3-(4-nitrophenyl)-1-(2,6-dimethylpyrimidin-4-yl)pyrazole-4-aldoxime | 1338825-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-nitrophenyl)-1-(2,6-dimethylpyrimidin-4-yl)pyrazole-4-aldoxime
• 英文别名: N-[[1-(2,6-dimethylpyrimidin-4-yl)-3-(4-nitrophenyl)pyrazol-4-yl]methylidene]hydroxylamine
• CAS: 1338825-15-2
• 化学式: C₁₆H₁₄N₆O₃
• 分子量: 338.326
• InChiKey: QHKGPFIUJPVOME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  119.33
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(4-nitrophenyl)-1-(2,6-dimethylpyrimidin-4-yl)pyrazole-4-aldoxime 在 乙酸酐 作用下， 反应 0.5h， 以71%的产率得到3-(4-nitrophenyl)-1-(2,6-dimethylpyrimidin-4-yl)-4-cyanopyrazole
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of some new 4-substituted-3-aryl-1-(2,6-dimethylpyrimidin-4-yl)pyrazoles

  摘要：

  AbstractSynthesis of a series of new 4‐substituted‐3‐aryl‐1‐(2,6‐dimethylpyrimidin‐4‐yl)pyrazoles (2a, 2b, 2c, 2d, 2e, 2f, 2g, 3a, 3b, 3c, 3d, 3e, 3f, 3g, and 4a, 4b, 4c, 4d, 4e, 4f, 4g) is described. All the synthesized compounds were evaluated in vitro for their antibacterial activity against two gram‐positive and two gram‐negative bacteria, namely, Bacillus subtilis (MTCC 8509), Bacillus stearothermophilus (MTCC 8508), Escherichia coli (MTCC 51), and Pseudomonas putida (MTCC 121), and their activity was compared with two commercial antibiotics, streptomycin and chloramphenicol. Two compounds, namely, 3‐(4‐anisyl)‐1‐(2,6‐dimethylpyrimidin‐4‐yl)pyrazole‐4‐carboxaldehyde (2b) and 3‐(2‐thienyl)‐1‐(2,6‐dimethyl pyrimidin‐4‐yl)pyrazole‐4‐carboxaldehyde (2g) were found to be equipotent to streptomycin and chloramphenicol against gram‐negative bacteria, E. coli having minimum inhibitory concentration (MIC) value = 4 μg/mL. Compounds 4b and 4d also displayed good activity against E. coli with MIC = 8 μg/mL. J. Heterocyclic Chem., (2011).

  DOI：

  10.1002/jhet.701
• 作为产物：
  描述：

  4-肼-2,6-二甲基嘧啶 在 盐酸羟胺 、 sodium acetate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 3-(4-nitrophenyl)-1-(2,6-dimethylpyrimidin-4-yl)pyrazole-4-aldoxime
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of some new 4-substituted-3-aryl-1-(2,6-dimethylpyrimidin-4-yl)pyrazoles

  摘要：

  AbstractSynthesis of a series of new 4‐substituted‐3‐aryl‐1‐(2,6‐dimethylpyrimidin‐4‐yl)pyrazoles (2a, 2b, 2c, 2d, 2e, 2f, 2g, 3a, 3b, 3c, 3d, 3e, 3f, 3g, and 4a, 4b, 4c, 4d, 4e, 4f, 4g) is described. All the synthesized compounds were evaluated in vitro for their antibacterial activity against two gram‐positive and two gram‐negative bacteria, namely, Bacillus subtilis (MTCC 8509), Bacillus stearothermophilus (MTCC 8508), Escherichia coli (MTCC 51), and Pseudomonas putida (MTCC 121), and their activity was compared with two commercial antibiotics, streptomycin and chloramphenicol. Two compounds, namely, 3‐(4‐anisyl)‐1‐(2,6‐dimethylpyrimidin‐4‐yl)pyrazole‐4‐carboxaldehyde (2b) and 3‐(2‐thienyl)‐1‐(2,6‐dimethyl pyrimidin‐4‐yl)pyrazole‐4‐carboxaldehyde (2g) were found to be equipotent to streptomycin and chloramphenicol against gram‐negative bacteria, E. coli having minimum inhibitory concentration (MIC) value = 4 μg/mL. Compounds 4b and 4d also displayed good activity against E. coli with MIC = 8 μg/mL. J. Heterocyclic Chem., (2011).

  DOI：

  10.1002/jhet.701

文献信息

• Targeting the Prostaglandin F2α Receptor for Preventing Preterm Labor with Azapeptide Tocolytics
  作者：Carine B. Bourguet、Eugénie Goupil、Danaë Tassy、Xin Hou、Eryk Thouin、Felix Polyak、Terence E. Hébert、Audrey Claing、Stéphane A. Laporte、Sylvain Chemtob、William D. Lubell

  DOI：10.1021/jm200608k

  日期：2011.9.8

  The prostaglandin-F2 alpha (PGF2 alpha) receptor (FP) was targeted to develop tocolytic agents for inhibiting preterm labor. Azabicycloalkane and azapeptide mimics 2-10 were synthesized based on the (3S,6S,9S)-indolizidin-2-one amino acid analogue PDC113.824 (1), which was shown to modulate FP by a biased allosteric mechanism, involving both G alpha q- and G alpha 12-mediated signaling pathways, and exhibited significant tocolytic activity delaying preterm labor in a mouse model (Goupil; J. Biol. Chem. 2010, 285,25624-25636), Although changes in azabicycloalkane stereochemistry and ring size caused loss of activity, replacement of the indolizidin-2-one amino acid with azaGly-Pro and azaPhe-Pro gave azapeptides 6 and 8, which reduced PGF2 alpha-induced myometrial contractions, potentiated the effect of PGF2 alpha on G alpha q-mediated ERK1/2 activation, and inhibited FP modulation of cell ruffling, a response dependent on the G alpha 12/RhoA/ROCK signaling pathway. Revealing complementarities of azabicycloalkane and azapeptide mimics, novel probes, and efficient tocolytic agents were made to study allosteric modulation of the FP receptor.