5-甲基-2-苯基-4-(2-丙烯基)噁唑 | 331746-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-甲基-2-苯基-4-(2-丙烯基)噁唑
• 英文名称: 5-methyl-2-phenyl-4-prop-2-enyloxazole
• 英文别名: 4-allyl-5-methyl-2-phenyl-oxazole；5-methyl-4-allyl-2-phenyloxazole；5-methyl-2-phenyl-4-prop-2-enyl-1,3-oxazole
• CAS: 331746-96-4
• 化学式: C₁₃H₁₃NO
• mdl: MFCD08460990
• 分子量: 199.252
• InChiKey: FNIFVUOVNBTWEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(6-bromopyridin-3-yl)methyl]tetrahydrofuran-2-carboxylate 、 5-甲基-2-苯基-4-(2-丙烯基)噁唑 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三苯胂 9-硼双环[3.3.1]壬烷 、 caesium carbonate 、 双氧水 、 sodium acetate 作用下， 以 四氢呋喃 、 DMF (N,N-dimethyl-formamide) 、 水 为溶剂， 反应 22.0h， 以57%的产率得到2-{6-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-pyridin-3-ylmethyl}-tetrahydro-furan-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  [EN] ALPHA SUBSTITUTED CARBOXYLIC ACID AS PPAR MODULATORS
  [FR] ACIDES CARBOXYLIQUES ALPHA-SUBSTITUES COMME MODULATEURS DU RECEPTEUR ACTIVE PAR LES PROLIFERATEURS DE PEROXYSOME (PPAR)

  摘要：

  式(I)的α-取代羧酸，其中R'和R2如规范中定义，R3为A)式(II)；B)式(III)；C)式(IV)；和D)式(V)；其中Y、Art、Are、AP、R4、R5、R6、R7、R6、R9、R9a、R10、R'、R12、R17、环A和p如规范中定义；含有所述化合物或其盐的有效量的药物组合物对于治疗PPAR，特别是PPAR α/y相关的疾病，如糖尿病、血脂异常、肥胖和炎症性疾病是有用的。

  公开号：

  WO2004092145A1
• 作为产物：
  描述：

  N-(1-acetylbut-3-enyl)benzamide 在 三氟乙酸 、 三氟乙酸酐 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 16.0h， 以95%的产率得到5-甲基-2-苯基-4-(2-丙烯基)噁唑
  参考文献：
  名称：

  Synthesis and evaluation of novel α-heteroaryl-phenylpropanoic acid derivatives as PPARα/γ dual agonists

  摘要：

  The synthesis of a new series of phenylpropanoic acid derivatives incorporating an heteroaryl group at the alpha-position and their evaluation for binding and activation of PPAR alpha and PPAR gamma are presented in this report. Among the new compounds, (S)-3-{4-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-phenyl}-2-1,2,3- triazol-2-yl-propionic acid (17j), was identified as a potent human PPAR alpha/gamma dual agonist (EC50 = 0.013 and 0.061 mu M, respectively) with demonstrated oral bioavailability in rat and dog. 17j was shown to decrease insulin levels, plasma glucose, and triglycerides in the ZDF female rat model. In the human apolipoprotein A-1/CETP transgenic mouse model 17j produced increases in hApoA1 and HDL-C and decreases in plasma triglycerides. The increased potency for binding and activation of both PPAR subtypes observed with 17j when compared to previous analogs in this series was explained based on results derived from crystallographic and modeling studies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.001

文献信息

• Antidiabetic agents
  申请人：——

  公开号：US20030171377A1

  公开（公告）日：2003-09-11

  The present invention provides compounds of Formula (I): 1 wherein A, X, Q, Y, B, D, Z, and E have any of the values defined in the specification, and pharmaceutically acceptable salt thereof, that are useful as antidiabetic agents. Also disclosed are pharmaceutical compositions comprising one or more compounds of Formula I, processes for preparing compounds of Formula I, and intermediates useful for preparing compounds of Formula I.

  本发明提供了式(I)的化合物： 1 其中A、X、Q、Y、B、D、Z和E具有规范中定义的任何值，以及药用可接受的盐，这些化合物作为抗糖尿病药是有用的。还公开了包含一个或多个式I化合物的药物组合物，制备式I化合物的方法，以及用于制备式I化合物的中间体。
• Alpha substituted carboxylic acids
  申请人：Su Guo Wei

  公开号：US20050187266A1

  公开（公告）日：2005-08-25

  Alpha substituted carboxylic acids of formula (I): wherein R 1 and R 2 are as defined in the specification and R 3 is wherein Y, Ar 1 , Ar 2 , Ar 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 9a , R 10 , R 11 , R 12 , R 17 , ring A, and p are as defined in the specification; pharmaceutical compositions containing effective amounts of said compounds or their salts are useful for treating PPAR, specifically PPAR α/γ related disorders, such as diabetes, dyslipidemia, obesity and inflammatory disorders.

  式(I)的α取代羧酸，其中R1和R2如规范中定义，R3为，其中Y、Ar1、Ar2、Ar3、R4、R5、R6、R7、R8、R9、R9a、R10、R11、R12、R17、环A和p如规范中定义；含有所述化合物或其盐的有效量的药物组合物对于治疗PPAR，特别是PPAR α/γ相关疾病，如糖尿病、血脂异常、肥胖和炎症性疾病是有用的。
• Preparation of N2-alkylated 1,2,3-triazoles
  申请人：——

  公开号：US20040266848A1

  公开（公告）日：2004-12-30

  Methods and materials for preparing N2-alkylated triazoles, such as 3-{4-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-phenyl}-2-[1,2,3]triazol-2-yl-propionic acid, are disclosed. Such compounds are PPAR agonists that are useful for treating non-insulin dependent diabetes.

  揭示了用于制备N2-烷基化三唑类化合物的方法和材料，例如3-【4-【3-(5-甲基-2-苯基-噁唑-4-基)-丙基】-苯基】-2-【1,2,3】三唑-2-基丙酸。这些化合物是PPAR激动剂，可用于治疗非胰岛素依赖型糖尿病。
• Substituted acid derivatives useful as antidiabetic and antiobesity agents and method
  申请人：Cheng T. Peter

  公开号：US20070015797A1

  公开（公告）日：2007-01-18

  Compounds are provided which have the structure wherein Q is C or N, A is O or S, Z is O or a bond, X is CH or N and R 1 , R 2 , R 2a , R 2b , R 2c , R 3 , Y, x, m, and n are as defined herein, which compounds are useful as antidiabetic, hypolipidemic, and antiobesity agents.

  提供了一些化合物，它们的结构如下：其中Q为C或N，A为O或S，Z为O或键，X为CH或N，R1、R2、R2a、R2b、R2c、R3、Y、x、m和n如此定义，这些化合物可用作抗糖尿病、降脂和抗肥胖药物。
• Oral antidiabetic agents
  申请人：Warner-Lambert Company LLC

  公开号：EP1577305A1

  公开（公告）日：2005-09-21

  The present invention provides compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein:    A is    X is CH2-CH2-O or -CH2CH2CH2-;    Q is    Y is CH2;    Z is absent;    B is H;    D is H, and E is CO2H; that are useful as antidiabetic agents. Also disclosed are pharmaceutical compositions comprising compounds of formula (I).

  本发明提供了式 (I) 的化合物 或其药学上可接受的盐，其中 A 是 X是CH2- -O或- -； Q 是 Y 是 Z 不存在； B 是 H； D 是 H、 和 E 是 CO2H； 可用作抗糖尿病药物。还公开了包含式（I）化合物的药物组合物。