methyl 3-[4-[(5S)-5-(acetamidomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl]pyrazole-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 3-[4-[(5S)-5-(acetamidomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl]pyrazole-1-carboxylate
• 英文别名: methyl 3-[4-[(5S)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]pyrazole-1-carboxylate
• 化学式: C₁₇H₁₇FN₄O₅
• 分子量: 376.344
• InChiKey: XDTKZDYERNFCCQ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-[((5S)-3-{4-[(E)-3-(dimethylamino)-2-propenoyl]-3-fluorophenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 生成 methyl 3-[4-[(5S)-5-(acetamidomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl]pyrazole-1-carboxylate
  参考文献：
  名称：

  Carbon–carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria

  摘要：

  In an effort to expand the spectrum of activity of the oxazolidinone class of antibacterial agents to include Gram-negative bacteria, a series of new carbon-carbon linked pyrazolylphenyl analogues has been prepared. The alpha -N-substituted methyl pyrazole (10 alpha) in the C3-linked series exhibited very good Gram-positive activity with MICs less than or equal to 0.5-1 mug/mL and moderate Gramnegative activity with MICs = 2-8 mug/mL against Haemophilus influence and Moraxella catarrhalis. This analogue was also found to have potent in vivo activity with an ED50 = 1.9 mg/kg. beta -Substitution at the C3-linked pyrazole generally results in a loss of activity. The C4-linked pyrazoles are slightly more potent than their counterparts in the C3-linked series. Most of the analogues in the C4-linked series exhibited similar levels of activity in vitro, but lower levels of activity in vivo than 10 alpha. In addition, incorporation of a thioamide moiety in selected C4-linked pyrazole analogues results in an enhancement of in vitro activity leading to compounds several times more potent than eperezolid. linezolid and vancomycin. The thioamide of the N-cyanomethyl pyrazole analogue (34) exhibited an exceptional in vitro activity with MICs of less than or equal to 0.06-0.25 kg/mL against Gram-positive pathogens and with MICs of 1 mug/mL against fastidious Gram-negative pathogens. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00233-4