7-nitro-4-hydroxy-2-methoxycarbonylquinoline | 16133-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-nitro-4-hydroxy-2-methoxycarbonylquinoline
• 英文别名: methyl 7-nitro-4-oxo-1H-quinoline-2-carboxylate
• CAS: 16133-45-2
• 化学式: C₁₁H₈N₂O₅
• 分子量: 248.195
• InChiKey: DGNJPSYPDOPQQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-nitro-4-hydroxy-2-methoxycarbonylquinoline 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 sodium hydroxide 、 氘 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 10.5h， 生成 <4-2H>-7-aminoquinoline-2-carboxylic acid
  参考文献：
  名称：

  Streptonigrin biosynthesis. 8. Evidence for the involvement of a new shikimate pathway product and a new route to quinolines

  摘要：

  DOI：

  10.1021/ja00236a071
• 作为产物：
  描述：

  dimethyl 2-(3-nitrophenylamino)but-2-endioate 以 二苯醚 为溶剂， 以48 %的产率得到7-nitro-4-hydroxy-2-methoxycarbonylquinoline
  参考文献：
  名称：

  结合局部构象偏好和螺旋芳香低聚酰胺折叠体的疏溶剂效应

  摘要：

  芳香族低聚酰胺折叠体是使用新开发的单体设计的，因此局部构象偏好和疏溶剂效应都促进了螺旋折叠。固相合成提供了对所需序列的快速访问。NMR 和紫外吸收光谱都证明了取决于序列长度的急剧溶剂驱动的构象转变。

  DOI：

  10.1039/d3ob00473b

文献信息

• Platelet adenosine diphosphate receptor antagonists
  申请人：Schering Aktiengesellschaft

  公开号：US20030060474A1

  公开（公告）日：2003-03-27

  Compounds of the following formula (I): 1 where a, b, R 1 , R 2 , R 4 and R 6 are described herein, are useful as inhibitors of platelet adenosine diphosphate. Pharmaceutical compositions containing these compounds, methods of using these compounds as antithrombotic agents and processes for synthesizing these compounds are also described herein.

  以下公式（I）的化合物：其中a、b、R1、R2、R4和R6如下所述，可用作抑制血小板腺苷二磷酸的药物。本文还描述了含有这些化合物的药物组合物，使用这些化合物作为抗血栓药物的方法以及合成这些化合物的过程。
• Stover, James S.; Shi, Jin; Jin, Wei, Journal of the American Chemical Society, 2009, vol. 131, p. 3342 - 3348
  作者：Stover, James S.、Shi, Jin、Jin, Wei、Vogt, Peter K.、Boger, Dale L.

  DOI：——

  日期：——
• 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.
• 2-AMINOCARBONYL-QUINOLINE COMPOUNDS AS PLATELET ADENOSINE DIPHOSPHATE RECEPTOR ANTAGONISTS
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP1578423B1

  公开（公告）日：2010-08-18
• US6861424B2
  申请人：——

  公开号：US6861424B2

  公开（公告）日：2005-03-01