(R)-methyl 2-(4-bromophenoxy)-3-phenylpropanoate | 111503-67-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-methyl 2-(4-bromophenoxy)-3-phenylpropanoate
• 英文别名: Methyl 2R-2-(4-Bromophenoxy)-3-phenylpropionate；methyl (2R)-2-(4-bromophenoxy)-3-phenylpropanoate
• CAS: 111503-67-4
• 化学式: C₁₆H₁₅BrO₃
• 分子量: 335.197
• InChiKey: YZZAVXNHAMGAGS-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-(4-bromophenoxy)-3-phenylpropanoate 在 Wilkinson's catalyst 、 hydrazine hydrate 、 氢气 、 palladium diacetate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 20.0 ℃ 、405.33 kPa 条件下， 反应 44.0h， 生成 (R)-methyl 2-[4-(2-heptanoylaminoethyl)phenoxy]-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis, Characterization and Biological Evaluation of Ureidofibrate-Like Derivatives Endowed with Peroxisome Proliferator-Activated Receptor Activity

  摘要：

  A series of ureidofibrate-like derivatives was prepared and assayed for their PPAR functional activity. A calorimetric approach was used to characterize PPAR gamma-ligand interactions, and docking experiments and X-ray studies were performed to explain the observed potency and efficacy. R-1 and S-1 were selected to evaluate several aspects of their biological activity. In an adipogenic assay, both enantiomers increased the expression of PPAR gamma target genes and promoted the differentiation of 3T3-L1 fibroblasts to adipocytes. In vivo administration of these compounds to insulin resistant C57Bl/6J mice fed a high fat diet reduced visceral fat content and body weight. Examination of different metabolic parameters showed that R-1 and S-1 are insulin sensitizers. Notably, they also enhanced the expression of hepatic PPAR alpha target genes indicating that their in vivo effects stemmed from an activation of both PPAR alpha and gamma. Finally, the capability of R-1 and S-1 to inhibit cellular proliferation in colon cancer cell lines was also evaluated.

  DOI：

  10.1021/jm201306q
• 作为产物：
  描述：

  4-溴苯酚 、 L-苯基乳酸甲酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 生成 (R)-methyl 2-(4-bromophenoxy)-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis, Characterization and Biological Evaluation of Ureidofibrate-Like Derivatives Endowed with Peroxisome Proliferator-Activated Receptor Activity

  摘要：

  A series of ureidofibrate-like derivatives was prepared and assayed for their PPAR functional activity. A calorimetric approach was used to characterize PPAR gamma-ligand interactions, and docking experiments and X-ray studies were performed to explain the observed potency and efficacy. R-1 and S-1 were selected to evaluate several aspects of their biological activity. In an adipogenic assay, both enantiomers increased the expression of PPAR gamma target genes and promoted the differentiation of 3T3-L1 fibroblasts to adipocytes. In vivo administration of these compounds to insulin resistant C57Bl/6J mice fed a high fat diet reduced visceral fat content and body weight. Examination of different metabolic parameters showed that R-1 and S-1 are insulin sensitizers. Notably, they also enhanced the expression of hepatic PPAR alpha target genes indicating that their in vivo effects stemmed from an activation of both PPAR alpha and gamma. Finally, the capability of R-1 and S-1 to inhibit cellular proliferation in colon cancer cell lines was also evaluated.

  DOI：

  10.1021/jm201306q

文献信息

• Chroman- and thiochroman-4-acetic acids useful in the treatment of diabetic complications
  申请人：PFIZER INC.

  公开号：EP0230379A2

  公开（公告）日：1987-07-29

  Racemic and chiral (2R,4R)-4-c-hydroxy-2-r-(substituted) chroman (and thiochroman)-4-acetic acids and their pharmaceutically acceptable salts useful in the treatment of diabetic complications, and intermediates therefor.

  外消旋和手性(2R,4R)-4-c-羟基-2-r-(取代的)色满（和硫代色满）-4-乙酸及其用于治疗糖尿病并发症的药学上可接受的盐，以及它们的中间体。
• LIPINSKI, CHRISTOPHER A.
  作者：LIPINSKI, CHRISTOPHER A.

  DOI：——

  日期：——
• US4853410A
  申请人：——

  公开号：US4853410A

  公开（公告）日：1989-08-01
• [EN] HYDROXYACETIC ACID DERIVATIVES FOR THE TREATMENT OF DIABETIC COMPLICATIONS
  申请人：PFIZER INC.

  公开号：WO1987004344A1

  公开（公告）日：1987-07-30

  (EN) Racemic and chiral (2R, 4R)-4-c-hydroxy-2-r-(substituted)chroman(and thiochroman)-4-acetic acids and their pharmaceutically acceptable salts, their use in the treatment of diabetic complications and intermediates therefor.(FR) Acides (2R, 4R)-4-c-hydroxy-2-r-(substitué)chroman(et thiochroman)-4-acétique racémique et chiral, et leurs sels pharmaceutiquement acceptables, leurs intermédiaires, et leur utilisation dans le traitement de complications diabétiques.
• Synthesis, Characterization and Biological Evaluation of Ureidofibrate-Like Derivatives Endowed with Peroxisome Proliferator-Activated Receptor Activity
  作者：L. Porcelli、F. Gilardi、A. Laghezza、L. Piemontese、N. Mitro、A. Azzariti、F. Altieri、L. Cervoni、G. Fracchiolla、M. Giudici、U. Guerrini、A. Lavecchia、R. Montanari、C. Di Giovanni、A. Paradiso、G. Pochetti、G. M. Simone、P. Tortorella、M. Crestani、F. Loiodice

  DOI：10.1021/jm201306q

  日期：2012.1.12

  A series of ureidofibrate-like derivatives was prepared and assayed for their PPAR functional activity. A calorimetric approach was used to characterize PPAR gamma-ligand interactions, and docking experiments and X-ray studies were performed to explain the observed potency and efficacy. R-1 and S-1 were selected to evaluate several aspects of their biological activity. In an adipogenic assay, both enantiomers increased the expression of PPAR gamma target genes and promoted the differentiation of 3T3-L1 fibroblasts to adipocytes. In vivo administration of these compounds to insulin resistant C57Bl/6J mice fed a high fat diet reduced visceral fat content and body weight. Examination of different metabolic parameters showed that R-1 and S-1 are insulin sensitizers. Notably, they also enhanced the expression of hepatic PPAR alpha target genes indicating that their in vivo effects stemmed from an activation of both PPAR alpha and gamma. Finally, the capability of R-1 and S-1 to inhibit cellular proliferation in colon cancer cell lines was also evaluated.