2-(2-(3-methoxyphenyl)-5-methyloxazol-4-yl)ethanol | 518343-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-(3-methoxyphenyl)-5-methyloxazol-4-yl)ethanol
• 英文别名: 2-[2-(3-Methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethanol
• CAS: 518343-85-6
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: UCQWRMQOTPGPTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  408.7±55.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(3-methoxyphenyl)-5-methyloxazol-4-yl)ethanol 在 lithium hydroxide 、 三苯基膦 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-(5-{2-[2-(3-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}-2,3-dihydro-1H-inden-1-yl)butanoic acid
  参考文献：
  名称：

  Substituted indanylacetic acids as PPAR-α–γ activators

  摘要：

  A series of oxazole-substituted indanylacetic acids were prepared which show a spectrum of activity as ligands for PPAR nuclear receptor subtypes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.008
• 作为产物：
  描述：

  间甲氧基苯甲酰氯 在 吡啶 、 氢氧化钾 、 硼烷四氢呋喃络合物 、 sodium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 8.5h， 生成 2-(2-(3-methoxyphenyl)-5-methyloxazol-4-yl)ethanol
  参考文献：
  名称：

  Application of the Dakin−West Reaction for the Synthesis of Oxazole-Containing Dual PPARα/γ Agonists

  摘要：

  An improved method for the preparation of a series of oxazole-containing dual PPARalpha/gamma agonists is described. A synthetic sequence utilizing a Dakin-West reaction was devised that allows for the introduction of the oxazole ring either late in the synthetic sequence via aminomalonate-derived chemistry or in pivotal SAR intermediates derived from aspartic acid.

  DOI：

  10.1021/jo026655v

文献信息

• Synthesis and evaluation of a series of benzopyran derivatives as PPAR α/γ agonists
  作者：Juanhong Yu、Lei Tang、Yushe Yang、Ruyun Ji

  DOI：10.1016/j.ejmech.2008.01.029

  日期：2008.11

  A series of benzopyran derivatives were synthesized and evaluated for PPAR alpha/gamma agonist activities. Most of the compounds exhibit reasonable PPAR alpha and PPAR gamma agonist activities. In particular, compounds 7b, 8b, 8e and 8h with remarkable PPARg EC(50) values of 0.001microM are excellent full PPAR gamma agonists with the functional potency about 130, 20 times stronger than that of leading

  合成了一系列苯并吡喃衍生物，并评估了其对PPARα/γ激动剂的活性。大多数化合物表现出合理的PPARα和PPARγ激动剂活性。特别是，具有显着的PPARg EC（50）值为0.001microM的化合物7b，8b，8e和8h是出色的全PPARγ激动剂，其功能效价分别比前导化合物5和罗格列酮强130倍，20倍。化合物7a，7c，7d和8a是双重PPARα/γ激动剂，与相应的阳性对照相比，所有化合物均具有相当或更高的PPARα/γ激动剂功效。
• Design, synthesis and insulin-sensitizing activity of indomethacin and diclofenac derivatives
  作者：Jiquan Zhang、Jianta Wang、Haoshu Wu、Yaoyao He、Gaofeng Zhu、Xing Cui、Lei Tang

  DOI：10.1016/j.bmcl.2009.04.050

  日期：2009.6

  A series of aromatic acetic acid compounds were designed and synthesized on the basis of Non-steroidal anti-inflammatory drugs indomethacin and diclofenac. Compounds 5a, 7a, 5h, 7h and 17 could strongly promote insulin-regulated differentiation of 3T3-L1 cells in vitro. They acted as full or partial PPAR gamma agonist, or improved insulin resistance through non-PPAR gamma pathway. (C) 2009 Elsevier Ltd. All rights reserved.
• Pyridine-3-propanoic acids: Discovery of dual PPARα/γ agonists as antidiabetic agents
  作者：Paul S. Humphries、Simon Bailey、Jonathon V. Almaden、Sandra J. Barnum、Thomas J. Carlson、Lance C. Christie、Quyen-Quyen T. Do、James D. Fraser、Mary Hess、Jack Kellum、Young H. Kim、Guy A. McClellan、Kathleen M. Ogilvie、Brett H. Simmons、Donald Skalitzky、Shaoxian Sun、David Wilhite、Luke R. Zehnder

  DOI：10.1016/j.bmcl.2006.08.110

  日期：2006.12

  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.
• Pyridine-2-propanoic acids: Discovery of dual PPARα/γ agonists as antidiabetic agents
  作者：Paul S. Humphries、Jonathon V. Almaden、Sandra J. Barnum、Thomas J. Carlson、Quyen-Quyen T. Do、James D. Fraser、Mary Hess、Young H. Kim、Kathleen M. Ogilvie、Shaoxian Sun

  DOI：10.1016/j.bmcl.2006.08.105

  日期：2006.12

  A series of novel pyridine-2-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, compound (S)-13 was selected for further profiling.
• Indanylacetic acids as PPAR-δ activator insulin sensitizers
  作者：Philip Wickens、Chengzhi Zhang、Xin Ma、Qian Zhao、John Amatruda、William Bullock、Michael Burns、Louis-David Cantin、Chih-Yuan Chuang、Thomas Claus、Miao Dai、Fernando Dela Cruz、David Dickson、Frederick J. Ehrgott、Dongping Fan、Sarah Heald、Martin Hentemann、Christiana I. Iwuagwu、Jeffrey S. Johnson、Ellalahewage Kumarasinghe、David Ladner、Rico Lavoie、Sidney Liang、James N. Livingston、Derek Lowe、Steve Magnuson、Gretchen Mannelly、Ingo Mugge、Herbert Ogutu、Susan Pleasic-Williams、Robert W. Schoenleber、Jeff Shapiro、Tatiana Shelekhin、Laurel Sweet、Christopher Town、Manami Tsutsumi

  DOI：10.1016/j.bmcl.2007.03.057

  日期：2007.8

  A series of indane acetic acid derivatives were prepared which show a spectrum of activity as insulin sensitizers and PPAR-ot and PPAR-delta ligands. In vivo data are presented for insulin sensitizers with selectivity for PPAR-delta over PPAR-Oc. (c) 2007 Published by Elsevier Ltd.