N-(4-methoxyphenethyl)-N-[4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]amine | 1173429-73-6

• 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: N-(4-methoxyphenethyl)-N-[4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]amine
• 英文别名: N-(4-methoxyphenethyl)-4-(methylthio)-3-nitro-4h-chromen-2-amine；N-[2-(4-methoxyphenyl)ethyl]-4-methylsulfanyl-3-nitro-4H-chromen-2-amine
• CAS: 1173429-73-6
• 化学式: C₁₉H₂₀N₂O₄S
• 分子量: 372.445
• InChiKey: ZZHRQGCQFYXUBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-苯基哌啶 、 N-(4-methoxyphenethyl)-N-[4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]amine 以 乙醇 为溶剂， 反应 15.0h， 以86%的产率得到
  参考文献：
  名称：

  Synthesis, in vitro and in silico anti-proliferative activity of 4-aryl-4H-chromene derivatives

  摘要：

  A new series of C4-N,N-dialkylaniline-substituted 4-aryl-4H-chromenes were synthesized, and their anti-proliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549), and cervical cancer (HeLa). The best among them, the 4-aryl-4H-chromene with C4-1-phenylpiperidine substitution was selected for further structure activity relationship (SAR) studies. Among the derivatives, N,6-dimethyl-3-nitro-4-(4-(piperidine-1-yl)phenyl)-4H-chromene-2-amine 3k showed most potent cytotoxic activity against all three cancer cell lines. Toxicity studies revealed that the 4-aryl-4H-chromenes specifically target the cancer cell lines. Molecular docking studies of this compound revealed its efficient interaction with the active site of alpha beta-tubulin protein.

  DOI：

  10.1007/s00044-016-1569-z
• 作为产物：
  描述：

  N-(4-methoxyphenethyl)-N-[(E)-1-(methylsulfanyl)-2-nitro-1-ethenyl]amine 、 水杨醛 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 23.17h， 以73%的产率得到N-(4-methoxyphenethyl)-N-[4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]amine
  参考文献：
  名称：

  Nitroketene acetal chemistry: efficient synthesis of 2-amino-3-nitro-4H-chromenes

  摘要：

  Base-catalyzed reaction of the nitroketene N,S-acetals and the ring substituted 2-hydroxybenzaldehydes afforded a combinatorial library of the 2-alkylamino-3-nitro-4-alkylsulfanyl 4H-chromenes in excellent yields. Nucleophilic displacement of the C4 alkylsulfanyl group with different thiols afforded 4H-chromenes with structural diversity. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.018