ethyl 4-amino-5-(3-((1E)-3-hydroxyprop-1-enyl)phenyl)isoxazole-3-carboxylate | 745079-16-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: ethyl 4-amino-5-(3-((1E)-3-hydroxyprop-1-enyl)phenyl)isoxazole-3-carboxylate
• 英文别名: ethyl 4-amino-5-[3-[(E)-3-hydroxyprop-1-enyl]phenyl]-1,2-oxazole-3-carboxylate
• CAS: 745079-16-7
• 化学式: C₁₅H₁₆N₂O₄
• 分子量: 288.303
• InChiKey: ARJXPWYVRDPBSZ-GQCTYLIASA-N

物化性质

• 沸点：
  536.2±50.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  98.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-amino-5-(3-((1E)-3-hydroxyprop-1-enyl)phenyl)isoxazole-3-carboxylate 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 4-amino-5-(3-((1E)-3-(3-hydroxy-2-(methoxycarbonyl)phenoxy)prop-1-enyl)phenyl)isoxazole-3-carboxylic acid
  参考文献：
  名称：

  Isoxazole carboxylic acids as protein tyrosine phosphatase 1B (PTP1B) inhibitors

  摘要：

  Guided by X-ray crystallography, we have extended the structure-activity relationship (SAR) study on an isoxazole carboxylic acid-based PTP1B inhibitor (1) and more potent and equally selective (>20-fold selectivity over the highly homologous T-cell PTPase, TCPTP) PTP1B inhibitors were identified. Inhibitor 7 demonstrated good cellular activity against PTP1B in COS 7 cells.

  DOI：

  10.1016/j.bmcl.2004.08.063
• 作为产物：
  描述：

  1-(3-iodo-phenyl)-2-nitro-ethanone 在 copper(l) iodide 、 tris(dibenzylideneacetone)dipalladium (0) 、 三(2-呋喃基)膦 、 铁粉 、 氯化铵 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 4-amino-5-(3-((1E)-3-hydroxyprop-1-enyl)phenyl)isoxazole-3-carboxylate
  参考文献：
  名称：

  Isoxazole carboxylic acids as protein tyrosine phosphatase 1B (PTP1B) inhibitors

  摘要：

  Guided by X-ray crystallography, we have extended the structure-activity relationship (SAR) study on an isoxazole carboxylic acid-based PTP1B inhibitor (1) and more potent and equally selective (>20-fold selectivity over the highly homologous T-cell PTPase, TCPTP) PTP1B inhibitors were identified. Inhibitor 7 demonstrated good cellular activity against PTP1B in COS 7 cells.

  DOI：

  10.1016/j.bmcl.2004.08.063

文献信息

• Protein-tyrosine phosphatase inhibitors and uses thereof
  申请人：——

  公开号：US20040214870A1

  公开（公告）日：2004-10-28

  The present invention is directed to compounds of formula (I), 1 or a pharmaceutically suitable salt or prodrug thereof, which are useful for the selective inhibition of protein tyrosine phosphatase-1B (PTP1B), and are useful for the treatment of disorders caused by overexpressed or altered protein tyrosine phosphatase 1B.

  本发明涉及式(I)的化合物，或其药用适宜盐或前药，用于选择性抑制蛋白酪氨酸磷酸酶-1B（PTP1B），并且用于治疗由过度表达或改变的蛋白酪氨酸磷酸酶1B引起的疾病。
• US7169797B2
  申请人：——

  公开号：US7169797B2

  公开（公告）日：2007-01-30
• Isoxazole carboxylic acids as protein tyrosine phosphatase 1B (PTP1B) inhibitors
  作者：Hongyu Zhao、Gang Liu、Zhili Xin、Michael D. Serby、Zhonghua Pei、Bruce G. Szczepankiewicz、Philip J. Hajduk、Cele Abad-Zapatero、Charles W. Hutchins、Thomas H. Lubben、Stephen J. Ballaron、Deanna L. Haasch、Wiweka Kaszubska、Cristina M. Rondinone、James M. Trevillyan、Michael R. Jirousek

  DOI：10.1016/j.bmcl.2004.08.063

  日期：2004.11

  Guided by X-ray crystallography, we have extended the structure-activity relationship (SAR) study on an isoxazole carboxylic acid-based PTP1B inhibitor (1) and more potent and equally selective (>20-fold selectivity over the highly homologous T-cell PTPase, TCPTP) PTP1B inhibitors were identified. Inhibitor 7 demonstrated good cellular activity against PTP1B in COS 7 cells.