5-(2,4,6-trimethoxyphenyl)-1H-pyrazole | 1424351-62-1

• 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-(2,4,6-trimethoxyphenyl)-1H-pyrazole
• CAS: 1424351-62-1；220044-68-8
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: JZPLZLPSLNGEEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2,4,6-trimethoxyphenyl)-1H-pyrazole 在 三氟化硼乙醚 、 sodium hydride 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.25h， 生成 (E)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis, characterization andin vitroandin vivoanti-inflammatory evaluation of novel pyrazole-based chalcones

  摘要：

  A series of novel pyrazole-based chalcones have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxyphenyl)-1H-pyrazole (6). The structures of regioisomers 6 and 7 were determined by 2D H-1-H-1 COSY, H-1-C-13 HSQC and H-1-C-13 HMBC experiments. The newly synthesized compounds were tested for their inhibitory activity against COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Moreover, they were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model for acute inflammation and cotton pellet-induced granuloma model for chronic inflammation. All the synthesized compounds showed potential to demonstrate anti-inflammatory activities, of particular interest compounds 10i, 10e, 10f, and 10h were found to be potent anti-inflammatory agents.

  DOI：

  10.3109/14756366.2013.873037
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 在 sodium hydride 、 potassium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 丙酮 、 mineral oil 为溶剂， 反应 13.5h， 生成 5-(2,4,6-trimethoxyphenyl)-1H-pyrazole
  参考文献：
  名称：

  Design, synthesis, characterization andin vitroandin vivoanti-inflammatory evaluation of novel pyrazole-based chalcones

  摘要：

  A series of novel pyrazole-based chalcones have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxyphenyl)-1H-pyrazole (6). The structures of regioisomers 6 and 7 were determined by 2D H-1-H-1 COSY, H-1-C-13 HSQC and H-1-C-13 HMBC experiments. The newly synthesized compounds were tested for their inhibitory activity against COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Moreover, they were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model for acute inflammation and cotton pellet-induced granuloma model for chronic inflammation. All the synthesized compounds showed potential to demonstrate anti-inflammatory activities, of particular interest compounds 10i, 10e, 10f, and 10h were found to be potent anti-inflammatory agents.

  DOI：

  10.3109/14756366.2013.873037

文献信息

• Enaminone-Derived Pyrazoles with Antimicrobial Activity
  作者：Mashooq Ahmad Bhat、Mohamed A. Al-Omar、Ahmed M. Naglah、Abdul Arif Khan

  DOI：10.1155/2019/2467970

  日期：2019.11.7

  A series of pyrazoles derived from the substituted enaminones were synthesized and were evaluated for antimicrobial activity. All the compounds were characterized by the spectral data and elemental analysis. The synthesized compounds were initially screened for their antimicrobial activity against ATCC 6538, NCTC 10400, NCTC 10418, and ATCC 27853. During initial screening, compounds (P1, P6, and P11) presented significant antimicrobial activity through disc diffusion assay. These compounds were further evaluated for antimicrobial activity at different time points against Gram-positive and Gram-negative bacteria and presented significant activity for 6 hours. The activity was found to be greater against Gram-positive bacteria. In contrast at 24 hours, the activity was found only against Gram-positive bacteria except compound (P11), showing activity against both types of bacteria. Compound (P11) was found to have highest activity against both Gram-positive and Gram-negative bacteria.

  一系列由取代烯酮酮合成的吡唑类化合物被合成，并评估其抗微生物活性。所有化合物均通过光谱数据和元素分析进行表征。合成的化合物最初针对ATCC 6538、NCTC 10400、NCTC 10418和ATCC 27853进行了抗微生物活性筛选。在初步筛选中，化合物（P1、P6和P11）通过圆盘扩散法展现出显著的抗微生物活性。这些化合物随后在不同时间点针对革兰氏阳性和阴性细菌进行了抗微生物活性评估，并在6小时内展现出显著活性。活性在革兰氏阳性细菌中表现更强。相反，在24小时内，活性仅在革兰氏阳性细菌中发现，除了化合物（P11）外，后者对两种类型的细菌均表现出活性。化合物（P11）被发现对革兰氏阳性和阴性细菌均具有最高活性。
• Design, synthesis, characterization and anti-inflammatory evaluation of novel pyrazole amalgamated flavones
  作者：Hemant V. Chavan、Babasaheb P. Bandgar、Laxman K. Adsul、Valmik D. Dhakane、Pravin S. Bhale、Vishnu N. Thakare、Vijay Masand

  DOI：10.1016/j.bmcl.2012.12.094

  日期：2013.3

  A series of novel pyrazole amalgamated flavones has been designed and synthesized from 1-methyl-5-(2,4,6-trimethoxy-phenyl)-1H-pyrazole 6. The structures of regioisomers 6 and 7 were resolved by 2D H-1-H-1 COSY, H-1-C-13 HSQC and H-1-C-13 HMBC experiments. The newly synthesized compounds were tested for their in vitro COX inhibition and in vivo carrageenan induced hind paw edema in rats and acetic acid induced vascular permeability in mice. Although the compounds have inhibitory profile against both COX-1 and COX-2, some of the compounds are found to be selective against COX-2, supported by inhibition of paw edema and vascular permeability. Docking studies were also carried out to determine the structural features which sway the anti-inflammatory activity of the tested compounds. The keto and phenolic -OH are major factors that are prominently involved in interaction with COX-2 active site. (C) 2013 Elsevier Ltd. All rights reserved.
• Design, synthesis, characterization and biological evaluation of novel pyrazole integrated benzophenones
  作者：Babasaheb P. Bandgar、Hemant V. Chavan、Laxman K. Adsul、Vishnu N. Thakare、Sadanand N. Shringare、Rafik Shaikh、Rajesh N. Gacche

  DOI：10.1016/j.bmcl.2012.10.031

  日期：2013.2

  A series of novel pyrazole integrated benzophenones (9a-j) have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxy-phenyl)-1H-pyrazole 6. The structures of the regioisomers 6 and 7 were determined by 2D H-1-H-1 COSY, H-1-C-13 HSQC and H-1-C-13 HMBC experiments. The newly synthesized compounds (9a-j) were evaluated for in vivo anti-inflammatory activity by carrageenan paw edema in rats and in vitro COX-1/COX-2 inhibition and antioxidant potential. Among the synthesized compounds, compounds 9b, 9d and 9f, were found to be active anti-inflammatory agents in addition to having potent antioxidant activity. (c) 2012 Elsevier Ltd. All rights reserved.
• Design, synthesis, characterization and<i>in vitro</i>and<i>in vivo</i>anti-inflammatory evaluation of novel pyrazole-based chalcones
  作者：Hemant V. Chavan、Laxman K. Adsul、Amol S. Kotmale、Valmik D. Dhakane、Vishnu N. Thakare、Babasaheb P. Bandgar

  DOI：10.3109/14756366.2013.873037

  日期：2015.1.2

  A series of novel pyrazole-based chalcones have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxyphenyl)-1H-pyrazole (6). The structures of regioisomers 6 and 7 were determined by 2D H-1-H-1 COSY, H-1-C-13 HSQC and H-1-C-13 HMBC experiments. The newly synthesized compounds were tested for their inhibitory activity against COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Moreover, they were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model for acute inflammation and cotton pellet-induced granuloma model for chronic inflammation. All the synthesized compounds showed potential to demonstrate anti-inflammatory activities, of particular interest compounds 10i, 10e, 10f, and 10h were found to be potent anti-inflammatory agents.