(S)-N-((R)-2-Hydroxy-1-phenyl-ethyl)-2-methoxy-2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionamide | 919361-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-N-((R)-2-Hydroxy-1-phenyl-ethyl)-2-methoxy-2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionamide
• 英文别名: (2S)-N-[(1R)-2-hydroxy-1-phenylethyl]-2-methoxy-2-methyl-3-[6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl]propanamide
• CAS: 919361-20-9
• 化学式: C₃₀H₃₃N₃O₅
• 分子量: 515.609
• InChiKey: YTCUZSGHBMCIEO-YZNIXAGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-N-((R)-2-Hydroxy-1-phenyl-ethyl)-2-methoxy-2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionamide 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以96%的产率得到2-methoxy-2-methyl-3-{6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl}propanoic acid
  参考文献：
  名称：

  Pyridine-3-propanoic acids: Discovery of dual PPARα/γ agonists as antidiabetic agents

  摘要：

  A series of novel pyridine-3-propanoic acids was synthesized. A structure-activity relationship study of these compounds led to the identification of potent dual PPARalpha/gamma agonists with varied isoform selectivity. Based on the results of efficacy studies in diabetic (db/db) mice, and the desired pharmacokinetic parameters, compounds (S)-14 and (S)-19 were selected for further profiling.

  DOI：

  10.1016/j.bmcl.2006.08.110
• 作为产物：
  描述：

  2-(5-甲基-2-苯基-1,3-恶唑-4-基)-1-乙醇 在 lithium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 草酰氯 、 potassium tert-butylate 、 sodium hexamethyldisilazane 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 44.0h， 生成 (S)-N-((R)-2-Hydroxy-1-phenyl-ethyl)-2-methoxy-2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionamide
  参考文献：
  名称：

  Pyridine-3-propanoic acids: Discovery of dual PPARα/γ agonists as antidiabetic agents

  摘要：

  A series of novel pyridine-3-propanoic acids was synthesized. A structure-activity relationship study of these compounds led to the identification of potent dual PPARalpha/gamma agonists with varied isoform selectivity. Based on the results of efficacy studies in diabetic (db/db) mice, and the desired pharmacokinetic parameters, compounds (S)-14 and (S)-19 were selected for further profiling.

  DOI：

  10.1016/j.bmcl.2006.08.110

文献信息

• Synthesis of 2-methoxy-2-methyl-3-{6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl}propanoic acid, a dual PPARα/γ agonist
  作者：Paul S. Humphries、Quyen-Quyen T. Do、David M. Wilhite

  DOI：10.1016/j.tetlet.2009.01.113

  日期：2009.4

  Large quantities of an enantiomerically Pure novel dual PPAR alpha/gamma against were required. Three routes were successfully developed to achieve this goal, with the chosen route utilized to deliver 40 g of material. (C) 2009 Elsevier Ltd. All rights reserved.