1-pentyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid ethyl ester | 148237-79-0

• 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: 1-pentyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 4-hydroxy-1-pentyl-2-oxo-1,2-dihydroquinoline-3-carboxylate；ethyl 1-pentyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxylate；Ethyl 4-hydroxy-2-oxo-1-pentyl-1,2-dihydroquinoline-3-carboxylate；ethyl 4-hydroxy-2-oxo-1-pentylquinoline-3-carboxylate
• CAS: 148237-79-0
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: QSJZIXCXEQQEME-UHFFFAOYSA-N

物化性质

• 沸点：
  426.4±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  1-pentyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid ethyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 以92%的产率得到4-hydroxy-2-oxo-1-pentyl-1,2-dihydroquinoline-3-carboxylic acid hydrazide
  参考文献：
  名称：

  4-Hydroxyquinolones-2

  摘要：

  DOI：

  10.1007/bf00531325
• 作为产物：
  描述：

  2-Pentylamino-benzoic acid ethyl ester 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 1-pentyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid ethyl ester
  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

• Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 7. Synthesis and Pharmacological Evaluation of 4-Quinolone-3-carboxamides and 4-Hydroxy-2-quinolone-3-carboxamides as High Affinity Cannabinoid Receptor 2 (CB2R) Ligands with Improved Aqueous Solubility
  作者：Claudia Mugnaini、Antonella Brizzi、Alessia Ligresti、Marco Allarà、Stefania Lamponi、Federica Vacondio、Claudia Silva、Marco Mor、Vincenzo Di Marzo、Federico Corelli

  DOI：10.1021/acs.jmedchem.5b01559

  日期：2016.2.11

  type-2 receptor (CB2R) ligands. With the aim to improve their physicochemical properties, basically aqueous solubility, two different approaches were followed, entailing the substitution of the alkyl chain with a basic replacement or scaffold modification to 4-hydroxy-2-quinolone structure. According to the first approach, compound 6d was obtained, showing slightly reduced receptor affinity (Ki = 60

  长期以来，人们公认4-喹诺酮-3-羧酰胺衍生物是有效的选择性大麻素2型受体（CB2R）配体。为了改善其理化性质，基本上是水溶性，采用了两种不同的方法，即用对4-羟基-2-喹诺酮结构的碱性取代或支架修饰来取代烷基链。根据第一种方法，获得化合物6d，与先导化合物4相比，其受体亲和力略有降低（K i = 60 nM）（0.8 nM），但溶解度大大提高（取决于培养基的pH值，为400-3400倍）。另一方面，从4-喹诺酮结构转变为4-羟基-2-喹诺酮结构使得能够发现一类新型的CB2R配体，例如7b和7c，其特征在于K i <1 nM和选择性指数[SI = K i（CB1R）/ K i（CB2R）]>1300。在pH 7.4下，化合物7c的溶解度比4高100倍。
• 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。
• 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.
• 4-hydroxy-2-quinolones 165*. 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carbaldehydes and their thiosemicarbazones. Synthesis, structure, and biological properties
  作者：I. V. Ukrainets、Liu Yangyang、A. A. Tkach、O. V. Gorokhova、A. V. Turov

  DOI：10.1007/s10593-009-0327-2

  日期：2009.6

  Two variants are discussed of the synthesis of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid beta-N-tosylhydrazides which undergo a McFayden-Stevens reaction to give 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbaldehydes in high yields. It was shown that the thiosemicarbazones prepared from them exist in the solid state exclusively in the syn-form while in solution a hydrazone. <-> enhydrazine tautomerism is observed. The results of a study of the antitubercular activity of the synthesized compounds are reported.
• 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.