4-benzyloxyquinoline-2-carboxylic acid | 52144-34-0

• 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: 4-benzyloxyquinoline-2-carboxylic acid
• 英文别名: kynurenic acid benzyl ether；4-Benzyloxy-chinolin-2-carbonsaeure；2-carboxy-4-benzyloxyquinoline；4-Benzyloxyquinaldic acid；4-phenylmethoxyquinoline-2-carboxylic acid
• CAS: 52144-34-0
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: NFANKIOZMXAOQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-benzyloxyquinoline-2-carboxylic acid 在 palladium on activated charcoal 、 氨 作用下， 生成 犬尿喹酸
  参考文献：
  名称：

  Nakayama, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1950, vol. 70, p. 423

  摘要：

  DOI：
• 作为产物：
  描述：

  犬尿喹酸 在 sodium hydroxide 、 硫酸 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 4-benzyloxyquinoline-2-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation on HRPE cells of ascorbic and 6-bromoascorbic acid conjugates with neuroactive molecules

  摘要：

  Preliminary investigations allowed us to anticipate that conjugation of nipecotic acid with L-ascorbate (AA) gave a prodrug endowed with anticonvulsant activity in mice. In view of these results, and in order to get deepen insight into the molecular aspects at the base of the transport mechanism, a second generation of compounds, based on 6-bromo-6-deoxy-L-ascorbic acid (BrAA) as the carrier molecule was designed and synthesized. Effects of the chirality of the transported drug was also investigated on R- and S-nipecotic acid. Interaction and uptake modalities were evaluated in our in vitro model based on human retinal pigment epithelium cells (HRPE), which expresses the membrane L-ascorbic acid (AA) SVCT2 transporters. A remarkable increase on SVCT2 affinity was found going from AA to BrAA conjugates, that is, 11 (K-i = 1187 +/- 78 muM) versus 19 (K-i = 193 +/- 14 muM) and 12 (K-i = 39.8 +/- 3.2 muM) versus 20, (K-i = 7.4 +/- 0.8 muM). Taken together, these data are in agreement with our initial hypothesis on the possibility to achieve better affinities by conjugation with AA analogs, and also consent to hypothesize the presence of accessory interactions that may improve transporters recognition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.043

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：Bryant Judi

  公开号：US20060122188A1

  公开（公告）日：2006-06-08

  Compounds of the following formula: where m, n, R 1 , R 2 , R 3 , 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.

  以下公式所描述的化合物：其中m，n，R1，R2，R3，R4和R6，在抑制血小板腺苷二磷酸方面具有用途。本文还描述了含有这些化合物的药物组成物，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。
• Ames et al., Journal of the Chemical Society, 1956, p. 3079,3082
  作者：Ames et al.

  DOI：——

  日期：——
• Design, Synthesis and Activity of Ascorbic Acid Prodrugs of Nipecotic, Kynurenic and Diclophenamic Acids, Liable to Increase Neurotropic Activity
  作者：Stefano Manfredini、Barbara Pavan、Silvia Vertuani、Martina Scaglianti、Donatello Compagnone、Carla Biondi、Angelo Scatturin、Sergio Tanganelli、Luca Ferraro、Puttur Prasad、Alessandro Dalpiaz

  DOI：10.1021/jm015556r

  日期：2002.1.1

  To improve the entry of certain drugs into brain, ascorbic acid (AA) conjugates of these drugs were synthesized and their capacity to interact with SVCT2 ascorbate transporters was explored. Kinetic studies clearly indicate that all of the conjugates were able to competitively inhibit ascorbate transport in human retinal pigment epithelial cells (HRPE). In vivo studies, in a mouse model system, demonstrate that conjugate 3 is better absorbed compared to the nonconjugated parent drug.
• 2-AMINOCARBONYL-QUINOLINE COMPOUNDS AS PLATELET ADENOSINE DIPHOSPHATE RECEPTOR ANTAGONISTS
  申请人：Schering Aktiengesellschaft

  公开号：EP1578423A1

  公开（公告）日：2005-09-28