5-[(2S)-2-[(4R)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]butyl]-2-methoxybenzaldehyde | 1081111-03-6

• 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: 5-[(2S)-2-[(4R)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]butyl]-2-methoxybenzaldehyde
• CAS: 1081111-03-6
• 化学式: C₂₃H₂₅NO₅
• 分子量: 395.455
• InChiKey: LOZWKDAEDMBFNI-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(2S)-2-[(4R)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]butyl]-2-methoxybenzaldehyde 、 4-(4-chlorophenoxy)benzamide 在 三乙基硅烷 、 lithium hydroxide monohydrate 、 双氧水 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 53.5h， 生成 (S)-2-(3-((4-(4-chlorophenoxy)benzamido)methyl)-4-methoxybenzyl)butanoic acid
  参考文献：
  名称：

  Structure-based design, synthesis, and nonalcoholic steatohepatitis (NASH)-preventive effect of phenylpropanoic acid peroxisome proliferator-activated receptor (PPAR) α-selective agonists

  摘要：

  A series of alpha-ethylphenylpropanoic acid derivatives was prepared as candidate peroxisome proliferator-activated receptor (PPAR) alpha-selective agonists, based on our PPAR alpha/delta dual agonist 3 as a lead compound. Structure-activity relationship studies clearly indicated that the steric bulkiness and position of the distal hydrophobic tail part are critical for PPAR alpha agonistic activity and PPAR alpha selectivity, as had been predicted from a molecular-modeling study. A representative compound blocked the progression of nonalcoholic steatohepatitis (NASH) in an animal model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.064

文献信息

• Structure-Based Design and Synthesis of Fluorescent PPAR.ALPHA./.DELTA. Co-agonist and Its Application as a Probe for Fluorescent Polarization Assay of PPAR.DELTA. Ligands
  作者：Yoko Araya、Jun-ichi Kasuga、Kenji Toyota、Yuko Hirakawa、Takuji Oyama、Makoto Makishima、Kosuke Morikawa、Yuichi Hashimoto、Hiroyuki Miyachi

  DOI：10.1248/cpb.56.1357

  日期：——

  Based on the result of X-ray crystallographic analysis of our peroxisome proliferator-activated receptor alpha and delta (PPARα/δ) co-agonist complexed with human PPAR ligand binding domain (LBD), we designed and synthesized an optically active fluorescent PPARα/δ co-agonist, which has a pyrene unit incorporated directly at the hydrophobic tail part of the structure as a fluorophore. This fluorescent co-agonist was applied in a homogeneous fluorescent polarization assay format for the identification of PPARδ ligands.

  根据过氧化物酶体增殖物激活受体α和δ（PPARα/δ）与人类PPAR配体结合域（LBD）的X射线晶体分析结果，我们设计并合成了一种具有光学活性的荧光PPARα/δ共激动剂，该共激动剂在结构的疏水尾部直接结合了一个芘单元作为荧光团。这种荧光共激动剂被用于均相荧光偏振测定法，用于鉴定PPARδ配体。