2-(3-bromophenyl)-5-methyl-4-oxazoleacetic acid | 328918-95-2

• 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-(3-bromophenyl)-5-methyl-4-oxazoleacetic acid
• 英文别名: 2-[2-(3-bromophenyl)-5-methyl-1,3-oxazol-4-yl]acetic acid
• CAS: 328918-95-2
• 化学式: C₁₂H₁₀BrNO₃
• 分子量: 296.12
• InChiKey: WVWVSAXKJDDNKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-bromophenyl)-5-methyl-4-oxazoleacetic acid 在 吡啶 、 4-二甲氨基吡啶 、 palladium diacetate 、 sodium hydroxide 、 硼烷 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-{4-[2-(2-Biphenyl-3-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-p-tolyloxy-propionic acid
  参考文献：
  名称：

  Conversion of human-selective PPARα agonists to human/mouse dual agonists: a molecular modeling analysis

  摘要：

  To understand the species selectivity in a series of a-methyl-a-phenoxy carboxylic acid PPARalpha/gamma dual agonists (1-11), structure-based molecular modeling was carried out in the ligand binding pockets of both human and mouse PPARalpha. This study suggested that interaction of both 4-phenoxy and phenyloxazole substituents of these ligands with F272 and M279 in mouse PPARalpha leads to the species-specific divergence in ligand binding. Insights obtained in the molecular modeling studies of these key interactions resulted in the ability to convert a human-selective PPARalpha agonist to a human and mouse dual agonist within the same platform.(C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.031
• 作为产物：
  描述：

  [2-(3-bromophenyl)-5-methyloxazole-4-yl]-acetonitrile 在 氢氧化钾 作用下， 以 乙二醇甲醚 、 水 、 甲苯 为溶剂， 以39.8 g (60%)的产率得到2-(3-bromophenyl)-5-methyl-4-oxazoleacetic acid
  参考文献：
  名称：

  Modulators of peroxisome proliferator activated receptors

  摘要：

  本发明涉及由结构式I表示的化合物及其药学上可接受的盐、溶剂和水合物，以及制备方法、使用方法和具有由结构式I表示的化合物及其药学上可接受的盐、溶剂和水合物的药物组合物：在结构式I中，n为2、3或4；V为O或S；W为O、S或SO2；R1为H、C1-C4烷基、苯基或三氟甲基；R2分别为H、C1-C6烷基、芳基-C1-C6烷基、环烷基-C1-C4烷基、芳基、环烷基，或者与它们结合的苯基一起形成萘基或1,2,3,4-四氢萘基；R3分别为H、C1-C6烷基、芳基-C1-C6烷基、环烷基-C1-C4烷基、芳基或环烷基；R4分别为H、C1-C4烷基、芳基或苄基；R5分别为H、取代或未取代的芳基或杂环烷基，但至少有一个R5是取代或未取代的芳基或取代或未取代的杂环烷基；R6为H、C1-C4烷基或氨基烷基。

  公开号：

  US06417212B1

文献信息

• Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists
  申请人：——

  公开号：US20040024034A1

  公开（公告）日：2004-02-05

  Compounds represented by the following (I), and pharmaceutically acceptable salts, solvates and hydrates thereof, wherein R1 is an unsubstituted or substituted aryl, heteroaryl, cycloalkyl, aryl-alkyl, heteroaryl-alkyl or cycloalkyl-alkyl, R2 is H, alkyl or haloalkyl, the polymethylene chain (II), is saturated or may contain a carbon-carbon double bond, while n is 2, 3, 4, W is O or S, Y is an unsubsituted or substituted phenylene, naphthylene or 1, 2, 3, 4 tetrahydronaphthylene, R3 is H, alkyl or haloalkyl. R4 is H, alkyl, haloalkyl or a substituted or unsubstituted benzyl, are useful for modulating a peroxisome proliferator activated receptor, particularly in the treatment of diabetes mellitus.

  以下化合物（I）及其药用可接受的盐、溶剂化合物和水合物，其中R1是未取代或取代的芳基、杂环芳基、环烷基、芳基-烷基、杂环芳基-烷基或环烷基-烷基，R2是H、烷基或卤代烷基，聚亚甲基链（II）饱和或可能含有碳-碳双键，n为2、3、4，W为O或S，Y是未取代或取代的苯基、萘基或1,2,3,4-四氢萘基，R3是H、烷基或卤代烷基。R4是H、烷基、卤代烷基或取代或未取代的苄基，用于调节过氧化物酶体增殖物激活受体，特别是在糖尿病治疗中是有用的。
• [EN] BIARYL-OXA(THIA)ZOLE DERIVATIVES AND THEIR USE AS PPARS MODULATORS<br/>[FR] DERIVES DE BIARYL-OXA(THIA)ZOLE ET LEUR UTILISATION EN TANT QUE MODULATEURS DE PPAR
  申请人：LILLY CO ELI

  公开号：WO2001016120A1

  公开（公告）日：2001-03-08

  Compounds represented by Formula (I) wherein n is 2, 3, or 4; V is O or S; W is O, S, or SO2 and at least one R5 is a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl; are modulators of peroxisome proliferator activated receptors and are useful in the treatment of type II diabetes and of cardiovascular diseases.

