3-(2-methoxy-2-oxoethoxy)-2-(methoxycarbonyl)benzo[b]thiophene-6-carboxylic acid | 863905-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-(2-methoxy-2-oxoethoxy)-2-(methoxycarbonyl)benzo[b]thiophene-6-carboxylic acid
• 英文别名: 3-methoxycarbonylmethoxy-benzo[b]thiophene-2,6-dicarboxylic acid 2-methyl ester；3-Methoxycarbonylmethoxy-benzo-[b]thiophene-2,6-dicarboxylic acid 2-methyl ester；2-methoxycarbonyl-3-(2-methoxy-2-oxoethoxy)-1-benzothiophene-6-carboxylic acid
• CAS: 863905-58-2
• 化学式: C₁₄H₁₂O₇S
• 分子量: 324.311
• InChiKey: MWQXPJPAFZANEY-UHFFFAOYSA-N

物化性质

• 沸点：
  525.0±45.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(2-methoxy-2-oxoethoxy)-2-(methoxycarbonyl)benzo[b]thiophene-6-carboxylic acid 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 3-methoxycarbonylmethoxy-6-(5-methyl-1-phenyl-1H-pyrazol-3-ylcarbamoyl)benzo[b]thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Bicyclic and tricyclic thiophenes as protein tyrosine phosphatase 1B inhibitors

  摘要：

  A novel pyridothiophene inhibitor of PTP1B was discovered by rational screening of phosphotyrosine mimics at high micromolar concentrations. The potency of this lead compound has been improved significantly by medicinal chemistry guided by X-ray crystallography and molecular modeling. Excellent consistency has been observed between structure-activity relationships and structural information from PTP1B-inhibitor complexes.

  DOI：

  10.1016/j.bmc.2005.11.005
• 作为产物：
  描述：

  2-硝基对苯二酸单甲酯 在 lithium hydroxide 、 硫酸 、 potassium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 3-(2-methoxy-2-oxoethoxy)-2-(methoxycarbonyl)benzo[b]thiophene-6-carboxylic acid
  参考文献：
  名称：

  Bicyclic and tricyclic thiophenes as protein tyrosine phosphatase 1B inhibitors

  摘要：

  A novel pyridothiophene inhibitor of PTP1B was discovered by rational screening of phosphotyrosine mimics at high micromolar concentrations. The potency of this lead compound has been improved significantly by medicinal chemistry guided by X-ray crystallography and molecular modeling. Excellent consistency has been observed between structure-activity relationships and structural information from PTP1B-inhibitor complexes.

  DOI：

  10.1016/j.bmc.2005.11.005

文献信息

• Inhibitors of protein tyrosine phosphatase 1B
  申请人：Lee Jinbo

  公开号：US20050203081A1

  公开（公告）日：2005-09-15

  Protein tyrosine phosphatases (PTPases) such as PTP1B can play a role in regulating a wide variety of cellular responses such as insulin signaling. Substituted bicyclic fused-thiophene compounds can inhibit PTP1B and thereby induce greater insulin sensitivity. Accordingly, PTP1B inhibition can provide an alternate treatment for PTPase-mediated disorders such as diabetes.

  蛋白质酪氨酸磷酸酶（PTPases），如PTP1B，在调节广泛的细胞反应，如胰岛素信号传导中发挥作用。取代的并环融合噻吩化合物可以抑制PTP1B，从而增加胰岛素敏感性。因此，PTP1B的抑制可以提供一种治疗PTPase介导的疾病，如糖尿病的替代方法。
• Inhibitors of Protein Tyrosine Phosphatase 1B
  申请人：Lee Jinbo

  公开号：US20090048286A1

  公开（公告）日：2009-02-19

  Protein tyrosine phosphatases (PTPases) such as PTP1B can play a role in regulating a wide variety of cellular responses such as insulin signaling. Substituted bicyclic fused-thiophene compounds can inhibit PTP1B and thereby induce greater insulin sensitivity. Accordingly, PTP1B inhibition can provide an alternate treatment for PTPase-mediated disorders such as diabetes.

  蛋白酪氨酸磷酸酶（PTPases）如PTP1B可以在调节各种细胞响应（如胰岛素信号传导）方面发挥作用。取代的双环融合噻吩化合物可以抑制PTP1B，从而增强胰岛素敏感性。因此，PTP1B的抑制可以提供PTPase介导的疾病（如糖尿病）的另一种治疗方法。
• [EN] INHIBITORS OF PROTEIN TYROSINE PHOSPHATASE 1B<br/>[FR] INHIBITEURS DE LA PROTEINE TYROSINE PHOSPHATASE 1B
  申请人：WYETH CORP

  公开号：WO2005081960A2

  公开（公告）日：2005-09-09

  Protein tyrosine phosphatases (PTPases) such as PTP1B can play a role in regulating a wide variety of cellular responses such as insulin signaling. Substituted bicyclic fused-thiophene compounds can inhibit PTP1B and thereby induce greater insulin sensitivity. Accordingly, PTP1B inhibition can provide an alternate treatment for PTPase-mediated disorders such as diabetes.
• Bicyclic and tricyclic thiophenes as protein tyrosine phosphatase 1B inhibitors
  作者：A.F. Moretto、S.J. Kirincich、W.X. Xu、M.J. Smith、Z.-K. Wan、D.P. Wilson、B.C. Follows、E. Binnun、D. Joseph-McCarthy、K. Foreman、D.V. Erbe、Y.L. Zhang、S.K. Tam、S.Y. Tam、J. Lee

  DOI：10.1016/j.bmc.2005.11.005

  日期：2006.4

  A novel pyridothiophene inhibitor of PTP1B was discovered by rational screening of phosphotyrosine mimics at high micromolar concentrations. The potency of this lead compound has been improved significantly by medicinal chemistry guided by X-ray crystallography and molecular modeling. Excellent consistency has been observed between structure-activity relationships and structural information from PTP1B-inhibitor complexes.