(2,6-dichlorophenoxy)-3-methyl-1-phenylpyrazole-4-carbaldehyde
• CAS: 1415020-43-7
• 化学式: C₁₇H₁₂Cl₂N₂O₂
• 分子量: 347.2
• InChiKey: YICSHYRYLWASIX-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-(2,6-Dichlorophenoxy)-3-methyl-1-phenylpyrazole-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-(2,6-dichlorophenoxy)-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：

  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 5-(2,6-Dichlorophenoxy)-3-methyl-1-phenylpyrazole-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

• 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。
• 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, biological evaluation, and docking studies of pyrazole-linked benzothiazole hybrids as promising anti-TB agents
  作者：Reham A. Mohamed-Ezzat、Mohamed A. Omar、Ahmed Temirak、Ahmed S. Abdelsamie、Marwa M. Abdel-Aziz、Shadia A. Galal、Galal H. Elgemeie、Hoda I. El Diwani、Keith J. Flanagan、Mathias O Senge

  DOI：10.1016/j.molstruc.2024.138415

  日期：2024.9

  reference compound, triclosan, with IC values of 6.4–7.9 μM. Moreover, a molecular docking study was carried out to investigate the predicted binding interactions of the synthesized inhA inhibitors in the binding pocket of the inhA enzyme. The calculated docking energies of the developed novel pyrazole-linked benzothiazole hybrids were consistent with their tested anti-tubercular activity.

  结核病 (TB) 是一种全球流行病，每年夺去数百万人的生命。然而，耐药菌株使结核病的治疗变得相当具有挑战性。在此，合成了一系列新的吡唑连接的苯并噻唑杂化物，并评估了它们对三种菌株（药物敏感（DS）、多重耐药（MDR）和广泛耐药（XDR））的抗结核活性。取代的2,5-二甲基苯氧基-、2,6-二氯苯氧基-、2,6-二甲氧基苯氧基-、4-甲基哌嗪-1-基-和吡咯烷-1-基吡唑-苯并噻唑缀合物（分别为化合物和）显示出有前景的抗-与参考化合物异烟肼对 DS 菌株的结核活性进行比较（MIC：1.74–3.68 μM/mL）为了进一步研究这些抗结核化合物的作用模式，它们对烯酰基载体蛋白还原酶的抑制（ InhA）进行了测试。与参考化合物三氯生相比，3-乙酰氨基苯氧基-、2,6-二氯苯氧基-和吡咯烷-1-基吡唑-苯并噻唑缀合物（化合物 和 ）对 InhA 表现出强烈的抑制作用，IC 值为 6.4–7.9 μ
• 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.