  公式（I）所代表的化合物中，其中n为2、3或4；V为O或S；W为O、S或SO2，且至少有一个R5为取代或未取代的芳基或取代或未取代的杂环基；是过氧化物酶体增殖物激活受体的调节剂，并且在治疗2型糖尿病和心血管疾病方面有用。
• [EN] OXAZOLYL-ARYLPROPIONIC ACID DERIVATIVES AND THEIR USE AS PPAR AGONISTS<br/>[FR] DÉRIVÉS D'ACIDE OXAZOLYL-ARYLPROPIONIQUE ET LEUR UTILISATION COMME AGONISTES DES PPAR
  申请人：LILLY CO ELI

  公开号：WO2002016332A1

  公开（公告）日：2002-02-28

  Novel compounds that are modulators of PPAR receptors, and pharmaceutically acceptable salts, solvates and hydrates thereof, processes for making the compounds, pharmaceutical compositions containing the compounds, or pharmaceutically acceptable salts, solvates and hydrates thereof.

  一种调节PPAR受体的新型化合物，以及其药学上可接受的盐、溶剂化物和水合物，制备该化合物的方法，含有该化合物或其药学上可接受的盐、溶剂化物和水合物的药物组合物。
• Oxazolyl-aryloxyacetic acid derivatives and their use as PPAR agonists
  申请人：Brooks Alisa Dawn

  公开号：US20050250825A1

  公开（公告）日：2005-11-10

  Compounds represented by the following structural formula (I), and pharmaceutically acceptable salts, solvates and hydrates thereof, wherein R1 is an unsubstituted or substituted aryl, heteroaryl, cycloalkyl, aryl-alkyl, heteroaryl-alkyl or cycloalkyl-alkyl, R2 is H, alkyl or haloalkyl, the polymethylene chain (H), is saturated or may contain a carbon-carbon double bond, while n is 2, 3, 4, W is O or S, Y is an unsubstituted phenylene, naphthylene or 1, 2, 3, 4 tetrahydronaphthylene, R3 is H, alkyl or haloalkyl, R4 is H, alkyl, haloalkyl or a substituted or unsubstituted benzyl, are useful for modulating a peroxisome proliferator activated receptor, particularly in the treatment of diabetes mellitus.

  以下结构式（I）所代表的化合物及其药学上可接受的盐、溶剂化合物和水合物，其中R1是未取代或取代的芳基、杂环芳基、环烷基、芳基-烷基、杂环芳基-烷基或环烷基-烷基，R2是氢、烷基或卤代烷基，聚亚甲基链（H）是饱和的或可能含有碳-碳双键，而n为2、3、4，W为O或S，Y为未取代的苯基、萘基或1、2、3、4-四氢萘基，R3是氢、烷基或卤代烷基，R4是氢、烷基、卤代烷基或取代或未取代的苄基，可用于调节过氧化物酶体增殖物激活受体，特别是用于治疗糖尿病。
• OXAZOLYL-ARYLOXYACETIC ACID DERIVATIVES AND THEIR USE AS PPAR AGONISTS
  申请人：Brooks Dawn Alisa

  公开号：US20080146631A1

  公开（公告）日：2008-06-19

  Compounds represented by the following structural formula (I), and pharmaceutically acceptable salts, solvates and hydrates thereof, wherein R1 is an unsubstituted or substituted aryl, heteroaryl, cycloalkyl, aryl-alkyl, heteroaryl-alkyl or cycloalkyl-alkyl, R2 is H, alkyl or haloalkyl, the polymethylene chain (II), is saturated or may contain a carbon-carbon double bond, while n is 2, 3, 4, W is O or S, Y is an unsubstituted or substituted phenylene, naphthylene or 1, 2, 3, 4 tetrahydronaphthylene, R3 is H, alkyl or haloalkyl, R4 is H, alkyl, haloalkyl or a substituted or unsubstituted benzyl, are useful for modulating a preoxisome proliferator activated receptor, particularly in the treatment of diabetes mellitus.

  以下结构式（I）所代表的化合物，以及其药学上可接受的盐、溶剂合物和水合物，其中R1为未取代或取代的芳基、杂环芳基、环烷基、芳基烷基、杂环芳基烷基或环烷基烷基，R2为H、烷基或卤代烷基，多亚甲基链（II）为饱和或含有碳-碳双键，n为2、3、4，W为O或S，Y为未取代或取代的苯基、萘基或1,2,3,4-四氢萘基，R3为H、烷基或卤代烷基，R4为H、烷基、卤代烷基或取代或未取代的苄基。这些化合物对于调节前线体增生激活受体特别是在糖尿病治疗中是有用的。