1-(2-hydroxyphenyl)-3-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-propenone | 1262386-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-hydroxyphenyl)-3-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-propenone
• 英文别名: 3-(5-chloro-3-methyl-1-phenylpyrazol-4-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 1262386-41-3
• 化学式: C₁₉H₁₅ClN₂O₂
• 分子量: 338.793
• InChiKey: MJAHXHLVDUSDHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55.12
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)-3-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-propenone 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以83 %的产率得到2-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  A Divergent Synthesis and in vitro Biological Evaluation of Novel Pyrazolyl Chalcones and Pyrazolyl Flavones

  摘要：

  A total of sixteen flavonoids, eight each of pyrazolyl chalcones [IM-3(a-h)] and pyrazolyl flavones [IM-4(a-h)] were synthesized and tested for in vitro antidiabetic, antiarthritic, anticoagulant, anthelmintic, anti-inflammatory and antioxidant activities by various methods such as α-amylase inhibitory method, egg albumin denaturation method, prothrombin time method, paralysis and death time method, bovine serum denaturation method and DPPH radical scavenging activity method, respectively. Structural analysis of the synthesized chalcone and flavone derivatives was carried out by various characterization techniques such as IR, 1H NMR, 13C NMR, LC-MS and elemental analysis. Out of all the synthesized derivatives IM-3a containing dibenzyloxy groups had displayed the most promising activity in all the in vitro analysis with IC50 value ranging from 59.33 ± 10.26-144.44 ± 11.16 µg/mL. Compound IM-3a may prove to be a potential therapeutic option owing to its strong antidiabetic, antiarthritic, anticoagulant, anthelmintic, anti-inflammatory and and antioxidant properties.

  DOI：

  10.14233/ajchem.2024.31722
• 作为产物：
  描述：

  依达拉奉 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 1-(2-hydroxyphenyl)-3-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-propenone
  参考文献：
  名称：

  Synthesis of 4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(substituted phenyl)pyrimidin-2-ol Analogues as Anti-Inflammatory and Analgesic Agents

  摘要：

  合成了一系列16个新型4-(5-氯-3-甲基-1-苯基-1H-吡唑-4-基)-6-(取代苯基)嘧啶-2-醇类似物，在进行毒性预测和药物评分研究后，产率令人满意。随后对10个化合物进行了抗炎、镇痛、溃疡生成和脂质过氧化活性测试，采用已知的报告方法。发现4-(5-氯-3-甲基-1-苯基-1H-吡唑-4-基)-6-(4-氯苯基)嘧啶-2-醇（6g）是该系列中的一种有效化合物，显示出良好的抗炎（81.91 ± 7.69% 抑制）和镇痛活性（53.25 ± 2.91），且溃疡生成效应较小（0.66 ± 0.40）。

  DOI：

  10.2174/15701808113100890022

文献信息

• Design, synthesis, and characterization of some novel pyrazolo [1,5-a] pyrimidines as potent antimicrobial agents
  作者：Bhaskar S. Dawane、Shankaraiah G. Konda、Sainath B. Zangade

  DOI：10.1002/jhet.413

  日期：——

  A novel series of pyrazolo [1,5‐a] pyrimidines were synthesized by the condensation of substituted chalcones with 5‐amino pyrazole in presence of dimethyl formamide. All the synthesized products were characterized by the spectral analysis. Further, all newly synthesized compounds were screened for their antimicrobial activity. Most of the compounds showed potent activity. J. Heterocyclic Chem., (2010)

  在二甲基甲酰胺存在下，取代的查耳酮与5-氨基吡唑缩合，合成了一系列新型的吡唑并[1,5-a]嘧啶。通过光谱分析对所有合成产物进行表征。此外，筛选所有新合成的化合物的抗微生物活性。大多数化合物显示出有效的活性。J.杂环化​​学。（2010）。
• A Facile Greener Assisted Protocol for the Synthesis of Some New 4-aryl-(5-chloro-3-Methyl-1-phenyl-1H-Pyrazol-4-yl)-4,5-dihydroisoxazol-3-yl) Derivatives and their in vitro Antimicrobial Activity
  作者：Baseer M. Shaikh、Shankaraiah G. Konda、Omprakash S. Yemul、Bhaskar S. Dawane

  DOI：10.5012/jkcs.2012.56.2.246

  日期：2012.4.20

  An efficient access, single step and environmentally benign synthesis of a new series of pyrazole containing isoxazolines derivatives were prepared by the condensation of chalcones bearing pyrazole moiety with hydroxyl amine hydrochloride in basic condition by using polyethylene glycol-400 (PEG) as a greener reaction solvent. The advantages of the present methodology are mild reaction condition and avoidance of volatile organic solvent. Furthermore, these newly synthesized compounds were screened for their antimicrobial activity against various pathogens like Escherichia coli (MTCC 2939), Salmonella typhi (MTCC 98), Staphylococcus aureus (MTCC 96), Bacillus subtilis (MTCC 441), Aspergillus niger (MTCC 281), Aspergillus flavus (MTCC 2501), Penicillium chrsogenum (MTCC 160) and Fusarium moniliformae (MTCC 156). Especially compound containing the hydroxyl group in C2-position and presence of halo (I, Br and Cl) groups as substituents at $C_3$ and $C_5$ position on the benzene nucleus showed the higher activity. Furthermore, compounds bearing methyl groups in combination with I and Br which enhanced the activity.

  使用聚乙二醇-400（PEG）作为更环保的反应溶剂，在碱性条件下通过含吡唑分子的查耳酮与羟胺盐酸盐的缩合，制备了一系列新的含吡唑的异噁唑啉衍生物，这是一种高效、单步和环保的合成方法。本方法的优点是反应条件温和，避免使用挥发性有机溶剂。此外，还对这些新合成的化合物进行了筛选，以检测它们对各种病原体的抗菌活性，如大肠埃希氏菌（MTCC 2939）、伤寒沙门氏菌（MTCC 98）、金黄色葡萄球菌（MTCC 2939）、金黄色葡萄球菌（MTCC 98）、金黄色葡萄球菌（MTCC 96）、枯草芽孢杆菌（MTCC 441）、黑曲霉（MTCC 281）、黄曲霉（MTCC 2501）、青霉（MTCC 160）和镰刀菌（MTCC 156）。尤其是 C2 位含有羟基，苯核 $C_3$ 和 $C_5$ 位含有卤代（I、Br 和 Cl）基团的化合物显示出更高的活性。此外，含有甲基和 I、Br 的化合物也提高了活性。