N-(phenazin-2-yl)acetamide | 28124-26-7

• 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)acetamide
• 英文别名: N-phenazin-2-yl-acetamide；N-Phenazin-2-yl-acetamid；2-Acetamino-phenazin；N-(2-Phenazinyl)acetamide；N-phenazin-2-ylacetamide
• CAS: 28124-26-7
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: WWKXQHLLOBUTGE-UHFFFAOYSA-N

物化性质

• 沸点：
  532.6±15.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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)acetamide
  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

• Phenazines—I
  作者：A. Gray、F.G. Holliman

  DOI：10.1016/s0040-4020(01)99275-0

  日期：1962.1

  The nitration of 1-methoxy- and 1-aminophenazine gives the 4-nitro derivatives from which various 1,4-disubstituted phenazines have been obtained. Data on the absorption spectra of these compounds are recorded.

  1-甲氧基-和1-氨基吩嗪的硝化产生了4-硝基衍生物，从中已经获得了各种1,4-二取代的吩嗪。记录这些化合物的吸收光谱数据。
• Kehrmann; Hoehn, Helvetica Chimica Acta, 1925, vol. 8, p. 222
  作者：Kehrmann、Hoehn

  DOI：——

  日期：——
• Kehrmann; Mermod, Helvetica Chimica Acta, 1927, vol. 10, p. 64
  作者：Kehrmann、Mermod

  DOI：——

  日期：——
• [EN] METHODS FOR REDUCING SUPEROXIDE ANIONS IN EUKARYOTIC ORGANISMS<br/>[FR] PROCÉDÉS DE RÉDUCTION DES ANIONS SUPEROXYDE DANS DES ORGANISMES EUCARYOTES
  申请人：HEALTH RESEARCH INC

  公开号：WO2011119798A1

  公开（公告）日：2011-09-29

  Provided are methods and compositions for reducing superoxide anions such that a prophylactic or therapeutic effect against conditions associated with excess oxidative stress achieved. The compositions and methods provide for reducing inflammation and for enhancing lifespan of eukaryotic organisms. A screen for identifying compounds that can be used in these methods is also provided.
• 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.

表征谱图