5-p-chlorophenoxy-3-methyl-1-phenylpyrazole-4-carbaldehyde | 909250-33-5

• 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-p-chlorophenoxy-3-methyl-1-phenylpyrazole-4-carbaldehyde
• 英文别名: 3-methyl-5-(4-chlorophenoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde；5-(4-chlorophenoxy)-3-methyl-1-phenylpyrazole-4-carbaldehyde
• CAS: 909250-33-5
• 化学式: C₁₇H₁₃ClN₂O₂
• 分子量: 312.755
• InChiKey: WXVJXXAQKLGHTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 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-p-chlorophenoxy-3-methyl-1-phenylpyrazole-4-carbaldehyde 在 sodium hydroxide 、 羟胺 作用下， 以 甲醇 为溶剂， 生成 5-(4-Chloro-phenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde oxime
  参考文献：
  名称：

  Identification of antitumor activity of pyrazole oxime ethers

  摘要：

  A series of pyrazole oxime ether derivatives were prepared and examined as cytotoxic agents. In particular, 5-phenoxypyrazole was comparable to doxorubicin, while exhibiting very potent cytotoxicity against XF 498 and HCT15. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.082
• 作为产物：
  描述：

  3-甲基-1-苯基-1H-吡唑-5-醇 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5-p-chlorophenoxy-3-methyl-1-phenylpyrazole-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

• 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。
• 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, 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。
• 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, computational and biological study of pyrazole derivatives
  作者：N. Manju、Balakrishna Kalluraya、Asma、Madan S. Kumar

  DOI：10.1016/j.molstruc.2019.05.049

  日期：2019.10

  In the present study, the spectroscopic characterization of novel pyrazoline scaffold was studied. Title compounds were synthesized by microwave and conventional heating method and are characterized by FT-IR, 1H NMR, 13C NMR and analytical data. The single crystal X-ray diffraction method was used to determine the three-dimensional structures of the compounds 4a and 4c. From the X-ray analysis, it was

  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 =