N-[2,6-bis(1-methylethyl)phenyl]-β-oxo-benzenepropanamide | 150423-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[2,6-bis(1-methylethyl)phenyl]-β-oxo-benzenepropanamide
• 英文别名: N-[2,6-bis(1-methylethyl)phenyl]-beta-oxo-benzenepropanamide；N-[2,6-di(propan-2-yl)phenyl]-3-oxo-3-phenylpropanamide
• CAS: 150423-96-4
• 化学式: C₂₁H₂₅NO₂
• 分子量: 323.435
• InChiKey: HMYWKXTYKRCPFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-丁二酮 、 N-[2,6-bis(1-methylethyl)phenyl]-β-oxo-benzenepropanamide 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 504.0h， 生成
  参考文献：
  名称：

  WO2008/70934

  摘要：

  公开号：
• 作为产物：
  描述：

  2,6-二异丙基苯异氰酸酯 、 苯乙酮 在 lithium diisopropyl amide 作用下， 生成 N-[2,6-bis(1-methylethyl)phenyl]-β-oxo-benzenepropanamide
  参考文献：
  名称：

  Inhibitors of acyl-CoA:cholesterol acyltransferase. 5. Identification and structure-activity relationships of novel .beta.-keto amides as hypocholesterolemic agents

  摘要：

  A study of structure-activity relationships of substituted beta-ketoamide ACAT inhibitors I and II was performed. The results of this study suggest that whereas the beta-keto group was tolerated with no loss in activity, beta-hydroxy and oxime moieties led to significantly reduced activity in vitro and in vivo. The most potent inhibitor from the acyclic series (I) (11, IC50 = 0.006 muM) contained a C-13 alkyl chain. This compound reduced plasma total cholesterol by 38% and 66% at 3 and 30 mg/kg, respectively, in cholesterol-fed rats. Dimethylation alpha to the anilide core(5) and subsequent N-methylation of the amide NH (6) decreased in vitro potency significantly. It was also found that high potency was retained with inhibitors which incorporated the carbonyl into a lactam ring (II).

  DOI：

  10.1021/jm00072a014

文献信息

• Substituted beta-ketoamide ACAT inhibitors
  申请人：Warner-Lambert Company

  公开号：US05278326A1

  公开（公告）日：1994-01-11

  Novel pharmaceutically useful compounds which lower blood cholesterol levels and are beta-ketoamides, oximes, amines, and hydroxyl derivatives thereof.

  一种降低血液胆固醇水平的新型药用化合物，其为β-酮酰胺、肟、胺和其羟基衍生物。
• 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.
• WO2008/70891
  申请人：——

  公开号：——

  公开（公告）日：——
• US5278326A
  申请人：——

  公开号：US5278326A

  公开（公告）日：1994-01-11
• WO2008/70934
  申请人：——

  公开号：——

  公开（公告）日：——