ethyl 1-propyl-1,2-dihydro-4-hydroxy-6,7-dimethoxy-2-oxo-quinoline-3-carboxylate | 74500-13-3

• 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-6,7-dimethoxy-2-oxo-quinoline-3-carboxylate
• 英文别名: N-propyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester；Ethyl 4-hydroxy-6,7-dimethoxy-2-oxo-1-propylquinoline-3-carboxylate
• CAS: 74500-13-3
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: RSZMFWDESGBOIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 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：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  对氨基苯甲酸正丙酯 、 ethyl 1-propyl-1,2-dihydro-4-hydroxy-6,7-dimethoxy-2-oxo-quinoline-3-carboxylate 以 甲苯 为溶剂， 以48%的产率得到Propyl 4-[(4-hydroxy-6,7-dimethoxy-2-oxo-1-propylquinoline-3-carbonyl)amino]benzoate
  参考文献：
  名称：

  Design, synthesis and biological characterization of a new class of osteogenic (1H)-quinolone derivatives

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2016.05.062
• 作为产物：
  描述：

  ethyl-2-(3-ethoxy-3-oxo-N-propylpropanamido)-4,5-dimethoxybenzoate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到ethyl 1-propyl-1,2-dihydro-4-hydroxy-6,7-dimethoxy-2-oxo-quinoline-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and biological characterization of a new class of osteogenic (1H)-quinolone derivatives

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2016.05.062

文献信息

• US4190659A
  申请人：——

  公开号：US4190659A

  公开（公告）日：1980-02-26
• US4273930A
  申请人：——

  公开号：US4273930A

  公开（公告）日：1981-06-16