3-hydroxy-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester | 863902-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 3-hydroxy-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester
• 英文别名: methyl 3-hydroxy-6-methylthieno[2,3-b]pyridine-2-carboxylate
• CAS: 863902-67-4
• 化学式: C₁₀H₉NO₃S
• 分子量: 223.252
• InChiKey: LDOWMUHSQFXDPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  347.6±37.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 生成 3-Hydroxy-6-methylthieno[2,3-b]pyridine-2-carboxylic acid
  参考文献：
  名称：

  Efficient synthesis and 5-LOX/COX-inhibitory activity of some 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives

  摘要：

  A series of 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives has been prepared and subsequently evaluated with regards to the inhibition of 5-LOX/COX. Structure optimization furnished derivatives with promising in vitro activity as dual 5-LOX/COX inhibitors with submicromolar IC50 values for inhibition of 5-LOX and COX-1, respectively. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.012
• 作为产物：
  描述：

  4-氯-6-甲基烟酸甲酯 在 sodium methylate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 1.08h， 以29%的产率得到3-hydroxy-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Inhibitors of protein tyrosine phosphatase 1B

  摘要：

  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。

  公开号：

  US20050203081A1

文献信息

• 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.
• Efficient synthesis and 5-LOX/COX-inhibitory activity of some 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives
  作者：Finn K. Hansen、Mehdi Khankischpur、Ibrahim Tolaymat、Renata Mesaros、Gerd Dannhardt、Detlef Geffken

  DOI：10.1016/j.bmcl.2012.06.012

  日期：2012.8

  A series of 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives has been prepared and subsequently evaluated with regards to the inhibition of 5-LOX/COX. Structure optimization furnished derivatives with promising in vitro activity as dual 5-LOX/COX inhibitors with submicromolar IC50 values for inhibition of 5-LOX and COX-1, respectively. (c) 2012 Elsevier Ltd. All rights reserved.
• 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。