[3-Hydroxy-4-[hydroxy(propan-2-yl)carbamoyl]-2,6-dipropylphenyl] acetate | 279215-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: [3-Hydroxy-4-[hydroxy(propan-2-yl)carbamoyl]-2,6-dipropylphenyl] acetate
• CAS: 279215-25-7
• 化学式: C₁₈H₂₇NO₅
• 分子量: 337.416
• InChiKey: CVJRVGDFBZGIAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [3-Hydroxy-4-[hydroxy(propan-2-yl)carbamoyl]-2,6-dipropylphenyl] acetate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以92%的产率得到Acetic acid 2-isopropyl-3-oxo-5,7-dipropyl-2,3-dihydro-benzo[d]isoxazol-6-yl ester
  参考文献：
  名称：

  N-取代的1,2-苯并恶唑啉-3-酮的第一个一般合成

  摘要：

  已经开发了标题化合物的方便合成。关键的合成步骤包括：（1）将易得的水杨酸衍生物转化为相应的N-取代的水杨基异羟肟酸；（2）在Mitsunobu条件下环化异羟肟酸，得到标题化合物。

  DOI：

  10.1016/s0040-4039(00)00164-7
• 作为产物：
  描述：

  methyl 2,4-bis(allyloxy)benzoate 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 31.5h， 生成 [3-Hydroxy-4-[hydroxy(propan-2-yl)carbamoyl]-2,6-dipropylphenyl] acetate
  参考文献：
  名称：

  Design and Synthesis of α-Aryloxyphenylacetic Acid Derivatives:  A Novel Class of PPARα/γ Dual Agonists with Potent Antihyperglycemic and Lipid Modulating Activity

  摘要：

  The synthesis and structure-activity relationships of novel series of alpha-aryloxyphenylacetic acids as PPARalpha/gamma dual agonists are reported. The initial search for surrogates of the ester group in the screen lead led first to the optimization of a subseries with a ketone moiety. Further efforts to modify the ketone subseries led to the design and synthesis of two new subseries containing fused heterocyclic ring systems. All these analogues were characterized by their "super" PPARalpha agonist activity and weak or partial agonist activity on PPARgamma in PPAR-GAL4 transactivation assays despite their similar binding affinities for both receptors. The cocrystal structures of compounds 7 and rosiglitazone with PPARgamma-LBD were compared, and significant differences were found in their interactions with the receptor. Select analogues in each subseries were further evaluated for in vivo efficacy. They all showed excellent anti-hyperglycemic efficacy in a db/db mouse model and hypolipidemic activity in hamster and dog models without provoking the typical PPARgamma-associated side effects in the rat tolerability assay.

  DOI：

  10.1021/jm0502135

文献信息

• US7495020B2
  申请人：——

  公开号：US7495020B2

  公开（公告）日：2009-02-24