N-(phenazin-2-yl)-1-naphthamide | 1491162-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(phenazin-2-yl)-1-naphthamide
• 英文别名: N-phenazin-2-ylnaphthalene-1-carboxamide
• CAS: 1491162-55-0
• 化学式: C₂₃H₁₅N₃O
• 分子量: 349.392
• InChiKey: CARWKMYKTGGDNL-UHFFFAOYSA-N

物化性质

• 沸点：
  531.3±15.0 °C(predicted)
• 密度：
  1.358±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-二硝基二苯胺 在 吡啶 、 5%-palladium/activated carbon 、 氢气 、 magnesium sulfate 作用下， 以 吡啶 、 二氯甲烷 、 乙酸乙酯 、 硝基苯 为溶剂， 反应 48.5h， 生成 N-(phenazin-2-yl)-1-naphthamide
  参考文献：
  名称：

  Synthesis and anticancer activity of some novel 2-phenazinamine derivatives

  摘要：

  In this study, we report the synthesis and spectral characterization of a novel series of 2-phenazinamine derivatives. In vitro evaluation for their anticancer activity toward cultured K562 (human chronic myelogenous leukemia), HepG2 (human hepatocellular carcinoma), MGC803 (human gastric carcinoma), HCT116 (human colorectal carcinoma), MCF7 (human breast adenocarcinoma) cell lines, as well as 293T (epithelial cells from human embryo kidney) non-cancer cell was carried out. The compounds 4, 7,16 and 19 showed good positive anticancer activity in vitro. In particular, compound 4, 2-chloro-N-(phenazin-2-yl)benzamide, possessed a potent anticancer effect comparable to cisplatin against both 1<562 and HepG2 cancer cells but was very low or had no effect against 293T non-cancer cell. Preliminary anticancer mechanism of 4 was investigated by cell apoptosis assays compared with cisplatin using flow cytometry. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.017

文献信息

• Synthesis and anticancer activity of some novel 2-phenazinamine derivatives
  作者：Xiaochun Gao、Yuanyuan Lu、Lei Fang、Xubin Fang、Yingying Xing、Shaohua Gou、Tao Xi

  DOI：10.1016/j.ejmech.2013.07.017

  日期：2013.11

  In this study, we report the synthesis and spectral characterization of a novel series of 2-phenazinamine derivatives. In vitro evaluation for their anticancer activity toward cultured K562 (human chronic myelogenous leukemia), HepG2 (human hepatocellular carcinoma), MGC803 (human gastric carcinoma), HCT116 (human colorectal carcinoma), MCF7 (human breast adenocarcinoma) cell lines, as well as 293T (epithelial cells from human embryo kidney) non-cancer cell was carried out. The compounds 4, 7,16 and 19 showed good positive anticancer activity in vitro. In particular, compound 4, 2-chloro-N-(phenazin-2-yl)benzamide, possessed a potent anticancer effect comparable to cisplatin against both 1<562 and HepG2 cancer cells but was very low or had no effect against 293T non-cancer cell. Preliminary anticancer mechanism of 4 was investigated by cell apoptosis assays compared with cisplatin using flow cytometry. (C) 2013 Elsevier Masson SAS. All rights reserved.