Methyl 3-(benzyloxy)-6-methoxyquinoline-2-carboxylate | 171917-55-8

• 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 3-(benzyloxy)-6-methoxyquinoline-2-carboxylate
• 英文别名: Methyl 6-methoxy-3-phenylmethoxyquinoline-2-carboxylate
• CAS: 171917-55-8
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: UNLOZHSFUJLKPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-(benzyloxy)-6-methoxyquinoline-2-carboxylate 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 luzopeptin C
  参考文献：
  名称：

  Luzopeptin A-C 和 Quinoxapeptin A-C 的全合成和比较评价

  摘要：

  公开了 luzopeptin A-C 和 quinoxapeptin A-C（带有两个侧链杂环生色团的 C2 对称环状缩肽头肽）全合成的全部细节，并用于建立 quinoxapeptin 的相对和绝对构型。该方法的关键要素包括后期引入发色团和倒数第二个 l-Htp 酰化，从而允许从常见的高级中间体合成 luzopeptins、quinoxapeptins 和结构类似物。在单个二级酰胺位点进行的 32 元环的对称五肽偶联和大环化提供了常见的环状十肽。在令人惊讶的有效无外消旋化条件下，通过在最终偶联中安装不稳定酯实现了所需五肽的会聚制备。quinoxapeptins 被证明通过高亲和力的双嵌入与 DNA 结合，类似于 Sandramycin 和 luzopeptins。显着的相似之处...

  DOI：

  10.1021/ja993019e
• 作为产物：
  描述：

  2-氨基-5-甲氧基苯甲醛 在 四丁基碘化铵 氢氧化钾 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 Methyl 3-(benzyloxy)-6-methoxyquinoline-2-carboxylate
  参考文献：
  名称：

  A Modified Friedlander Condensation for the Synthesis of 3-Hydroxyquinoline-2-carboxylates

  摘要：

  DOI：

  10.1021/jo00127a055

文献信息

• Total Synthesis of Luzopeptins A−C
  作者：Dale L. Boger、Mark W. Ledeboer、Masaharu Kume

  DOI：10.1021/ja983925b

  日期：1999.2.1
• Synthesis of key sandramycin analogs: systematic examination of the intercalation chromophore
  作者：Dale L. Boger、Jyun-Hung Chen、Kurt W. Saionz、Qing Jin

  DOI：10.1016/s0968-0896(97)10014-1

  日期：1998.1

  The preparation and examination of 2-22 constituting a systematic study of the chromophore of sandramycin (1) are detailed. Fluorescence quenching studies were used to establish binding constants for 1-24 within calf thymus DNA, within a single high affinity bis-intercalation binding site 5'-d(GCATGC)(2), and to establish the preference for sandramycin binding to 5'-d(GCXXGC)(2) where XX = AT, TA, GC, and CG. From the latter studies, sandramycin was found to exhibit a preference that follows the order: 5'-d(GCATGC)(2) > 5'-d(GCGCGC)(2), Delta Delta G degrees = 0.3 kcal/mol > 5'-d(GCTAGC)(2), 5'-d(GCCGGC)(2), Delta Delta G degrees = 0.6 kcal/mol although it binds with high affinity to all four deoxyoligonucleotides. The two highest affinity sequences constitute repeating 5'-PuPy motifs with each intercalation event occurring at a 5'-PyPu step. The most effective sequence constitutes the less stable duplex, contains the sterically most accessible minor groove central to the bis-intercalation site, and the ability to accept two gly-NH/T C2 carbonyl H-bonds identified in prior NMR studies. Similarly, the contribution of the individual structural features of the chromophore were assessed with the high affinity duplex sequence 5'-d(GCATGC)(2). To a first approximation, the cytotoxic properties were found to parallel trends established in the DNA binding affinities. The exception to this generalization was 4 which lacks the sandramycin chromophore phenol. Although typically 4-10x less potent than sandramycin against leukemia cell lines, it proved to be 1-10,000x more potent against melanomas, carcinomas, and adenocarcinomas exhibiting IC50 values of IpM-10 nM placing it among the most potent agents identified to date. Additionally, the first disclosure of the HIV-1 reverse transcriptase inhibitory activity of sandramycin (1) as well as that of its key analogs are described and define the chromophore structural features required for their exceptional potency. Two analogs, 18 and 3, roughly maintain the HIV-I reverse transcriptase inhibitory potency of 1 but exhibit substantially diminished cytotoxic activity (10(2) - 10(3)x). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Total Synthesis and Comparative Evaluation of Luzopeptin A−C and Quinoxapeptin A−C
  作者：Dale L. Boger、Mark W. Ledeboer、Masaharu Kume、Mark Searcey、Qing Jin

  DOI：10.1021/ja993019e

  日期：1999.12.1

  Full details of the total syntheses of luzopeptin A−C and quinoxapeptin A−C, C2-symmetric cyclic depsidecapeptides bearing two pendant heterocyclic chromophores, are disclosed and serve to establish the quinoxapeptin relative and absolute configuration. Key elements of the approach include the late-stage introduction of the chromophore and penultimate l-Htp acylation permitting the divergent synthesis

  公开了 luzopeptin A-C 和 quinoxapeptin A-C（带有两个侧链杂环生色团的 C2 对称环状缩肽头肽）全合成的全部细节，并用于建立 quinoxapeptin 的相对和绝对构型。该方法的关键要素包括后期引入发色团和倒数第二个 l-Htp 酰化，从而允许从常见的高级中间体合成 luzopeptins、quinoxapeptins 和结构类似物。在单个二级酰胺位点进行的 32 元环的对称五肽偶联和大环化提供了常见的环状十肽。在令人惊讶的有效无外消旋化条件下，通过在最终偶联中安装不稳定酯实现了所需五肽的会聚制备。quinoxapeptins 被证明通过高亲和力的双嵌入与 DNA 结合，类似于 Sandramycin 和 luzopeptins。显着的相似之处...
• A Modified Friedlander Condensation for the Synthesis of 3-Hydroxyquinoline-2-carboxylates
  作者：Dale L. Boger、J.-H. Chen

  DOI：10.1021/jo00127a055

  日期：1995.11