Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 11, pp 2085–2092 | Cite as

Synthesis, docking, and cytotoxic activities of novel 2-aryl-4-(arylamino)quinazolines

  • Nasrin Rahmannejadi
  • Soghra Khabnadideh
  • Issa Yavari
Original Paper


A synthesis of functionalized 2-aryl-4-(arylamino)quinazolines from 4-chloro-2-arylquinazolines (derived from 2-arylquinazolin-4(3H)-one) and 5-chloroaniline derivatives in DMF is described. The interaction of 2-aryl-4-(arylamino)quinazolines with their biological target, human epithelial growth factor receptor (EGFR), was investigated by molecular docking. Docking results indicated lower binding energy for all compounds towards EGFR active sites. The cytotoxic activities of fifteen 2-aryl-4-(arylamino)quinazolines are evaluated against lung adenocarcinoma (A549) and ovarian cancer (SKOV3) cell lines using MTT method. Our results demonstrated that among the tested compounds 2-(4-bromophenyl)-N-(5-chloro-2-methylphenyl)quinazolin-4-amine and N-(2,5-dichlorophenyl)-2-(4-chlorophenyl)quinazolin-4-amine showed desirable cytotoxic activities on both cell lines. Compounds 2-(3-bromophenyl)-N-(5-chloro-2-methylphenyl)quinazolin-4-amine and 2-(4-bromophenyl)-N-(2,5-dichlorophenyl)quinazolin-4-amine displayed appropriate cytotoxic activities on A549 and SKOV3 cell lines, respectively.

Graphical abstract


Heterocyclic synthesis 4-(Arylamino)quinazolines Docking Cytotoxic assay 4-Chloro-2-arylquinazoline 

Supplementary material

706_2018_2270_MOESM1_ESM.docx (1008 kb)
Supplementary material 1 (DOCX 1007 kb)


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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  • Nasrin Rahmannejadi
    • 1
  • Soghra Khabnadideh
    • 2
  • Issa Yavari
    • 3
  1. 1.Department of Chemistry, Science and Research BranchIslamic Azad UniversityTehranIran
  2. 2.Pharmaceutical Science Research CenterShiraz University of Medical SciencesShirazIran
  3. 3.Department of ChemistryTarbiat Modares UniversityTehranIran

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