methyl 4-(benzyloxy)quinoline-2-carboxylate | 102028-50-2

• 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: methyl 4-(benzyloxy)quinoline-2-carboxylate
• 英文别名: 4-benzyloxy-quinoline-2-carboxylic acid methyl ester；4-Benzyloxy-chinolin-2-carbonsaeure-methylester；methyl 4-phenylmethoxyquinoline-2-carboxylate
• CAS: 102028-50-2
• 化学式: C₁₈H₁₅NO₃
• mdl: MFCD27455533
• 分子量: 293.322
• InChiKey: XDAYBHABPFHCBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(benzyloxy)quinoline-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 4-benzyloxyquinoline-2-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis and Activity of Ascorbic Acid Prodrugs of Nipecotic, Kynurenic and Diclophenamic Acids, Liable to Increase Neurotropic Activity

  摘要：

  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.

  DOI：

  10.1021/jm015556r
• 作为产物：
  描述：

  犬尿喹酸 在 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 4-(benzyloxy)quinoline-2-carboxylate
  参考文献：
  名称：

  Design, Synthesis and Activity of Ascorbic Acid Prodrugs of Nipecotic, Kynurenic and Diclophenamic Acids, Liable to Increase Neurotropic Activity

  摘要：

  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.

  DOI：

  10.1021/jm015556r

文献信息

• Photoreductive Removal of <i>O</i>-Benzyl Groups from Oxyarene <i>N</i>-Heterocycles Assisted by <i>O</i>-Pyridine–pyridone Tautomerism
  作者：Aleksandar R. Todorov、Tom Wirtanen、Juho Helaja

  DOI：10.1021/acs.joc.7b02775

  日期：2017.12.15

  groups from oxyarene N-heterocycles at positions capable for 2-/4-O-pyridine–2-/4-pyridone tautomerism. Blue light irradiation, a [Ru] or [Ir] photocatalyst, and ascorbic acid in a water–acetonitrile solution debenzylates a variety of aryl N-heterocycles cleanly and selectively. Ascorbic acid has two functions in the reaction. On the one hand, it protonates the N-heterocycles that reduces their reduction

  已经开发出了简便的光还原方案，可以从氧化芳烃N-杂环上的苄基O-保护基团去除能够使2- / 4- O-吡啶-2- / 4-吡啶酮互变异构的位置。蓝光照射，[Ru]或[Ir]光催化剂和水-乙腈溶液中的抗坏血酸可选择性地使各种芳基N-杂环脱苄基。抗坏血酸在反应中具有两个功能。一方面，它使N-杂环质子化，从而显着降低其还原电位，另一方面，它作为牺牲性还原剂。以CPCM-B3LYP / 6-31 + G **水平计算的还原势和自由能垒可以预测所研究底物的反应性。
• Design, synthesis and in vitro evaluation on HRPE cells of ascorbic and 6-bromoascorbic acid conjugates with neuroactive molecules
  作者：Stefano Manfredini、Silvia Vertuani、Barbara Pavan、Federica Vitali、Martina Scaglianti、Fabrizio Bortolotti、Carla Biondi、Angelo Scatturin、Puttur Prasad、Alessandro Dalpiaz

  DOI：10.1016/j.bmc.2004.07.043

  日期：2004.10

  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.
• 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.