N-(3-(4-ethylpiperazin-1-yl)-3-oxopropyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

• 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: N-(3-(4-ethylpiperazin-1-yl)-3-oxopropyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
• 英文别名: N-[3-(4-ethylpiperazin-1-yl)-3-oxopropyl]-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide
• 化学式: C₂₀H₂₆N₄O₄
• 分子量: 386.451
• InChiKey: MGJLLJCPTHVBGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-甲基苯唑 在 盐酸 、 sodium hydride 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 50.16h， 生成 N-(3-(4-ethylpiperazin-1-yl)-3-oxopropyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Design, synthesis and docking studies of novel 1,2-dihydro-4-hydroxy-2-oxoquinoline-3-carboxamide derivatives as a potential anti-proliferative agents

  摘要：

  A new series of 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide hybrids 8a-1 have been designed and synthesized using peptide coupling agents with substituted N-phenyl piperazines and piperidines with good to excellent yields. The synthesized compounds were evaluated for their in vitro anti-proliferative activity against PANC 1, HeLa and MDA-MB-231. The compounds 8d, 8e, 8f, 8g, 8h and 8k exhibited considerable anti-proliferative activity with GI(50) values ranging from 0.15 to 1.4 mu M. The structure and anti-proliferative activity relationship was further supported by in silico molecular docking study of the active compounds against tubulin protein. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.062

文献信息

• Design, synthesis and docking studies of novel 1,2-dihydro-4-hydroxy-2-oxoquinoline-3-carboxamide derivatives as a potential anti-proliferative agents
  作者：Saleha Banu、Rajitha Bollu、Rajashaker Bantu、Lingaiah Nagarapu、Sowjanya Polepalli、Nishant Jain、Radhika Vangala、Vijjulatha Manga

  DOI：10.1016/j.ejmech.2016.09.062

  日期：2017.1

  A new series of 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide hybrids 8a-1 have been designed and synthesized using peptide coupling agents with substituted N-phenyl piperazines and piperidines with good to excellent yields. The synthesized compounds were evaluated for their in vitro anti-proliferative activity against PANC 1, HeLa and MDA-MB-231. The compounds 8d, 8e, 8f, 8g, 8h and 8k exhibited considerable anti-proliferative activity with GI(50) values ranging from 0.15 to 1.4 mu M. The structure and anti-proliferative activity relationship was further supported by in silico molecular docking study of the active compounds against tubulin protein. (C) 2016 Elsevier Masson SAS. All rights reserved.