benzyl 1-benzyl-2-oxo-1,2-dihydronicotinate | 918803-88-0

• 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: benzyl 1-benzyl-2-oxo-1,2-dihydronicotinate
• 英文别名: Benzyl 1-benzyl-2-oxopyridine-3-carboxylate
• CAS: 918803-88-0
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: AWFFRHJYHMLQHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 1-benzyl-2-oxo-1,2-dihydronicotinate 在 manganese(IV) oxide 、 copper(l) iodide 、 lithium chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 benzyl 1-benzyl-2-oxo-4-phenyl-1,2-dihydronicotinate
  参考文献：
  名称：

  Discovery of pyridine-2-ones as novel class of multidrug resistance (MDR) modulators: First structure–activity relationships

  摘要：

  A novel facile synthesis led to pyridine-2-one target structures of which first series with varying substituents have been yielded and biologically characterized as novel multidrug resistance (MDR) modulators inhibiting P-glycoprotein (P-gp). Structure-activity relationships prove a dependency of the MDR-modulating properties from the kind and positioning of hydrogen bond acceptor functions within the molecular skeleton. Cyano functions turned out as biologically effective substituents for a potential hydrogen bonding to the protein target structure. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.005
• 作为产物：
  描述：

  benzyl 2-methoxypyridine-3-carboxylate 、 溴甲苯 反应 20.0h， 以8%的产率得到benzyl 1-benzyl-2-oxo-1,2-dihydronicotinate
  参考文献：
  名称：

  Discovery of pyridine-2-ones as novel class of multidrug resistance (MDR) modulators: First structure–activity relationships

  摘要：

  A novel facile synthesis led to pyridine-2-one target structures of which first series with varying substituents have been yielded and biologically characterized as novel multidrug resistance (MDR) modulators inhibiting P-glycoprotein (P-gp). Structure-activity relationships prove a dependency of the MDR-modulating properties from the kind and positioning of hydrogen bond acceptor functions within the molecular skeleton. Cyano functions turned out as biologically effective substituents for a potential hydrogen bonding to the protein target structure. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.005

文献信息

• Introduction of the Acetate Unit to the 2-Pyridinone Ring System and Its Application to the Synthesis of (20<i>S</i>)-Camptothecin DE Ring System
  作者：Kou Hiroya、Kei Kawamoto、Takao Sakamoto

  DOI：10.1055/s-2006-950433

  日期：2006.9

  The DE ring system of (20S)-camptothecin had been ­prepared from commercially available nicotinic acid in six steps ­utilizing the nucleophilic addition reaction of the silyl ketene acetal to the pyridinone ring as a key step.

  (20S)-喜树碱的 DE 环系统是利用硅酮缩醛与吡啶酮环的亲核加成反应作为关键步骤，通过六个步骤从市售烟酸中制备出来的。
• Discovery of pyridine-2-ones as novel class of multidrug resistance (MDR) modulators: First structure–activity relationships
  作者：Sören Krawczyk、Monika Otto、Alexander Otto、Claudius Coburger、Martin Krug、Marianne Seifert、Volkmar Tell、Joséf Molnár、Andreas Hilgeroth

  DOI：10.1016/j.bmc.2011.09.005

  日期：2011.11

  A novel facile synthesis led to pyridine-2-one target structures of which first series with varying substituents have been yielded and biologically characterized as novel multidrug resistance (MDR) modulators inhibiting P-glycoprotein (P-gp). Structure-activity relationships prove a dependency of the MDR-modulating properties from the kind and positioning of hydrogen bond acceptor functions within the molecular skeleton. Cyano functions turned out as biologically effective substituents for a potential hydrogen bonding to the protein target structure. (C) 2011 Elsevier Ltd. All rights reserved.