N-(tert-butyl)-2-oxo-3-phenylpropanamide | 31334-63-1

• 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: N-(tert-butyl)-2-oxo-3-phenylpropanamide
• 英文别名: 3-Phenyl-α-keto-propionsaeure-N-tert.-butylamid；N-tert-butyl-2-oxo-3-phenylpropanamide
• CAS: 31334-63-1
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: OUUQYPFDOJVDGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-Hydroxy-3-phenyl-(N-tert-butyl)-propionamid 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(tert-butyl)-2-oxo-3-phenylpropanamide
  参考文献：
  名称：

  Synthesis and biological evaluation of α-ketoamides as inhibitors of the Dengue virus protease with antiviral activity in cell-culture

  摘要：

  The development of small molecule inhibitors of the viral protease is of considerable interest for the treatment of emergent flaviviral diseases such as Dengue or West Nile fever. Until today little progress has been made in finding drug-like compounds that inhibit the protease and provide a starting point for lead optimization. We describe here the initial steps of a drug discovery effort that focused on the styryl pharmacophore, combined with a ketoamide function to serve as electrophilic trap for the catalytic serine. This resulted in a fragment-like lead compound with reasonable target affinity and good ligand efficiency, which was extensively modified to explore structure-activity relationships. Selected compounds were cross-tested against the West Nile virus protease and thrombin, indicating that selectivity for one or more flaviviral proteases can be achieved. Finally, the antiviral activity of several protease inhibitors was confirmed in a cell-culture model of Dengue virus replication. The SAR presented here may serve as starting point for further drug discovery efforts with the aim of targeting flaviviral proteases. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.015

文献信息

• Palladium-Catalyzed Multicomponent Reaction of Alkynes, Carboxylic Acids, and Isocyanides: A Direct Approach to Captodative Olefins
  作者：Mingchun Gao、Minfen Zou、Jue Wang、Qitao Tan、Bingxin Liu、Bin Xu

  DOI：10.1021/acs.orglett.9b00137

  日期：2019.3.15

  A palladium-catalyzed multicomponent reaction of alkynes, carboxylic acids, and isocyanides has been developed with the assistance of silver salt under mild conditions. Highly functionalized captodative olefins are synthesized efficiently by this method, which can find many applications as versatile synthons in organic synthesis.

  在银盐的帮助下，在温和的条件下开发了炔烃，羧酸和异氰酸酯的钯催化多组分反应。通过这种方法可以高效地合成高度官能化的巯基化烯烃，可以作为有机合成中的通用合成子获得许多应用。
• US4224226A
  申请人：——

  公开号：US4224226A

  公开（公告）日：1980-09-23
• US4228082A
  申请人：——

  公开号：US4228082A

  公开（公告）日：1980-10-14
• Synthesis and biological evaluation of α-ketoamides as inhibitors of the Dengue virus protease with antiviral activity in cell-culture
  作者：Christian Steuer、Christian Gege、Wolfgang Fischl、Karl H. Heinonen、Ralf Bartenschlager、Christian D. Klein

  DOI：10.1016/j.bmc.2011.05.015

  日期：2011.7

  The development of small molecule inhibitors of the viral protease is of considerable interest for the treatment of emergent flaviviral diseases such as Dengue or West Nile fever. Until today little progress has been made in finding drug-like compounds that inhibit the protease and provide a starting point for lead optimization. We describe here the initial steps of a drug discovery effort that focused on the styryl pharmacophore, combined with a ketoamide function to serve as electrophilic trap for the catalytic serine. This resulted in a fragment-like lead compound with reasonable target affinity and good ligand efficiency, which was extensively modified to explore structure-activity relationships. Selected compounds were cross-tested against the West Nile virus protease and thrombin, indicating that selectivity for one or more flaviviral proteases can be achieved. Finally, the antiviral activity of several protease inhibitors was confirmed in a cell-culture model of Dengue virus replication. The SAR presented here may serve as starting point for further drug discovery efforts with the aim of targeting flaviviral proteases. (C) 2011 Elsevier Ltd. All rights reserved.