4-acetyl-3-hydroxy-1-methyl-5-phenyl-1H-pyrrol-2(5H)-one | 165056-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 4-acetyl-3-hydroxy-1-methyl-5-phenyl-1H-pyrrol-2(5H)-one
• 英文别名: 4-acetyl-3-hydroxy-1-methyl-5-phenyl-1,5-dihydro-2H-pyrrol-2-one；3-acetyl-4-hydroxy-1-methyl-2-phenyl-2H-pyrrol-5-one
• CAS: 165056-11-1
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: RKOZYHBRZUQYQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  C.I.酸性橙108 、 4-acetyl-3-hydroxy-1-methyl-5-phenyl-1H-pyrrol-2(5H)-one 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以86%的产率得到
  参考文献：
  名称：

  Gein, V.L.; Shumilovskikh, E.V.; Voronina, E.V., Russian Journal of General Chemistry, 1994, vol. 64, # 7.2, p. 1084 - 1089

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 、 乙酰丙酮酸甲酯 、 甲胺 以 乙醇 、 水 为溶剂， 反应 0.5h， 以77%的产率得到4-acetyl-3-hydroxy-1-methyl-5-phenyl-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Gein, V.L.; Shumilovskikh, E.V.; Voronina, E.V., Russian Journal of General Chemistry, 1994, vol. 64, # 7.2, p. 1084 - 1089

  摘要：

  DOI：

文献信息

• Synthesis and in vitro Evaluation of West Nile Virus Protease Inhibitors Based on the 1,3,4,5‐Tetrasubstituted 1 <i>H</i> ‐Pyrrol‐2(5 <i>H</i> )‐one Scaffold
  作者：Yaojun Gao、Sanjay Samanta、Taian Cui、Yulin Lam

  DOI：10.1002/cmdc.201300244

  日期：2013.9

  1H‐pyrrol‐2(5H)‐one scaffold was identified by screening a small library of nonpeptidic compounds. Optimization of this initial hit by the synthesis and screening of a focused library of compounds with this scaffold led to the identification of a novel uncompetitive inhibitor ((−)‐1a16, IC50=2.2±0.7 μM) of the WNV NS2B–NS3 protease. Molecular docking of the chiral compound onto the WNV protease indicates

  西尼罗河病毒（WNV）是黄病毒科的成员，是一种由蚊子传播的病原体，每年引起大量人类感染。目前尚无可用于人类的针对WNV的疫苗或抗病毒疗法。因此，迫切需要开发针对该病毒的新化学疗法。在这项研究中，通过筛选一个小的非肽类化合物文库，鉴定了具有1,3,4,5-四取代的1 H-吡咯-2（5 H）-one支架的WNV NS2B–NS3蛋白酶抑制剂。该初始命中通过合成的优化和化合物与本支架导致的新颖非竞争性抑制剂的鉴定（（聚焦文库的筛选- ） - 1a16，IC 50 = 2.2±0.7μ中号）的WNV NS2B– 蛋白酶。手性化合物与WNV蛋白酶的分子对接表明1a16的R 对映体干扰了NS2B辅因子和 蛋白酶结构域之间的生产性相互作用，因此是抑制WNV NS2B– 蛋白酶的优选异构体。
• Approach to the Library of 3-Hydroxy-1,5-dihydro-2<i>H</i>-pyrrol-2-ones through a Three-Component Condensation
  作者：Sergey V. Ryabukhin、Dmitriy M. Panov、Andrey S. Plaskon、Oleksandr O. Grygorenko

  DOI：10.1021/co300082t

  日期：2012.12.10

  A convenient procedure for the parallel synthesis of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones through a three-component condensation of active methylene compounds, aldehydes, and amines was developed. It was shown that the use of acetic acid as the reaction medium was suitable for the considerably reactive substrates with no additional functionalities. The substrates with low reactivity and those possessing carboxylic groups or additional basic centers required the use of DMF as the solvent and chlorotrimethylsilane as the reaction promoter was necessary. More than 3000 pyrrolones were synthesized by the developed procedure. To demonstrate the scope of the described approach 114 library representatives were fully characterized.
• Bagrov, Russian Journal of General Chemistry, 1998, vol. 68, # 8, p. 1217 - 1220
  作者：Bagrov

  DOI：——

  日期：——