ethyl 1-allyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate | 64675-76-9

• 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
• 英文名称: ethyl 1-allyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate
• 英文别名: Ethyl 4-hydroxy-2-oxo-1-(prop-2-en-1-yl)-1,2-dihydroquinoline-3-carboxylate；ethyl 4-hydroxy-2-oxo-1-prop-2-enylquinoline-3-carboxylate
• CAS: 64675-76-9
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: PNHFETLUVCAYSS-UHFFFAOYSA-N

物化性质

• 沸点：
  402.1±45.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-allyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate 在 溴 、 溶剂黄146 作用下， 以92%的产率得到ethyl 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a]quinoline-4-carboxylic acid
  参考文献：
  名称：

  4-羟基-2-喹诺酮类。118. 2-溴甲基-5-氧代-1,2-二氢-5H-恶唑基-[3,2-a]喹啉-4-羧酸及其乙酯的合成，结构和化学性质

  摘要：

  DOI：

  10.1007/s10593-007-0096-8
• 作为产物：
  描述：

  Potassium; 1-allyl-3-ethoxycarbonyl-2-oxo-1,2-dihydro-quinolin-4-olate 在 盐酸 作用下， 反应 1.0h， 以94%的产率得到ethyl 1-allyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  4-羟基-2-喹诺酮类。22. * 1-烷基（芳基）-2-氧代-3-羰乙氧基-4-羟基喹啉及其衍生物的合成及生物学性质

  摘要：

  DOI：

  10.1007/bf01169641

文献信息

• 4-hydroxy-2-quinolones. 191.* synthesis, tautomerism and biological activity of benzimidazol-2-ylamides of 1-r-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids
  作者：I. V. Ukrainets、L. A. Grinevich、A. A. Tkach、O. V. Gorokhova、V. N. Kravchenko、G. Sim

  DOI：10.1007/s10593-011-0673-8

  日期：2011.2

  A series of benzimidazol-2-ylamides of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids was prepared in a search for biologically active compounds. These compounds exist in the crystal exclusively in the amide form, while in solution amide↔imide tautomerism is observed. The results of a study of the antithyroid and antituberculosis activities of these compounds are given.

  为了寻找生物活性化合物，制备了一系列4-羟基-2-氧代-1,2-二氢喹啉-3-羧酸的苯并咪唑-2-基酰胺。这些化合物仅以酰胺形式存在于晶体中，而在溶液中则观察到酰胺↔酰亚胺互变异构现象。给出了这些化合物的抗甲状腺和抗结核活性的研究结果。
• 4-hydroxy-2-quinolones. 169*. synthesis and bromination of 1-allyl-3-(arylamino-methylene)quinoline-2,4-(1h,3h)-diones
  作者：I. V. Ukrainets、Liu Yangyang、N. L. Bereznyakova、A. V. Turov

  DOI：10.1007/s10593-010-0412-6

  日期：2009.10

  Bromination of 1-allyl-substituted 3-(arylaminomethylene)quinoline-2,4-(1H,3H)-diones with one equivalent of molecular bromine in glacial acetic acid and subsequent dilution of the reaction mixture with water is accompanied by halocyclization and hydrolysis to form 2-bromomethyl-5-oxo-1,2 dihydro-5H- oxazolo[3,2-a]quinoline-4-carbaldehyde.
• Design, synthesis and biological characterization of a new class of osteogenic (1H)-quinolone derivatives
  作者：Fabrizio Manetti、Elena Petricci、Annalisa Gabrielli、Andrè Mann、Hélène Faure、Tatiana Gorojankina、Laurent Brasseur、Lucile Hoch、Martial Ruat、Maurizio Taddei

  DOI：10.1016/j.ejmech.2016.05.062

  日期：2016.10

  Smoothened (Smo) is the signal transducer of the Hedgehog (Hh) pathway and its stimulation is considered a potential powerful tool in regenerative medicine to treat severe tissue injuries. Starting from GSA-10, a recently reported Hh activator acting on Smo, we have designed and synthesized a new class of quinolone-based compounds. Modification and decoration of three different portions of the original scaffold led to compounds able to induce differentiation of multipotent mesenchymal cells into osteoblasts. The submicromolar activity of several of these new quinolones (0.4-0.9 mu M) is comparable to or better than that of SAG and purmorphamine, two reference Smo agonists. Structure-activity relationships allow identification of several molecular determinants important for the activity of these compounds. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Discovery of 4-hydroxy-2-oxo-1,2-dihydroquinolines as potential inhibitors of Streptococcus pneumoniae, including drug-resistant strains
  作者：Srigouri Huddar、Chul Min Park、Hyung Jun Kim、Soojin Jang、Sunkyung Lee

  DOI：10.1016/j.bmcl.2020.127071

  日期：2020.5

  New therapies for treating drug-resistant pneumococcal infections are urgently needed. The novel scaffold 6hydroxy-4-oxo-1,2-dihydro-4H-quinoline was shown to have similar efficacies against all three different serotypes of S. pneumoniae, ATCC 49617 (TM) (19F), ATCC BAA-1663 (TM) (15B), and ATCC 700904 (TM) (19A), in a resazurin-based high-throughput screen using the Korea Chemical Bank library. Further studies to identify a new lead with this scaffold, including tricyclic pyrrolo[3,2,1-ij]quinolone and pyrido[3,2,1-ij]quinolone derivatives, led to the identification of 6d, 7d and 12a. Compound 6d (IC50 = 0.92, 0.75, and 0.77 mu M), 7d (IC50 = 0.57, 0.66, and 0.38 mu M) and 12a (IC50, = 0.27, 1.03, and 0.62 mu M) showed submicromolar IC50, values against 19F, 15B, and 19A, respectively, and thus serve as a starting point for further optimization. While some of compounds in this series exhibited acceptable pharmacokinetic profiles in preliminary in vivo rat experiments, the most active compound 12a showed poor solubility and high plasma protein binding. Our current research efforts are focused on optimizing compounds to improve physicochemical properties as well as potency.
• 4-Hydroxy-2-quinolones. 154*. Pyrimidin- 2-ylamides of 1-r-4-hydroxy-2-oxo-1,2-dihydro- quinoline-3-carboxylic acids. synthesis, structure, and properties
  作者：I. V. Ukrainets、A. A. Tkach、L. A. Grinevich、A. V. Turov、O. V. Bevz

  DOI：10.1007/s10593-009-0297-4

  日期：2009.5

  The synthesis of a series of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids pyrimidin-2-ylamides has been carried out with the aim of subsequent microbiological investigation. In acetic acid it was found that these compounds are brominated by 1 equivalent of bromine at position 5 of the pyrimidine ring. The only exception is the 1-allyl derivative which undergoes heterocyclization under these conditions to give 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a]quinoline-4-carboxylic acid pyrimidin-2-ylamide. The results of a study of the antitubercular activity of the synthesized compounds are presented.