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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
  • 34 Downloads

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.

Graphical abstract

Keywords

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)

References

  1. 1.
    Chandrika PM, Yakaiah T, Rao ARR, Narsaiah B, Reddy NC, Sridhar V, Rao JV (2008) Eur J Med Chem 43:846CrossRefGoogle Scholar
  2. 2.
    Abdel-Gawad NM, Georgey HH, Youssef RM, El-Sayed NA (2010) Eur J Med Chem 45:6058CrossRefGoogle Scholar
  3. 3.
    Lu L, Zhang M-M, Jiang H, Wang XS (2013) Tetrahedron Lett 54:757CrossRefGoogle Scholar
  4. 4.
    El-Azab AS, Al-Omar MA, Alaa AM, Abdel-Aziz AA, Abdel-Aziz NI, El-Sayed MA, Aleisa AM, Sayed-Ahmed MM, Abdel-Hamide SG (2010) Eur J Med Chem 45:4188CrossRefGoogle Scholar
  5. 5.
    Alagarsamy V, Raja Solomon V, Sheorey RV, Jayakumar R (2009) Chem Biol Drug Des 73:471CrossRefGoogle Scholar
  6. 6.
    Huang C, Fu Y, Fu H, Jiang Y, Zhao Y (2008) Chem Commun 47:6333CrossRefGoogle Scholar
  7. 7.
    Rajput R, Mishra AP (2012) Int J Pharm Pharm Sci 4:66Google Scholar
  8. 8.
    Wright SW, Carlo AA, Carty MD, Danley DE, Hageman DL, Karam GA, Levy CB, Mansour MN, Mathiowetz AM, McClure LD, McPherson RK, Pandit J, Pustilnik LR, Schulte GK, Soeller WC, Treadway JL, Wang IK, Bauer PH (2002) J Med Chem 45:3865CrossRefGoogle Scholar
  9. 9.
    Chandregowda V, Kush AK, Reddy GC (2009) Eur J Med Chem 44:3046CrossRefGoogle Scholar
  10. 10.
    Alagarsamy V, Pathak US (2007) Bioorg Med Chem 15:3457CrossRefGoogle Scholar
  11. 11.
    Maruthamuthu M, Rajam S, Stella CR, Bharathi Dileepan AG, Ranjith R (2016) J Chem Pharm Res 8:505Google Scholar
  12. 12.
    Zein MA (2012) J Am Sci 8Google Scholar
  13. 13.
    Bedi PMS, Kumar V, Mahajan MP (2004) Bioorg Med Chem Lett 14:5211CrossRefGoogle Scholar
  14. 14.
    Mishra AD (2012) Nepal J Sci Tech 12:133CrossRefGoogle Scholar
  15. 15.
    Shewchuk L, Hassell A, Wisely B, Rocque W, Holmes W, Veal J, Kuyper LF (2000) J Med Chem 43:133CrossRefGoogle Scholar
  16. 16.
    Marzaro G, Guiotto A, Chilin A (2012) Expert Opin Ther Pat 22:223CrossRefGoogle Scholar
  17. 17.
    Sriram KB, Savarimuthu Francis SM, Tan ME, Bowman RV, Yang IA, Fong KM (2010) Curr Respir Med Rev 6:310CrossRefGoogle Scholar
  18. 18.
    Rajasekaran A, Rajamanickam V, Darlinquine S (2013) Eur Rev Med Pharmacol Sci 17:95PubMedGoogle Scholar
  19. 19.
    Jiang JB, Hesson DP, Dusak BA, Dexter DL, Kang GJ, Hamel E (1990) J Med Chem 33:1721CrossRefGoogle Scholar
  20. 20.
    Larksarp C, Alper H (2000) J Org Chem 65:2773CrossRefGoogle Scholar
  21. 21.
    Akazome M, Yamamoto J, Kondo T, Watanabe Y (1995) J Organomet Chem 494:229CrossRefGoogle Scholar
  22. 22.
    Abdel-Jalil RJ, Voelter W, Saeed M (2004) Tetrahedron Lett 45:3475CrossRefGoogle Scholar
  23. 23.
    Jing XB, Li Z, Pan X, Shi YC (2008) J Chin Chem Soc 55:1145CrossRefGoogle Scholar
  24. 24.
    Haghighijoo Z, Eskandari M, Khabnadideh S (2017) Med Res Arch 5:5CrossRefGoogle Scholar
  25. 25.
    Haghighijoo Z, Rezaei Z, Taheri S, Jani M, Khabnadideh S (2015) Trends Pharm Sci 1:173Google Scholar
  26. 26.
    Khabnadideh S, Pez D, Musso A, Brun R, Pérez LMR, González-Pacanowska D, Gilbert IH (2005) Bioorg Med Chem 13:2637CrossRefGoogle Scholar
  27. 27.
    Humphrey W, Dalke A, Schulten K (1996) J Mol Graph 14:33CrossRefGoogle Scholar
  28. 28.
    Fereidoonnezhad M, Faghih Z, Mojaddami A, Sakhteman A, Rezaei Z (2016) Dent J 1:5Google Scholar
  29. 29.
    Fereidoonnezhad M, Faghih Z, Mojaddami A, Tabaei SMH, Rezaei Z (2016) J Sci Islam Repub Iran 27:39Google Scholar
  30. 30.
    Sun J, Wang XY, Lv PC, Zhu HL (2015) Sci Rep 5:13934CrossRefGoogle Scholar
  31. 31.
    Li Z, Gu J, Zhuang H, Kang L, Zhao X, Guo Q (2015) Appl Soft Comput 26:299CrossRefGoogle Scholar
  32. 32.
    Faghih Z, Neshat A, Wojtczak A, Faghih Z, Mohammadi Z, Varestan S (2017) Inorg Chim Acta 471:404CrossRefGoogle Scholar
  33. 33.
    Fereidoonnezhad M, Niazi Ahmadipour T, Mirzaee Z, Faghih Z, Faghih Z, Shahsavari HR (2017) Eur J Inorg Chem 2017:2247CrossRefGoogle Scholar

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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