2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid | 1195961-07-9

• 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: 2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid
• 英文别名: 2-(5-oxo-2-sulfanylideneimidazolidin-1-yl)-3-phenylpropanoic acid
• CAS: 1195961-07-9
• 化学式: C₁₂H₁₂N₂O₃S
• 分子量: 264.305
• InChiKey: MTXHXOSEHUXYOV-UHFFFAOYSA-N

物化性质

• 沸点：
  438.1±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 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：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid 在 氯化铵 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 β-丙氨酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-(4-((5-(3,4-dichlorophenyl)furan-2-yl)methylene)-5-oxo-2-thioxoimidazolidin-1-yl)-N-(methylsulfonyl)-3-phenylpropanamide
  参考文献：
  名称：

  Discovery of Novel Putative Inhibitors of UDP-GlcNAc 2-Epimerase as Potent Antibacterial Agents

  摘要：

  We present the discovery and optimization of a novel series of inhibitors of bacterial UDP-N-acetylglucosamine 2-epimerase (called 2-epimerase in this letter). Starting from virtual screening hits, the activity of various inhibitory molecules was optimized using a combination of structure-based and rational design approaches. We successfully designed and identified a 2-epimerase inhibitor (compound 12-ES-Na, that we named Epimerox), which blocked the growth of methicillin-resistant Staphylococcus aureus (MRSA) at 3.9 mu M MIC (minimum inhibitory concentration) and showed potent broad range activity against all Gram-positive bacteria that were tested. Additionally a microplate coupled assay was performed to further confirm that the 2-epimerase inhibition of Epimerox was through a target specific mechanism. Furthermore, Epimerox demonstrated in vivo efficacy and had a pharmacokinetic profile that is consonant with it being developed into a promising new antibiotic agent for treatment of infections caused by Gram-positive bacteria.

  DOI：

  10.1021/ml4001936
• 作为产物：
  描述：

  glycylphenylalanine 、 N,N'-硫羰基二咪唑 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以66%的产率得到2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid
  参考文献：
  名称：

  Oxo-Imidazolyl Compounds

  摘要：

  由化学式I和II代表的化合物，或其药用可接受的盐：抑制细菌2-表皮酶，是有用的抗感染剂。

  公开号：

  US20090298900A1

文献信息

• Oxo-Imidazolyl Compounds
  申请人：Bearss David J.

  公开号：US20090298900A1

  公开（公告）日：2009-12-03

  Compounds represented by Formula I and II, or pharmaceutically acceptable salts thereof: inhibit bacterial 2-epimerase and are useful anti-infective agents.

  由化学式I和II代表的化合物，或其药用可接受的盐：抑制细菌2-表皮酶，是有用的抗感染剂。
• Oxo-imidazolyl compounds
  申请人：Bearss David J.

  公开号：US08759384B2

  公开（公告）日：2014-06-24

  Compounds represented by Formula I and II, or pharmaceutically acceptable salts thereof: inhibit bacterial 2-epimerase and are useful anti-infective agents.

  公式I和II所代表的化合物，或其药学上可接受的盐：抑制细菌2-表异构酶并且是有用的抗感染剂。
• OXO-IMIDAZOLYL COMPOUNDS HAVING ANTIBACTERIAL ACTIVITY
  申请人：Astex Pharmaceuticals, Inc.

  公开号：EP2285802B1

  公开（公告）日：2015-11-11
• INHIBITION OF ANTIMICROBIAL TARGETS WITH REDUCED POTENTIAL FOR RESISTANCE
  申请人：The Rockefeller University

  公开号：US20140073639A1

  公开（公告）日：2014-03-13

  The application describes targets and methods that can inhibit bacterial growth in Gram-positive and Gram-negative bacteria. A bacterial enzyme, 2-epimerase, is common to both Gram-positive and Gram-negative bacteria and contains an allosteric site that can be targeted to disrupt the enzyme. The allosteric site is present on the bacterial 2-epimerase, but the analogous mammalian enzyme does not contain the allosteric site, providing a route for attacking bacterial infections without affecting the mammalian enzyme.
• US8759384B2
  申请人：——

  公开号：US8759384B2

  公开（公告）日：2014-06-24