4-羟基-2-氧代-1-苯基喹啉-3-羧酸甲酯 | 770711-44-9

• 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: 4-羟基-2-氧代-1-苯基喹啉-3-羧酸甲酯
• 英文名称: methyl 4-hydroxy-2(1H)-oxo-1-phenylquinoline-3-carboxylate
• 英文别名: 4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxylicacid methyl ester；methyl 4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxylate；N-phenyl-3-methoxycarbonyl-4-hydroxy-quinoline-2-one；methyl 4-hydroxy-2-oxo-1-phenylquinoline-3-carboxylate
• CAS: 770711-44-9
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: XWBULOZGQDCZEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  4-羟基-2-氧代-1-苯基喹啉-3-羧酸甲酯 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 N-[2-[5-(dithiolan-3-yl)pentanoylamino]phenyl]-4-hydroxy-2-oxo-1-phenylquinoline-3-carboxamide
  参考文献：
  名称：

  Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents

  摘要：

  A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the alpha-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and for their ability to inhibit in vitro lipoxygenase as well as for their anti-inflammatory activity in vivo. In general, the derivatives were found to be potent antioxidant or anti-inflammatory agents. The results are discussed in terms of structure-activity relationships and an attempt is made to define the structural features required for activity.

  DOI：

  10.1021/jm061173n
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 4-羟基-2-氧代-1-苯基喹啉-3-羧酸甲酯
  参考文献：
  名称：

  A Novel Short-Step Synthesis of Functionalized 4-Hydroxy-2-quinolones Using a 1-Hydroxybenzotriazole Methodology

  摘要：

  提出了一种合成3取代的4-羟基-1-甲基和1-苯基-2-喹啉酮的新方法。该化合物在一步反应中以非常好的产率（51-76%）生产。该方法的主要优点是合成所需时间短，而与先前需要多个步骤和苛刻条件的喹啉衍生物合成方法相比更加高效。

  DOI：

  10.1246/bcsj.77.1505

文献信息

• A Novel Short-Step Synthesis of Functionalized 4-Hydroxy-2-quinolones Using a 1-Hydroxybenzotriazole Methodology
  作者：Lamprini Zikou、Giorgos Athanasellis、Anastasia Detsi、Alexandros Zografos、Christos Mitsos、Olga Igglessi-Markopoulou

  DOI：10.1246/bcsj.77.1505

  日期：2004.8

  A novel method for the synthesis of 3-substituted 4-hydroxy-1-methyl- and 1-phenyl-2-quinolones is presented. The compounds are produced in a one-step reaction in very good yields (51–76%). The major advantage of the methodology is the short time for the synthesis in contrast to previous methodologies requiring several steps and harsh conditions for the synthesis of quinolone derivatives.

  提出了一种合成3取代的4-羟基-1-甲基和1-苯基-2-喹啉酮的新方法。该化合物在一步反应中以非常好的产率（51-76%）生产。该方法的主要优点是合成所需时间短，而与先前需要多个步骤和苛刻条件的喹啉衍生物合成方法相比更加高效。
• Synthesis, X-ray crystallographic study, and biological evaluation of coumarin and quinolinone carboxamides as anticancer agents
  作者：Dimitris Matiadis、Valentina Stefanou、Giorgos Athanasellis、Stylianos Hamilakis、Vickie McKee、Olga Igglessi-Markopoulou、John Markopoulos

  DOI：10.1007/s00706-013-0986-7

  日期：2013.7

  evaluated for its potency in inhibition of cancer cell growth. The structure of N-[2-(dimethylamino) ethyl]-4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxamide was unambiguously confirmed by X-ray diffraction analysis, which revealed the cis conformation of the amide bond resulting from the presence of two intramolecular hydrogen bonds. Graphical Abstract

  摘要合成了一系列香豆素和喹啉酮-3-氨基酰胺衍生物，并评估了其抑制癌细胞生长的潜能。的结构ñ - [2-（二甲基氨基）乙基] -4-羟基-2-氧代-1-苯基-1,2-二氢喹啉-3-甲酰胺是明确地通过X射线衍射分析，其显示所确认的顺式构象由两个分子内氢键的存在而产生的酰胺键 图形概要
• Synthesis and structural studies of quinolone-based Zn(II), Mn(II) and Ca(II) complexes involving supramolecular interactions
  作者：Valentina Stefanou、Dimitris Matiadis、Dimitrios Tsironis、Olga Igglessi-Markopoulou、Vickie Mckee、John Markopoulos

