N-[4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-phenylamine | 1173429-67-8

• 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-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-phenylamine
• 英文别名: 4-(methylthio)-3-nitro-N-phenyl-4h-chromen-2-amine；4-methylsulfanyl-3-nitro-N-phenyl-4H-chromen-2-amine
• CAS: 1173429-67-8
• 化学式: C₁₆H₁₄N₂O₃S
• 分子量: 314.365
• InChiKey: BRIZBWAGGQHYTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-phenylamine 、 苯酚 以 乙醇 为溶剂， 反应 14.0h， 以45%的产率得到2-(2-anilino-3-nitro-4H-4-chromenyl)phenol
  参考文献：
  名称：

  Synthesis of 4-(2-hydroxyaryl)-3-nitro-4H-chromenes

  摘要：

  A combinatorial library of 4-(2-hydroxyaryl)-3-nitro-4H-chromenes was synthesized in high yield by C4-SMe substitution in N-alkyl/phenyl 4-(methylthio)-3-nitro-4H-chromen-2-amines with a variety of phenols. The reaction always provided C2 substitution in the phenol ring, dictated by hydrogen bond interactions between the phenolic hydroxyl group and the nitro group in 3-nitro-4H-chromenes. Reduction of the nitro group with concomitant hydrolysis of the enamine in 4-(2-hydroxyaryl)-3-nitro-4H-chromenes with Zn, Ac(2)O in AcOH furnished hybrid amino-acid lactone incorporating ortho-tyrosine and phenyl alanine moieties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.045
• 作为产物：
  描述：

  水杨醛 、 (E)-N-(1-(甲硫基)-2-硝基乙烯基)苯胺 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 31.17h， 以71%的产率得到N-[4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-phenylamine
  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

文献信息

• Synthesis, in vitro and in silico anti-proliferative activity of 4-aryl-4H-chromene derivatives
  作者：A. Parthiban、M. Kumaravel、J. Muthukumaran、R. Rukkumani、R. Krishna、H. Surya Prakash Rao

  DOI：10.1007/s00044-016-1569-z

  日期：2016.7

  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.