3-甲基-5-苯氧基-1-苯基-1H-吡唑-4-甲醛 | 30241-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-甲基-5-苯氧基-1-苯基-1H-吡唑-4-甲醛
• 英文名称: 3-methyl-5-phenoxy-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-methyl-5-phenoxy-1-phenylpyrazole-4-carboxaldehyde；5-phenoxy-3-methyl-1-phenylpyrazole-4-carbaldehyde；1-phenyl-3-methyl-5-phenoxypyrazol-4-carboxaldehyde；1-phenyl-3-methyl-5-phenyloxyl-4-pyrazolocarbaldehyde；3-methyl-5-phenoxy-1-phenylpyrazole-4-carbaldehyde
• CAS: 30241-46-4
• 化学式: C₁₇H₁₄N₂O₂
• mdl: MFCD02711484
• 分子量: 278.31
• InChiKey: PPEYODGHGWCLLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 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：
  3

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  3-甲基-5-苯氧基-1-苯基-1H-吡唑-4-甲醛 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73%的产率得到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 3-甲基-5-苯氧基-1-苯基-1H-吡唑-4-甲醛
  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。
• 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。
• N-Heterocyclic Carbene-Catalyzed Aerobic Oxidative Direct Esterification of Aldehydes with Organoboronic Acids
  作者：Jing-Jing Meng、Min Gao、Yu-Ping Wei、Wen-Qin Zhang

  DOI：10.1002/asia.201200076

  日期：2012.5

  A simple procedure affording benzoates through a NHC‐catalyzed aerobic oxidative esterification of aldehydes with organoboronic acids has been disclosed. This process allows access to a wide variety of aromatic esters in good to excellent yields under simple, efficient, and sustainable reaction conditions (see scheme).

  公开了一种简单的方法，该方法通过NHC催化的醛与有机硼酸的好氧氧化酯化反应生成苯甲酸酯。该方法可以在简单，有效和可持续的反应条件下以良好的收率获得各种芳族酯（参见方案）。
• 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。