(S)-Pyrrolidine-2-carboxylic acid [(S)-1-carbamoyl-2-(4-hydroxy-phenyl)-ethyl]-amide | 52329-46-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-Pyrrolidine-2-carboxylic acid [(S)-1-carbamoyl-2-(4-hydroxy-phenyl)-ethyl]-amide
• 英文别名: L-Tyrosinamide, L-prolyl-；(2S)-N-[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
• CAS: 52329-46-1
• 化学式: C₁₄H₁₉N₃O₃
• 分子量: 277.323
• InChiKey: FYSOVNFPTBIWBY-RYUDHWBXSA-N

物化性质

• 沸点：
  644.6±55.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-Pyrrolidine-2-carboxylic acid [(S)-1-carbamoyl-2-(4-hydroxy-phenyl)-ethyl]-amide 、 2-(2,4-Dichloro-phenyl)-4-[1-ethoxy-meth-(Z)-ylidene]-4H-oxazol-5-one 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 (2S)-N-[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-1-[(Z)-[2-(2,4-dichlorophenyl)-5-oxo-1,3-oxazol-4-ylidene]methyl]pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Potent and selective inhibitors of bacterial methionyl tRNA synthetase derived from an oxazolone–dipeptide scaffold

  摘要：

  The preparation and structure-activity relationships (SARs) of potent and selective small molecule inhibitors of bacterial methionyl-tRNA synthetase (MetRS) derived from an oxazolone-dipeptide scaffold are described. Examples combine Staphylococcus aureus MetRS (SaMetRS) potency with selectivity over human MetRS. As a result of the SAR expansion compound 14a was identified, as a potent SaMetRS inhibitor (IC50 = 18 nM) having moderate inhibition of MetRS derived from Enterococci faecalis (IC50 = 3.51 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.094

文献信息

• Potent and selective inhibitors of bacterial methionyl tRNA synthetase derived from an oxazolone–dipeptide scaffold
  作者：Manish Tandon、David L Coffen、Paul Gallant、Dennis Keith、Mark A Ashwell

  DOI：10.1016/j.bmcl.2004.01.094

  日期：2004.4

  The preparation and structure-activity relationships (SARs) of potent and selective small molecule inhibitors of bacterial methionyl-tRNA synthetase (MetRS) derived from an oxazolone-dipeptide scaffold are described. Examples combine Staphylococcus aureus MetRS (SaMetRS) potency with selectivity over human MetRS. As a result of the SAR expansion compound 14a was identified, as a potent SaMetRS inhibitor (IC50 = 18 nM) having moderate inhibition of MetRS derived from Enterococci faecalis (IC50 = 3.51 muM). (C) 2004 Elsevier Ltd. All rights reserved.