6-nitro-N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine | 1444356-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-nitro-N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine
• CAS: 1444356-77-7
• 化学式: C₁₁H₁₀N₄O₇
• 分子量: 310.223
• InChiKey: ZFEHUWNSKIOQRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  150.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (E-)-N-methyl-1-(methylthio)-2-nitroethanamine 、 2-((1E)-2-nitrovinyl)-4-nitrophenol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 反应 15.17h， 以60%的产率得到6-nitro-N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine
  参考文献：
  名称：

  Design, synthesis, molecular docking, and biological evaluation of N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine derivatives as potential anti-cancer agents

  摘要：

  A series of N-methyl-3-nitro-4-(nitromethyl)4H-chromen-2-amine derivatives 8 were synthesized from 2-((E)-2-nitrovinyl)phenol 7 and ((E)-N-methyl)-1-(methylthio)-2-nitroethenamine 5. The cytotoxic activity of these molecules was tested against two cancer cell lines namely HeLa (cervical cancer) and HEp-2 (epidermoid laryngeal carcinoma). Among them, two molecules (4H-chromenes 8h and 8i) displayed potent anti-proliferative activity with IC50 values of 115.04 and 18.96 mu M for HeLa and 86.94 and 25.08 mu M for Hep-2 cell lines, respectively. Morphological evaluation of the cell lines revealed that both 8h and 8i induce the apoptotic process. Molecular docking studies of all the 4H-chromenes 8 with antiapoptotic Bcl-2, Bcl-w, and Bcl-xL proteins revealed that the 4H-chromenes 8h and 8i have good docking score and thus corroborated in vitro studies. Furthermore, evaluation of Lipinski and ADMET properties revealed their drug-like pharmacokinetic profiles. Thus, 4H-chromenes 8h and 8i exhibit promising anti-cancer properties and can be used as lead compounds for further development.

  DOI：

  10.1007/s00044-013-0642-0