1,2-Bis-(m-chlorophenyl)-pyrazolidine-3,5-dione | 55138-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-Bis-(m-chlorophenyl)-pyrazolidine-3,5-dione
• 英文别名: 1,2-bis-(3-chloro-phenyl)-pyrazolidine-3,5-dione；1,2-bis(3-chlorophenyl)pyrazolidine-3,5-dione
• CAS: 55138-13-1
• 化学式: C₁₅H₁₀Cl₂N₂O₂
• 分子量: 321.163
• InChiKey: RATWLGHYRIQFQW-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C(Solv: ethanol (64-17-5))
• 沸点：
  460.5±55.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-Bis-(m-chlorophenyl)-pyrazolidine-3,5-dione 、 4-三氟甲基苯基异氰酸酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以37%的产率得到1,2-bis(3-chlorophenyl)-3-hydroxy-5-oxo-N-[4-(trifluoromethyl)phenyl]pyrazole-4-carboxamide
  参考文献：
  名称：

  Pyrazolidine-3,5-diones and 5-Hydroxy-1H-pyrazol-3(2H)-ones, Inhibitors of UDP-N-acetylenolpyruvyl Glucosamine Reductase

  摘要：

  A series of pyrazolidine-3,5-dione and 5-hydroxy-1H-pyrazol-3(2H)-one inhibitors of Escherichia coli UDP-N-acetylenolpyruvyl glucosamine reductase (MurB) has been prepared. The 5-hydroxy-1H-pyrazol-3(2H)ones show low micromolar IC50 values versus E. coli MurB and submicromolar minimal inhibitory concentrations ( MIC) against Staphylococcus aureus GC 1131, Enterococcus faecalis GC 2242, Streptococcus pneumoniae GC 1894, and E. coli GC 4560 imp, a strain with increased outer membrane permeability. None of these compounds show antimicrobial activity against Candida albicans, a marker of eukaryotic toxicity. Moreover, these compounds inhibit peptidoglycan biosynthesis, as assessed by measuring the amount of soluble peptidoglycan produced by Streptococcus epidermidis upon incubation with compounds. A partial least squares projection to latent structures analysis shows that improving MurB potency and MIC values correlate with increasing lipophilicity of the C-4 substituent of the 5-hydroxy-1H-pyrazol-3(2H)-one core. Docking studies using FLO and PharmDock produced several binding orientations for these molecules in the MurB active site.

  DOI：

  10.1021/jm060499t
• 作为产物：
  描述：

  3-氯苯胺 在 manganese(IV) oxide 、 sodium ethanolate 、 氯化铵 、 锌 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 17.5h， 生成 1,2-Bis-(m-chlorophenyl)-pyrazolidine-3,5-dione
  参考文献：
  名称：

  Pyrazolidine-3,5-diones and 5-Hydroxy-1H-pyrazol-3(2H)-ones, Inhibitors of UDP-N-acetylenolpyruvyl Glucosamine Reductase

  摘要：

  A series of pyrazolidine-3,5-dione and 5-hydroxy-1H-pyrazol-3(2H)-one inhibitors of Escherichia coli UDP-N-acetylenolpyruvyl glucosamine reductase (MurB) has been prepared. The 5-hydroxy-1H-pyrazol-3(2H)ones show low micromolar IC50 values versus E. coli MurB and submicromolar minimal inhibitory concentrations ( MIC) against Staphylococcus aureus GC 1131, Enterococcus faecalis GC 2242, Streptococcus pneumoniae GC 1894, and E. coli GC 4560 imp, a strain with increased outer membrane permeability. None of these compounds show antimicrobial activity against Candida albicans, a marker of eukaryotic toxicity. Moreover, these compounds inhibit peptidoglycan biosynthesis, as assessed by measuring the amount of soluble peptidoglycan produced by Streptococcus epidermidis upon incubation with compounds. A partial least squares projection to latent structures analysis shows that improving MurB potency and MIC values correlate with increasing lipophilicity of the C-4 substituent of the 5-hydroxy-1H-pyrazol-3(2H)-one core. Docking studies using FLO and PharmDock produced several binding orientations for these molecules in the MurB active site.

  DOI：

  10.1021/jm060499t

文献信息

• MANGIAVACCHI S.; CALISTRI M. T., ANN. CHIM. (ITAL.), 1973, 63, NO 11-12, 799-805
  作者：MANGIAVACCHI S.、 CALISTRI M. T.

  DOI：——

  日期：——