1-[5-(4-hydroxyphenyl)-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone | 313394-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-[5-(4-hydroxyphenyl)-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone
• 英文别名: 1-(5-(4-hydroxyphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)ethanone；1-acetyl-4,5-dihydro-3-methyl-5-(4-hydroxyphenyl)-1H-pyrazole；1-[3-(4-hydroxyphenyl)-5-methyl-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 313394-46-6
• 化学式: C₁₂H₁₄N₂O₂
• mdl: MFCD01543165
• 分子量: 218.255
• InChiKey: XEXDQDGLXRNLDA-UHFFFAOYSA-N

物化性质

• 熔点：
  210-211 °C(Solv: acetone (67-64-1))
• 沸点：
  382.4±52.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  烟酰氯 、 1-[5-(4-hydroxyphenyl)-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以60.1%的产率得到4-(1-acetyl-3-methyl-4,5-dihydro-1H-pyrazol-5-yl)phenyl nicotinate
  参考文献：
  名称：

  Synthesis, Structure, and Antibacterial Activity of Novel 5-Arylpyrazole Derivatives

  摘要：

  合成了一系列新型 1-(乙酰基、甲酰胺、硫代甲酰胺)取代-5-(取代苯基)-3-甲基-4,5-二氢吡唑衍生物，并通过 1H NMR、IR、ESI-MS 和元素分析对其进行了表征。化合物 6h 和 6q 通过单晶 X 射线结构分析得到了进一步表征。所有化合物都对枯草杆菌 ATCC 6633、大肠杆菌 ATCC 35218、荧光假单胞菌 ATCC 13525 和金黄色葡萄球菌 ATCC 6538 进行了体外抗菌潜力筛选。其中，化合物 5ac 和 6h 对枯草杆菌 ATCC 6633 的最小抑制浓度值为 1.562 μg mL-1，与阳性对照青霉素相当。根据实验数据还讨论了结构-效应关系。

  DOI：

  10.1071/ch07253
• 作为产物：
  描述：

  对羟基亚苄基丙酮 在 一水合肼 、 溶剂黄146 作用下， 生成 1-[5-(4-hydroxyphenyl)-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone
  参考文献：
  名称：

  Novel dihydropyrazole Derivatives Linked with 4H-Chromene: Microwave-Promoted Synthesis and Antibacterial Activity

  摘要：

  合成了七种新型6-(1-乙酰基-3-甲基-4,5-二氢-1H-吡唑-5-基)-2-氨基-4-取代苯基-4H-苯并吡喃-3-甲腈衍生物，并通过ESI-MS、1H NMR和13C NMR进行了表征。对所有化合物进行了抗菌活性筛选。结果表明，化合物7e和7f对枯草芽孢杆菌ATCC 6633的MIC为1.562μg/mL，显示出显著的活性。

  DOI：

  10.2174/157017810791824847

文献信息

• Synthesis and molecular docking studies of novel 2-chloro-pyridine derivatives containing flavone moieties as potential antitumor agents
  作者：Xin-Hua Liu、Hui-Feng Liu、Xu Shen、Bao-An Song、Pinaki S. Bhadury、Hai-Liang Zhu、Jin-Xing Liu、Xing-Bao Qi

  DOI：10.1016/j.bmcl.2010.05.080

  日期：2010.7

  A series of novel 2-chloro-pyridine derivatives containing flavone, chrome or dihydropyrazole moieties as potential telomerase inhibitors were synthesized. The bioassay tests showed that compounds 6e and 6f exhibited some effect against gastric cancer cell SGC-7901 with IC50 values of 22.28 ± 6.26 and 18.45 ± 2.79 μg/mL, respectively. All title compounds were assayed for telomerase inhibition by a

  合成了一系列新的2-氯吡啶衍生物，其中含有黄酮，铬或二氢吡唑部分作为潜在的端粒酶抑制剂。生物测定测试表明，化合物6e和6f对胃癌细胞SGC-7901表现出一定的作用，IC 50值分别为22.28±6.26和18.45±2.79μg/ mL。通过改进的TRAP测定法检测所有标题化合物的端粒酶抑制作用，结果表明化合物6e可以强烈抑制端粒酶，IC 50值为0.8±0.07μM。进行对接模拟以将化合物6e置于端粒酶（3DU6）的活性位点，以确定可能的结合模型。
• Synthesis, Characterization and Microbial Activity of N-Substituted Pyrazolines
  作者：Jyoti Gaba、Sunita Sharma、Geetika Arora、Poonam Sharma

  DOI：10.14233/ajchem.2016.19881

  日期：——

  Acetic acid and propanoic acid were treated with thionyl chloride to give respective acid chlorides, which were then reacted with synthesized pyrazolines using triethylamine as catalyst in dry dichloromethane to give N-acetylated pyrazolines (1b-7b) and N-propanoylated pyrazolines (1c-7c). Synthesized N-substituted pyrazolines were characterized by IR, 1H NMR and 13C NMR spectral studies. Prepared compounds were screened for their microbial activity against Bacillus sp., Pseudomonas sp., Acinetobactor sp. and Klebsiella sp. N-acetylated (7b) and N-propanoylated (7c) pyrazolines having substitution of methoxy group at meta position and hydroxy group at para position of benzene ring were found effective against Bacillus sp., Acinetobactor sp. and Pseudomonas sp. but not against Klebsiella sp. All pyrazolines and N-substituted pyrazolines exhibited less activity than standard ampicillin at all the tested concentrations.

