ethyl 1-propyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxylate | 148237-78-9

• 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-propyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxylate
• 英文别名: ethyl ester of 1-propyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid；ethyl 4-hydroxy-1-propyl-2-oxo-1,2-dihydroquinoline-3-carboxylate；ethyl 4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylate；1-propyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid ethyl ester；3-ethoxycarbonyl-4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline；ethyl 4-hydroxy-2-oxo-1-propylquinoline-3-carboxylate
• CAS: 148237-78-9
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: RNDGIBAFDFSHNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  401.2±45.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-propyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxylate 在 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以84%的产率得到4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  4-羟基-2-喹诺酮类化合物132. 1-R-4-羟基-2-氧-2-氧-1,2-二氢喹啉-3-羧酸2-硝基苄基肼的合成，化学和生物学性质

  摘要：

  DOI：

  10.1007/s10593-007-0221-8
• 作为产物：
  描述：

  ethyl 2-(propylamino)benzoate 在 盐酸 、 氢氧化钾 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 ethyl 1-propyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-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

• N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: Design, synthesis, biological evaluation and target identification
  作者：Wenjie Xue、Xueyao Li、Guixing Ma、Hongmin Zhang、Ya Chen、Johannes Kirchmair、Jie Xia、Song Wu

  DOI：10.1016/j.ejmech.2019.112022

  日期：2020.2

  new class of antibacterial agents, as one of its derivatives was identified as an antibacterial agent against S. aureus. However, no potency-directed structural optimization has been performed. In this study, we designed and synthesized 37 derivatives, and evaluated their antibacterial activity against S. aureus ATCC29213, which led to the identification of ten potent antibacterial agents with minimum

  由于发生抗生素抗性，细菌感染性疾病已成为对公共健康的严重威胁。为了克服抗生素抗性，迫切需要新型抗生素。N-噻二唑-4-羟基-2-喹诺酮-3-羧酰胺是一类潜在的新型抗菌剂，因为其衍生物之一被确定为针对金黄色葡萄球菌的抗菌剂。但是，尚未执行效能导向的结构优化。在这项研究中，我们设计和合成了37种衍生物，并评估了它们对金黄色葡萄球菌ATCC29213的抗菌活性，从而鉴定出十种有效抑菌剂，其最低抑菌浓度（MIC）值均低于1μg/ mL。接下来，我们针对一组抗药性临床分离株进行了细菌生长抑制测定，包括耐甲氧西林的金黄色葡萄球菌，以及对HepG2和HUVEC细胞的细胞毒性测定。一种被测试的化合物，称为1-乙基-4-羟基-2-氧代-N-（5-（噻唑-2-基）-1,3,4-噻二唑-2-基）-1,2-二氢喹啉-与万古霉素相比，3-羧酰胺（g37）对被测菌株的抗菌力（MIC：0.25-1μg/ mL对1-64μg/
• 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.
• 4-hydroxy-2-quinolones. 149*. Synthesis, chemical transformations, and biological properties of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-4-carboxylic acids
  作者：I. V. Ukrainets、A. A. Tkach、Liu Yang Yang

  DOI：10.1007/s10593-009-0198-6

  日期：2008.11

  Two methods of preparation have been proposed and the synthesis has been effected of a large series of beta-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids. The possibility of using various condensing agents for converting them into the corresponding 1,3,4-oxa-diazoloquinolines has been studied. Results are given of an investigation of the antitubercular activity of the synthesized compounds.
• 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.