N-[2-chloro-5-(trifluoromethyl)phenyl]-3-oxo-3-phenylpropanamide | 388093-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[2-chloro-5-(trifluoromethyl)phenyl]-3-oxo-3-phenylpropanamide
• CAS: 388093-93-4
• 化学式: C₁₆H₁₁ClF₃NO₂
• mdl: MFCD01248504
• 分子量: 341.717
• InChiKey: YTCWZYBBDZOIDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-chloro-5-(trifluoromethyl)phenyl]-3-oxo-3-phenylpropanamide 、 2,3-丁二酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成
  参考文献：
  名称：

  Synthesis, binding and bioactivity of γ-methylene γ-lactam ecdysone receptor ligands: Advantages of QSAR models for flexible receptors

  摘要：

  Nuclear hormone receptors, such as the ecdysone receptor, often display a large amount of induced fit to ligands. The size and shape of the binding pocket in the EcR subunit changes markedly on ligand binding, making modelling methods such as docking extremely challenging. It is, however, possible to generate excellent 3D QSAR models for a given type of ligand, suggesting that the receptor adopts a relatively restricted number of binding site configurations or 'attractors'. We describe the synthesis, in vitro binding and selected in vivo toxicity data for gamma-methylene gamma-lactams, a new class of high-affinity ligands for ecdysone receptors from Bovicola ovis (Phthiraptera) and Lucilia cuprina (Diptera). The results of a 3D QSAR study of the binding of methylene lactams to recombinant ecdysone receptor protein suggest that this class of ligands is indeed recognised by a single conformation of the EcR binding pocket. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.020
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 3-氨基-4-氯三氟甲苯 反应 2.0h， 以16%的产率得到N-[2-chloro-5-(trifluoromethyl)phenyl]-3-oxo-3-phenylpropanamide
  参考文献：
  名称：

  Synthesis, binding and bioactivity of γ-methylene γ-lactam ecdysone receptor ligands: Advantages of QSAR models for flexible receptors

  摘要：

  Nuclear hormone receptors, such as the ecdysone receptor, often display a large amount of induced fit to ligands. The size and shape of the binding pocket in the EcR subunit changes markedly on ligand binding, making modelling methods such as docking extremely challenging. It is, however, possible to generate excellent 3D QSAR models for a given type of ligand, suggesting that the receptor adopts a relatively restricted number of binding site configurations or 'attractors'. We describe the synthesis, in vitro binding and selected in vivo toxicity data for gamma-methylene gamma-lactams, a new class of high-affinity ligands for ecdysone receptors from Bovicola ovis (Phthiraptera) and Lucilia cuprina (Diptera). The results of a 3D QSAR study of the binding of methylene lactams to recombinant ecdysone receptor protein suggest that this class of ligands is indeed recognised by a single conformation of the EcR binding pocket. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.020

文献信息

• Synthesis, binding and bioactivity of γ-methylene γ-lactam ecdysone receptor ligands: Advantages of QSAR models for flexible receptors
  作者：Woldeamanuel Birru、Ross T. Fernley、Lloyd D. Graham、Julian Grusovin、Ronald J. Hill、Albert Hofmann、Linda Howell、Peter J. James、Karen E. Jarvis、Wynona M. Johnson、Dionne A. Jones、Christa Leitner、Andris J. Liepa、George O. Lovrecz、Louis Lu、Roland H. Nearn、Brian J. O’Driscoll、Tram Phan、Matthew Pollard、Kathleen A. Turner、David A. Winkler

  DOI：10.1016/j.bmc.2010.06.020

  日期：2010.8

  Nuclear hormone receptors, such as the ecdysone receptor, often display a large amount of induced fit to ligands. The size and shape of the binding pocket in the EcR subunit changes markedly on ligand binding, making modelling methods such as docking extremely challenging. It is, however, possible to generate excellent 3D QSAR models for a given type of ligand, suggesting that the receptor adopts a relatively restricted number of binding site configurations or 'attractors'. We describe the synthesis, in vitro binding and selected in vivo toxicity data for gamma-methylene gamma-lactams, a new class of high-affinity ligands for ecdysone receptors from Bovicola ovis (Phthiraptera) and Lucilia cuprina (Diptera). The results of a 3D QSAR study of the binding of methylene lactams to recombinant ecdysone receptor protein suggest that this class of ligands is indeed recognised by a single conformation of the EcR binding pocket. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.