1-(4-chlorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• 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-(4-chlorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-(4-Chlorobenzyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid；1-[(4-chlorophenyl)methyl]-4-oxoquinoline-3-carboxylic acid
• 化学式: C₁₇H₁₂ClNO₃
• mdl: MFCD25952843
• 分子量: 313.74
• InChiKey: RFPVZXXXNLRRHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-chlorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 N,N'-羰基二咪唑 、 羟胺 作用下， 以 乙腈 、 水 为溶剂， 反应 14.5h， 以76.1%的产率得到1-(4-chlorobenzyl)-N-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  作为治疗糖尿病并发症的多功能醛糖还原酶抑制剂的新型喹啉4（1 H）-one衍生物：合成，生物学评估和分子模型研究

  摘要：

  DOI：

  10.1016/j.bmcl.2020.127101
• 作为产物：
  描述：

  4-氧代-1,4-二氢-3-喹啉羧酸甲酯 在 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 1-(4-chlorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  作为治疗糖尿病并发症的多功能醛糖还原酶抑制剂的新型喹啉4（1 H）-one衍生物：合成，生物学评估和分子模型研究

  摘要：

  DOI：

  10.1016/j.bmcl.2020.127101

文献信息

• Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality
  作者：Eric Stern、Giulio G. Muccioli、Barbara Bosier、Laurie Hamtiaux、Régis Millet、Jacques H. Poupaert、Jean-Pierre Hénichart、Patrick Depreux、Jean-François Goossens、Didier M. Lambert

  DOI：10.1021/jm070387h

  日期：2007.11.1

  CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo- 1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure - functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.
• Novel quinolin-4(1H)-one derivatives as multi-effective aldose reductase inhibitors for treatment of diabetic complications: Synthesis, biological evaluation, and molecular modeling studies
  作者：Zhongfei Han、Junkai Zhu、Yunnan Zhang、Ying Zhang、Huiyun Zhang、Gang Qi、Changjin Zhu、Xin Hao

  DOI：10.1016/j.bmcl.2020.127101

  日期：2020.5