6-氨基-1,4-二氢-4-氧代-2-喹啉羧酸甲酯 | 52979-42-7

• 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
• 中文名称: 6-氨基-1,4-二氢-4-氧代-2-喹啉羧酸甲酯
• 英文名称: methyl 6-amino-1,4-dihydro-4-oxo-2-quinolinecarboxylate
• 英文别名: 6-amino-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid methyl ester；Methyl 6-amino-4-hydroxyquinoline-2-carboxylate；methyl 6-amino-4-oxo-1H-quinoline-2-carboxylate
• CAS: 52979-42-7
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: LTCKDZAUNSZESX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 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：
  81.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-氨基-1,4-二氢-4-氧代-2-喹啉羧酸甲酯 在 lithium hydroxide monohydrate 作用下， 以 甲醇 为溶剂， 生成 6-氨基-4-羟基-2-喹啉羧酸
  参考文献：
  名称：

  [EN] ANTIBODIES AGAINST SEROTONIN, TRYPTOPHAN AND KYNURENINE METABOLITES AND USES THEREOF
  [FR] ANTICORPS DIRIGÉS CONTRE DES MÉTABOLITES DE SÉROTONINE, DE TRYPTOPHANE ET DE KYNURÉNINE ET LEURS UTILISATIONS

  摘要：

  本发明提供了抗体和制备抗体的方法，用于代谢物在血清素、色氨酸和酮喹酮途径中，如5-羟基吲哚-3-乙酸（5-HIAA）、褪黑激素（MT）和喹酮酸（KYNA）。特定的代谢物抗体对结构相关的代谢物具有低的交叉反应性，并且是用于特定和敏感免疫测定的有用试剂。本发明还提供了使用这些抗体来测量人类患者生物样本中5-HIAA、褪黑激素或喹酮酸水平的方法。

  公开号：

  WO2016079708A1
• 作为产物：
  描述：

  2-((4-硝基苯基)氨基)-2-丁烯二酸二甲酯 在 镍 氢气 作用下， 以 甲醇 为溶剂， 25.0~240.0 ℃ 、344.73 kPa 条件下， 反应 1.58h， 生成 6-氨基-1,4-二氢-4-氧代-2-喹啉羧酸甲酯
  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

• [EN] 2-AMINOCARBONYL-QUINOLINE COMPOUNDS AS PLATELET ADENOSINE DIPHOSPHATE RECEPTOR ANTAGONISTS<br/>[FR] COMPOSES DE 2-AMINOCARBONYL-QUINOLINE UTILISES EN TANT QU'ANTAGONISTES DU RECEPTEUR DE L'ADENOSINE DIPHOSPHATE DES PLAQUETTES
  申请人：SCHERING AG

  公开号：WO2004052366A1

  公开（公告）日：2004-06-24

  Compounds of formula (I), where m, n, R1, R2, R3, R4 and R6 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.

  式（I）中的化合物，其中m、n、R1、R2、R3、R4和R6如本文所述，可用作血小板腺苷二磷酸酶抑制剂。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剂的方法以及合成这些化合物的方法。
• 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。
• PATHWAY SPECIFIC ASSAYS FOR PREDICTING IRRITABLE BOWEL SYNDROME DIAGNOSIS
  申请人：NESTEC S.A.

  公开号：US20160130279A1

  公开（公告）日：2016-05-12

  The present invention provides antibodies and methods for preparing antibodies to metabolites in the serotonin, tryptophan, kynurenine pathways. The prepared antibodies have low cross-reactivity to related metabolites, and are useful reagents for specific and sensitive immunoassays The present invention also provides stable derivatives of various metabolites and short chain fatty acids. The derivative can be conjugated to a biomolecule such as a carrier protein and combined with an adjuvant to stimulate an immune response. The derivatives can also be conjugated to other biomolecules.

  本发明提供了抗体及其制备方法，用于检测血清素、色氨酸、酪氨酸代谢途径中的代谢产物。所制备的抗体对相关代谢产物的交叉反应较低，可用作特异性和敏感性免疫测定的有用试剂。本发明还提供各种代谢产物和短链脂肪酸的稳定衍生物。这些衍生物可与载体蛋白等生物分子结合，并与佐剂结合以刺激免疫反应。这些衍生物也可与其他生物分子结合。
• [EN] PATHWAY SPECIFIC ASSAYS FOR PREDICTING IRRITABLE BOWEL SYNDROME DIAGNOSIS<br/>[FR] DOSAGES SPÉCIFIQUES DES VOIES DE SIGNALISATION POUR LA PRÉDICTION DE DIAGNOSTIC DU SYNDROME DU CÔLON IRRITABLE
  申请人：NESTEC SA

  公开号：WO2014188377A3

  公开（公告）日：2015-03-05
• Novel vitexin-inspired scaffold against leukemia
  作者：Taotao Ling、Walter Lang、Xiang Feng、Sourav Das、Julie Maier、Cynthia Jeffries、Anang Shelat、Fatima Rivas

  DOI：10.1016/j.ejmech.2018.01.004

  日期：2018.2

  Acute lymphoblastic leukemia (ALL) is the most common type of leukemia in children. Up to a quarter of ALL patients relapse and face poor prognosis. To identify new compound leads, we conducted a phenotypic screen using terrestrial natural product (NP) fractions against immortalized ALL cellular models.We identified vitexin, a flavonoid, as a promising hit with biological activity (EC50 = 30 mu M) in pre-B cell ALL models with no toxicity against normal human tissue (BJ cells) at the tested concentrations. To develop more potent compounds against ALL and elucidate its potential mode of action, a vitexin-inspired compound library was synthesized. Thus, we developed an improved and scalable protocol for the direct synthesis of 4-quinolone core heterocycles containing an N-sulfonamide using a one-pot condensation reaction protocol. The newly generated compounds represent a novel molecular scaffold against ALL as exemplified by compounds 13 and 15, which demonstrated EC50 values in the low micromolar range (0.3-10 mu M) with little to no toxicity in normal cellular models. Computational studies support the hypothesis that these compounds are potential CDK inhibitors. The compounds induced apoptosis, caused cell arrest at G0/G1 and G2/M, and induced ROS in cancer cells. (C) 2018 Elsevier Masson SAS. All rights reserved.