  醋酸和丙酸经过氯化亚硫酰处理生成各自的酸氯，再与合成的吡唑啉在无水二氯甲烷中使用三乙胺作为催化剂反应，生成N-乙酰化吡唑啉（1b-7b）和N-丙酰化吡唑啉（1c-7c）。合成的N-取代吡唑啉通过红外光谱（IR）、1H核磁共振（NMR）和13C核磁共振（NMR）进行表征。所制备的化合物对芽孢杆菌（Bacillus sp.）、铜绿假单胞菌（Pseudomonas sp.）、嗜盐菌（Acinetobacter sp.）和克雷伯氏菌（Klebsiella sp.）的微生物活性进行了筛选。具有甲氧基在间位和羟基在对位的N-乙酰化（7b）和N-丙酰化（7c）吡唑啉显示出对芽孢杆菌、嗜盐菌及铜绿假单胞菌的有效活性，但对克雷伯氏菌无效。所有吡唑啉和N-取代吡唑啉在所有测试浓度下的活性均低于标准青霉素（氨苄青霉素）。
• Synthesis, Structure, and Antibacterial Activity of Novel 5-Arylpyrazole Derivatives
  作者：Xin-Hua Liu、Peng-Cheng Lv、Bo Li、Hai-Liang Zhu、Bao-An Song

  DOI：10.1071/ch07253

  日期：——

  A series of novel 1-(acetyl,carboxamide,carbothioamide)substituted-5-(substituted-phenyl)-3-methy-4,5-dihydropyrazole derivatives have been synthesized and characterized by 1H NMR, IR, ESI-MS, and elemental analysis. Compounds 6h and 6q were further characterized by single crystal X-ray structural analysis. All of the compounds have been screened for their antibacterial potential in vitro against Bacillus subtilis ATCC 6633, Escherichia coli ATCC 35218, Pseudomonas fluorescens ATCC 13525, and Staphylococcus aureus ATCC 6538. Among the tested compounds, some of them display significant activity against the tested strains, and compounds 5ac and 6h show potent activity with a minimum inhibitory concentration value of 1.562 μg mL–1 against B. subtilis ATCC 6633, which is comparable to the positive control penicillin. Structure–effect relationships are also discussed based on the experimental data.

  合成了一系列新型 1-(乙酰基、甲酰胺、硫代甲酰胺)取代-5-(取代苯基)-3-甲基-4,5-二氢吡唑衍生物，并通过 1H NMR、IR、ESI-MS 和元素分析对其进行了表征。化合物 6h 和 6q 通过单晶 X 射线结构分析得到了进一步表征。所有化合物都对枯草杆菌 ATCC 6633、大肠杆菌 ATCC 35218、荧光假单胞菌 ATCC 13525 和金黄色葡萄球菌 ATCC 6538 进行了体外抗菌潜力筛选。其中，化合物 5ac 和 6h 对枯草杆菌 ATCC 6633 的最小抑制浓度值为 1.562 μg mL-1，与阳性对照青霉素相当。根据实验数据还讨论了结构-效应关系。
• Novel dihydropyrazole Derivatives Linked with 4H-Chromene: Microwave-Promoted Synthesis and Antibacterial Activity
  作者：Xin-Hua Liu、Jin-Xin Liu、Lin-Shan Bai、Guo-Lin Lan、Chu-Xiou Pan

  DOI：10.2174/157017810791824847

  日期：2010.9.1

  Seven novel 6-(1-acetyl-3-methyl-4,5-dihydro-1H-pyrazol-5-yl)-2-amino-4-substituted-phenyl-4H-chromene- 3-carbonitrile derivatives were synthesized and characterized by ESI-MS, 1H NMR and 13C NMR. All of the compounds have been screened for their antibacterial activity. The results show that compounds 7e and 7f displayed significant activity with MIC of 1.562 μg/mL against B. subtilis ATCC 6633.

  合成了七种新型6-(1-乙酰基-3-甲基-4,5-二氢-1H-吡唑-5-基)-2-氨基-4-取代苯基-4H-苯并吡喃-3-甲腈衍生物，并通过ESI-MS、1H NMR和13C NMR进行了表征。对所有化合物进行了抗菌活性筛选。结果表明，化合物7e和7f对枯草芽孢杆菌ATCC 6633的MIC为1.562μg/mL，显示出显著的活性。