  DOI：10.1080/00958972.2022.2139611

  日期：2022.12.17

  Abstract In the present work, we report a detailed investigation of four supramolecular coordination complexes, Zn(Quino)2(CH3OH)2 2, Zn(Quino)2H2O 3, Mn(Quino)2(CH3OH)2 4 and Ca(Quino)2(CH3OH)2 5, obtained from the self-assembling of Zn(II), Mn(II) and Ca(II) acceptors with the N-phenyl-4-hydroxyquinoline ligand donor QuinoH 1, possessing the β,β′-diketonate moiety. The structure of the supramolecular

  摘要 在目前的工作中，我们报告了对四种超分子配位络合物 Zn(Quino) 2 (CH 3 OH) 2 2、Zn(Quino) 2 H 2 O 3、Mn(Quino) 2 (CH 3 OH) 2的详细研究 4和 Ca(Quino) 2 (CH 3 OH) 2 5，由 Zn(II)、Mn(II) 和 Ca(II) 受体与N -phenyl-4-hydroxyquinoline 配体供体 QuinoH 1自组装获得, 拥有 β,β′ -二酮化部分。已通过单晶 X 射线晶体学研究了分离复合物的超分子排列结构。合成的N-苯基喹诺酮连接体形成具有金属离子配位偏好的 π-π 堆积超分子合成子，已被用于构建配位驱动的自组装“金属超分子”结构。
• Novel Multi-Target Agents Based on the Privileged Structure of 4-Hydroxy-2-quinolinone
  作者：Ioanna Kostopoulou、Andromachi Tzani、Konstantina Chronaki、Kyriakos C. Prousis、Eleni Pontiki、Dimitra Hadjiplavlou-Litina、Anastasia Detsi

  DOI：10.3390/molecules29010190

  日期：——

  4-hydroxy-2quinolinone is investigated through the synthesis of carboxamides and hybrid derivatives, as well as through their bioactivity evaluation, focusing on the ability of the molecules to inhibit the soybean LOX, as an indication of their anti-inflammatory activity. Twenty-one quinolinone carboxamides, seven novel hybrid compounds consisting of the quinolinone moiety and selected cinnamic or benzoic acid

  在这项工作中，通过甲酰胺和杂化衍生物的合成以及它们的生物活性评估，研究了 4-羟基-2喹啉酮的特殊支架，重点关注分子抑制大豆 LOX 的能力，作为其抑制大豆 LOX 的能力的指标。抗炎活性。合成了二十一种喹啉酮甲酰胺、七种由喹啉酮部分和选定的肉桂酸或苯甲酸衍生物组成的新型杂化化合物，以及三种反向酰胺，并根据其 LOX 抑制和抗氧化活性分类为多靶点药物。在所有合成的类似物中，文献中首次引入的喹啉酮-甲酰胺化合物3h和3s表现出最好的LOX抑制活性（IC50 = 10 μM）。此外，羧酰胺 3g 和喹啉酮与乙酰化阿魏酸 11e 的混合物作为多靶点药物出现，揭示了抗氧化和 LOX 抑制活性的结合（3g：LOX 抑制的 IC50 = 27.5 μM，100% 抑制脂质过氧化，67.7% 清除羟基的能力） ABTS 自由基阳离子脱色测定中为 72.4%；11e：LOX 抑制的 IC50 = 52 μM，脂质过氧化的抑制为
• Synthesis and antiproliferative activity of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety
  作者：Qidong Tang、Xin Zhai、Yayi Tu、Ping Wang、Linxiao Wang、Chunjiang Wu、Wenhui Wang、Hongbo Xie、Ping Gong、Pengwu Zheng

  DOI：10.1016/j.bmcl.2016.02.037

  日期：2016.4

  A series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety were synthesized, and evaluated for their antiproliferative activity against 5 cancer cell lines (H460, HT-29, MKN-45, A549, and U87MG). Most compounds showed moderate to excellent potency, and compared to foretinib, the most promising analog 42 (c-Met/Flt-3 IC50 = 1.21/2

  合成了一系列带有2-oxo-4-chloro-1,2，dihydroquinoline-3-carboxamide部分的6,7-di取代-4-phenoxyquinoline衍生物，并评估了它们对5种癌细胞系（H460， HT-29，MKN-45，A549和U87MG）。大多数化合物显示出中等至出色的效力，并且与foretinib相比，最有前途的类似物42（c-Met / Flt-3 IC 50  = 1.21 / 2.15 nM）在体外对H460细胞系的活性提高了6.1倍。在体外评估了化合物42的酶促测定（c-Met，VEGFR-2，Flt-3，PDGFR-β，c-Kit和EGFR）。对接分析表明，化合物42可以与c-Met形成三个氢键 结构与活性之间的关系研究表明，在苯环的4位上，水溶性更强的环状叔胺和吸电子基团有助于抗肿瘤活性。

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