propyl 4-(1-methyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-carboxamido)benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: propyl 4-(1-methyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-carboxamido)benzoate
• 英文别名: Propyl 4-{[(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]amino}benzoate；propyl 4-[(4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]benzoate
• 化学式: C₂₁H₂₀N₂O₅
• 分子量: 380.4
• InChiKey: BGWQIYOLWFGCAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基苯胺 以 甲苯 为溶剂， 生成 propyl 4-(1-methyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-carboxamido)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

文献信息

• 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.