2-Methyl-7-oxo-4,7-dihydro-thieno[3,2-b]pyridine-3,5-dicarboxylic acid 3-methyl ester | 169831-69-0

• 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: 2-Methyl-7-oxo-4,7-dihydro-thieno[3,2-b]pyridine-3,5-dicarboxylic acid 3-methyl ester
• 英文别名: 3-methoxycarbonyl-2-methyl-7-oxo-4H-thieno[3,2-b]pyridine-5-carboxylic acid
• CAS: 169831-69-0
• 化学式: C₁₁H₉NO₅S
• 分子量: 267.262
• InChiKey: SMNJDGDWHFJSQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-氨基四氮唑 、 2-Methyl-7-oxo-4,7-dihydro-thieno[3,2-b]pyridine-3,5-dicarboxylic acid 3-methyl ester 在 N,N'-羰基二咪唑 作用下， 生成 4,7-dihydro-2-methyl-7-oxo-5-<(1H-tetrazol-5-ylamino)carbonyl>thieno<3,2-b>pyridine-3-carboxylic acid, methyl ester
  参考文献：
  名称：

  Kynurenic Acid Derivatives Inhibit the Binding of Nerve Growth Factor (NGF) to the Low-Affinity p75 NGF Receptor

  摘要：

  The ability of a series of substituted kynurenic acids, thienopyridinonecarboxylic acids, and related compounds to inhibit the binding of nerve growth factor (NGF) to the p75 NGF receptor (NGFR) was evaluated in a radioligand binding assay that utilized a biotinylated derivative of the extracellular domain of p75 NGFR (p75(ext)) fixed to streptavidin-coated plastic wells. Two compounds, 6-aminokynurenic acid (5h) and the 3-methyl ester of 4,7-dihydro-2-methyl-7-oxo-thieno[3,2-b]pyridine-3,5-dicarboxylic acid (16), were found to inhibit the binding of [I-125]NGF to p75(ext) with IC50 values in the low micromolar range. Other amino-substituted kynurenic acids also possessed activity at slightly higher concentrations. Several structural features seem to be essential, including the carboxylic acid, a polar group on the benzene ring (or thiophene ring, in the case of analogues of 16), and the C-4 carbonyl group in the pyridinone ring. These compounds were also found to inhibit the binding of [I-125]NGF to its receptors in membranes from PC12 cells (which express p75 as well as trk(a) receptors for NGF) and DG44-CHO cells (transfected with full length p75 NGFR). The available data for 5h and 16 do not allow the determination of whether the effects of these compounds are mediated by their interaction with NGF or the NGF receptors.

  DOI：

  10.1021/jm00022a008
• 作为产物：
  描述：

  4-氨基-2-甲基噻吩-3-甲酸甲酯 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.08h， 生成 2-Methyl-7-oxo-4,7-dihydro-thieno[3,2-b]pyridine-3,5-dicarboxylic acid 3-methyl ester
  参考文献：
  名称：

  Kynurenic Acid Derivatives Inhibit the Binding of Nerve Growth Factor (NGF) to the Low-Affinity p75 NGF Receptor

  摘要：

  The ability of a series of substituted kynurenic acids, thienopyridinonecarboxylic acids, and related compounds to inhibit the binding of nerve growth factor (NGF) to the p75 NGF receptor (NGFR) was evaluated in a radioligand binding assay that utilized a biotinylated derivative of the extracellular domain of p75 NGFR (p75(ext)) fixed to streptavidin-coated plastic wells. Two compounds, 6-aminokynurenic acid (5h) and the 3-methyl ester of 4,7-dihydro-2-methyl-7-oxo-thieno[3,2-b]pyridine-3,5-dicarboxylic acid (16), were found to inhibit the binding of [I-125]NGF to p75(ext) with IC50 values in the low micromolar range. Other amino-substituted kynurenic acids also possessed activity at slightly higher concentrations. Several structural features seem to be essential, including the carboxylic acid, a polar group on the benzene ring (or thiophene ring, in the case of analogues of 16), and the C-4 carbonyl group in the pyridinone ring. These compounds were also found to inhibit the binding of [I-125]NGF to its receptors in membranes from PC12 cells (which express p75 as well as trk(a) receptors for NGF) and DG44-CHO cells (transfected with full length p75 NGFR). The available data for 5h and 16 do not allow the determination of whether the effects of these compounds are mediated by their interaction with NGF or the NGF receptors.

  DOI：

  10.1021/jm00022a008

文献信息

• Kynurenic Acid Derivatives Inhibit the Binding of Nerve Growth Factor (NGF) to the Low-Affinity p75 NGF Receptor
  作者：Juan C. Jaen、Edgardo Laborde、Ruth A. Bucsh、Bradley W. Caprathe、Roderick J. Sorenson、James Fergus、Katharyn Spiegel、James Marks、Melvin R. Dickerson、Robert E. Davis

  DOI：10.1021/jm00022a008

  日期：1995.10

  The ability of a series of substituted kynurenic acids, thienopyridinonecarboxylic acids, and related compounds to inhibit the binding of nerve growth factor (NGF) to the p75 NGF receptor (NGFR) was evaluated in a radioligand binding assay that utilized a biotinylated derivative of the extracellular domain of p75 NGFR (p75(ext)) fixed to streptavidin-coated plastic wells. Two compounds, 6-aminokynurenic acid (5h) and the 3-methyl ester of 4,7-dihydro-2-methyl-7-oxo-thieno[3,2-b]pyridine-3,5-dicarboxylic acid (16), were found to inhibit the binding of [I-125]NGF to p75(ext) with IC50 values in the low micromolar range. Other amino-substituted kynurenic acids also possessed activity at slightly higher concentrations. Several structural features seem to be essential, including the carboxylic acid, a polar group on the benzene ring (or thiophene ring, in the case of analogues of 16), and the C-4 carbonyl group in the pyridinone ring. These compounds were also found to inhibit the binding of [I-125]NGF to its receptors in membranes from PC12 cells (which express p75 as well as trk(a) receptors for NGF) and DG44-CHO cells (transfected with full length p75 NGFR). The available data for 5h and 16 do not allow the determination of whether the effects of these compounds are mediated by their interaction with NGF or the NGF receptors.