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

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Abstract

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.

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Authors and Affiliations

  1. Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran

    Nasrin Rahmannejadi

  2. Pharmaceutical Science Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

    Soghra Khabnadideh

  3. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

    Issa Yavari

Authors
  1. Nasrin Rahmannejadi
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  2. Soghra Khabnadideh
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  3. Issa Yavari
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Correspondence to Issa Yavari.

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Rahmannejadi, N., Khabnadideh, S. & Yavari, I. Synthesis, docking, and cytotoxic activities of novel 2-aryl-4-(arylamino)quinazolines. Monatsh Chem 149, 2085–2092 (2018). https://doi.org/10.1007/s00706-018-2270-3

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  • DOI: https://doi.org/10.1007/s00706-018-2270-3

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