4,5-dimethyl-2-(4-(2-propyl)-phenyl)-oxazole 3-oxide | 870539-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-dimethyl-2-(4-(2-propyl)-phenyl)-oxazole 3-oxide
• 英文别名: 4,5-dimethyl-3-oxido-2-(4-propan-2-ylphenyl)-1,3-oxazol-3-ium
• CAS: 870539-64-3
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: NKIQLQNQMMVKNS-UHFFFAOYSA-N

物化性质

• 沸点：
  358.9±52.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dimethyl-2-(4-(2-propyl)-phenyl)-oxazole 3-oxide 在 氢氧化钾 、 三氯氧磷 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 生成 rac-2-ethoxy-3-{1-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethyl]-1H-indol-5-yl}propionic acid
  参考文献：
  名称：

  Structure-based design of indole propionic acids as novel PPARα/γ co-agonists

  摘要：

  In the quest for novel PPARalpha/gamma co-agonists as putative drugs for the treatment of type 2 diabetes and dyslipidemia, we have used a structure-based design approach to identify propionic acids with a 1,5-disubstituted indole scaffold as potent PPARalpha/gamma activators. Compounds 13, 24, and 28 are examples of submicromolar dual agonists with different alpha/gamma EC50 ratios that are selective against the delta-isoform. Analysis of the X-ray complex structure of PPARgamma with the indole propionic acid 13 provides a rationalization for some of the observed SAR.

  DOI：

  10.1016/j.bmcl.2006.05.007
• 作为产物：
  描述：

  2,3-丁二酮,单肟,(E)- 、 4-异丙基苯甲醛 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 4,5-dimethyl-2-(4-(2-propyl)-phenyl)-oxazole 3-oxide
  参考文献：
  名称：

  Diarylcycloalkyl derivatives, processes for their preparation and their use as pharmaceuticals

  摘要：

  公开了二芳基环烷基衍生物及其生理上可接受的盐和生理功能衍生物。这些化合物包括式I的那些，其中基团如所定义的，并公开了它们的生理上可接受的盐和制备过程。这些化合物通常具有降脂和/或三酸甘油酯降低性，并且适用于治疗脂质代谢紊乱、II型糖尿病和X综合征等疾病。

  公开号：

  US20050267177A1

文献信息

• Diarylcycloalkyl derivatives, processes for their preparation and their use as pharmceuticals
  申请人：Sanofi-Aventis Deutschland GmbH

  公开号：US07399777B2

  公开（公告）日：2008-07-15

  Diarylcycloalkyl derivatives and their physiologically acceptable salts and physiologically functional derivatives are disclosed. The compounds include those of formula I, in which the radicals are as defined, and their physiologically acceptable salts and processes for their preparation. The compounds typically have lipid- and/or triglyceride-lowering properties and are suitable, for example, for the treatment of disorders of lipid metabolism, of type II diabetes, and of syndrome X.

  本文披露了二芳基环烷基衍生物及其生理上可接受的盐和生理功能衍生物。其中化合物包括公式I中的基团，其定义如下，并且还包括它们的生理上可接受的盐和制备它们的过程。这些化合物通常具有降脂和/或降三酰甘油的特性，例如适用于治疗脂质代谢紊乱、II型糖尿病和X综合征等疾病。
• Aleglitazar, a new, potent, and balanced dual PPARα/γ agonist for the treatment of type II diabetes
  作者：Agnes Bénardeau、Jörg Benz、Alfred Binggeli、Denise Blum、Markus Boehringer、Uwe Grether、Hans Hilpert、Bernd Kuhn、Hans Peter Märki、Markus Meyer、Kurt Püntener、Susanne Raab、Armin Ruf、Daniel Schlatter、Peter Mohr

  DOI：10.1016/j.bmcl.2009.03.036

  日期：2009.5

  Design, synthesis, and SAR of novel alpha-alkoxy-beta-arylpropionic acids as potent and balanced PPARalphagamma coagonists are described. One representative thereof, Aleglitazar ((S)-2Aa), was chosen for clinical development. Its X-ray structure in complex with both receptors as well as its high efficacy in animal models of T2D and dyslipidemia are also presented.
• US7399777B2
  申请人：——

  公开号：US7399777B2

  公开（公告）日：2008-07-15
• Diarylcycloalkyl derivatives, processes for their preparation and their use as pharmaceuticals
  申请人：Glombik Heiner

  公开号：US20050267177A1

  公开（公告）日：2005-12-01

  Diarylcycloalkyl derivatives and their physiologically acceptable salts and physiologically functional derivatives are disclosed. The compounds include those of formula I, in which the radicals are as defined, and their physiologically acceptable salts and processes for their preparation. The compounds typically have lipid- and/or triglyceride-lowering properties and are suitable, for example, for the treatment of disorders of lipid metabolism, of type II diabetes, and of syndrome X.

  公开了二芳基环烷基衍生物及其生理上可接受的盐和生理功能衍生物。这些化合物包括式I的那些，其中基团如所定义的，并公开了它们的生理上可接受的盐和制备过程。这些化合物通常具有降脂和/或三酸甘油酯降低性，并且适用于治疗脂质代谢紊乱、II型糖尿病和X综合征等疾病。
• Structure-based design of indole propionic acids as novel PPARα/γ co-agonists
  作者：Bernd Kuhn、Hans Hilpert、Jörg Benz、Alfred Binggeli、Uwe Grether、Roland Humm、Hans Peter Märki、Markus Meyer、Peter Mohr

  DOI：10.1016/j.bmcl.2006.05.007

  日期：2006.8

  In the quest for novel PPARalpha/gamma co-agonists as putative drugs for the treatment of type 2 diabetes and dyslipidemia, we have used a structure-based design approach to identify propionic acids with a 1,5-disubstituted indole scaffold as potent PPARalpha/gamma activators. Compounds 13, 24, and 28 are examples of submicromolar dual agonists with different alpha/gamma EC50 ratios that are selective against the delta-isoform. Analysis of the X-ray complex structure of PPARgamma with the indole propionic acid 13 provides a rationalization for some of the observed SAR.