5-[3-(3-hydroxy-propenyl)-phenyl]-isoxazole-3-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 5-[3-(3-hydroxy-propenyl)-phenyl]-isoxazole-3-carboxylic acid methyl ester
• 英文别名: methyl 5-[3-[(E)-3-hydroxyprop-1-enyl]phenyl]-1,2-oxazole-3-carboxylate
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: AUKWPTLLRLOXFL-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[3-(3-hydroxy-propenyl)-phenyl]-isoxazole-3-carboxylic acid methyl ester 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 5-(3-((1E)-3-(3-hydroxy-2-(methoxycarbonyl)phenoxy)prop-1-enyl)phenyl)isoxazole-3-carboxylic acid
  参考文献：
  名称：

  Fragment Screening and Assembly:  A Highly Efficient Approach to a Selective and Cell Active Protein Tyrosine Phosphatase 1B Inhibitor

  摘要：

  Using an NMR-based fragment screening and X-ray crystal structure-based assembly, starting with millimolar ligands for both the catalytic site and the second phosphotyrosine binding site, we have identified a small-molecule inhibitor of protein tyrosine phosphatase 1B with low micromolar inhibition constant, high selectivity (30-fold) over the highly homologous T-cell protein tyrosine phosphatase, and good cellular activity in COS-7 cells.

  DOI：

  10.1021/jm034122o
• 作为产物：
  描述：

  3-碘苯乙酮 在 甲醇 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 copper(l) iodide 、 三(2-呋喃基)膦 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 92.0h， 生成 5-[3-(3-hydroxy-propenyl)-phenyl]-isoxazole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Fragment Screening and Assembly:  A Highly Efficient Approach to a Selective and Cell Active Protein Tyrosine Phosphatase 1B Inhibitor

  摘要：

  Using an NMR-based fragment screening and X-ray crystal structure-based assembly, starting with millimolar ligands for both the catalytic site and the second phosphotyrosine binding site, we have identified a small-molecule inhibitor of protein tyrosine phosphatase 1B with low micromolar inhibition constant, high selectivity (30-fold) over the highly homologous T-cell protein tyrosine phosphatase, and good cellular activity in COS-7 cells.

  DOI：

  10.1021/jm034122o

文献信息

• Fragment Screening and Assembly:  A Highly Efficient Approach to a Selective and Cell Active Protein Tyrosine Phosphatase 1B Inhibitor
  作者：Gang Liu、Zhili Xin、Zhonghua Pei、Philip J. Hajduk、Cele Abad-Zapatero、Charles W. Hutchins、Hongyu Zhao、Thomas H. Lubben、Stephen J. Ballaron、Deanna L. Haasch、Wiweka Kaszubska、Cristina M. Rondinone、James M. Trevillyan、Michael R. Jirousek

  DOI：10.1021/jm034122o

  日期：2003.9.1

  Using an NMR-based fragment screening and X-ray crystal structure-based assembly, starting with millimolar ligands for both the catalytic site and the second phosphotyrosine binding site, we have identified a small-molecule inhibitor of protein tyrosine phosphatase 1B with low micromolar inhibition constant, high selectivity (30-fold) over the highly homologous T-cell protein tyrosine phosphatase, and good cellular activity in COS-7 cells.