2-amino-7-dimethylamino-4-(4-dimethylaminonaphthalen-1-yl)-4H-chromene-3-carbonitrile | 1384170-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-7-dimethylamino-4-(4-dimethylaminonaphthalen-1-yl)-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-7-(dimethylamino)-4-[4-(dimethylamino)naphthalen-1-yl]-4H-chromene-3-carbonitrile
• CAS: 1384170-58-4
• 化学式: C₂₄H₂₄N₄O
• 分子量: 384.481
• InChiKey: XWCSZMDVKNZVMD-UHFFFAOYSA-N

物化性质

• 沸点：
  610.3±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-二甲氨基-1-萘醛 、 丙二腈 、 3-羟基-N,N-二甲基苯胺 在 三乙胺 作用下， 150.0 ℃ 、2.07 MPa 条件下， 反应 0.08h， 以7%的产率得到2-amino-7-dimethylamino-4-(4-dimethylaminonaphthalen-1-yl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  New substituted 4H-chromenes as anticancer agents

  摘要：

  As a continuation of our efforts to discover and develop small molecules as anticancer agents, we identified GRI-394837 as an initial hit from similarity search on RGD and its analogs. Based on GRI-394837, we designed and synthesized a focused set of novel chromenes (4a-e) in a single step using microwave method. All five compounds showed activity in the nanomolar range (IC50: 7.4-640 nM) in two melanoma, three prostate and four glioma cancer cell lines. The chromene 4e is active against all the cell lines and particularly against the A172 human glioma cell line (IC50: 7.4 nM). Interestingly, in vitro tubulin polymerization assay shows 4e to be a weak tubulin polymerization inhibitor but it shows very strong cytotoxicity in cellular assays, therefore there must be additional unknown mechanism(s) for the anticancer activity. Additionally, the strong antiproliferative activity was verified by one of the selected chromene (4a) by the NCI 60 cell line screen. These results strongly suggest that the novel chromenes could be further developed as a potential therapeutic agent for a variety of aggressive cancers. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.04.074

文献信息

• New substituted 4H-chromenes as anticancer agents
  作者：Shivaputra A. Patil、Jin Wang、Xiaochen S. Li、Jianjun Chen、Terreia S. Jones、Amira Hosni-Ahmed、Renukadevi Patil、William L. Seibel、Wei Li、Duane D. Miller

  DOI：10.1016/j.bmcl.2012.04.074

  日期：2012.7

  As a continuation of our efforts to discover and develop small molecules as anticancer agents, we identified GRI-394837 as an initial hit from similarity search on RGD and its analogs. Based on GRI-394837, we designed and synthesized a focused set of novel chromenes (4a-e) in a single step using microwave method. All five compounds showed activity in the nanomolar range (IC50: 7.4-640 nM) in two melanoma, three prostate and four glioma cancer cell lines. The chromene 4e is active against all the cell lines and particularly against the A172 human glioma cell line (IC50: 7.4 nM). Interestingly, in vitro tubulin polymerization assay shows 4e to be a weak tubulin polymerization inhibitor but it shows very strong cytotoxicity in cellular assays, therefore there must be additional unknown mechanism(s) for the anticancer activity. Additionally, the strong antiproliferative activity was verified by one of the selected chromene (4a) by the NCI 60 cell line screen. These results strongly suggest that the novel chromenes could be further developed as a potential therapeutic agent for a variety of aggressive cancers. (C) 2012 Published by Elsevier Ltd.