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Novel 4-aminoquinazoline derivatives as new leads for anticancer drug discovery Cover

Novel 4-aminoquinazoline derivatives as new leads for anticancer drug discovery

Open Access
|Sep 2015

References

  1. 1. S. B. Mhaske and N. P. Argade, The chemistry of recently isolated naturally occurring quinazolinone alkaloids, Tetrahedron62 (2006) 9787–9826; DOI: 10.1016/j.tet.2006.07.098.10.1016/j.tet.2006.07.098
  2. 2. N. J. Liverton, D. J. Armstrong, D. A. Claremon, D. C. Remy, J. J. Baldwin, R. J. Lynch, G. Zhang and R. J. Gould, Nonpeptide glycoprotein IIb/IIIa inhibitors: Substituted quinazolinediones and quinazolinones as potent fibrinogen receptor antagonists, Bioorg. Med. Chem. Lett. 8 (1998) 483–486; DOI: 10.1016/S0960-894X(98)00047-X.10.1016/S0960-894X(98)00047-X
  3. 3. W. Zhang, J. P. Mayer, S. E. Hall and J. A. Weigel, A polymer-bound iminophosphorane approach for the synthesis of quinolones, J. Comb. Chem.3 (2001) 255–256; DOI: 10.1021/cc000113e.10.1021/cc000113e
  4. 4. R. J. Griffin, S. Srinivasan, K. Bowman, A. H. Calvert, N. J. Curtin, D. R. Newell, L. C. Pemberton and B. T. Golding, Resistance-modifying agents. 5. Synthesis and biological properties of quinazolinone inhibitors of the DNA repair enzyme poly (ADP-ribose) polymerase (PARP), J. Med. Chem.41 (1998) 5247–5256; DOI: 10.1021/jm980273t.10.1021/jm980273t
  5. 5. A. N. Hughes, I. Rafi, M. J. Griffin, H. A. Calvert, D. R. Newell, J. A. Calvrte, A. Johnston, N. Clendeninn and A. V. Boddy, Phase I studies with the nonclassical antifolate nolatrexed dihydrochloride (AG337, THYMITAQ) administered orally for 5 days, Clin. Cancer Res.5 (1999) 111–118.
  6. 6. E. Hamel, C. M. Lin, J. Plowman, H. K. Wang, K. H. Lee and K. D. Paull, Antitumor 2,3-dihydro-2-(aryl)-4(1H)-quinazolinone derivatives: Interactions with tubulin, Biochem. Pharmacol. 51 (1996) 53–59; DOI: 10.1016/0006-2952(95)02156-6.10.1016/0006-2952(95)02156-6
  7. 7. S. H. Hwang, A. Rait, K. F. Pirollo, Q. Zhou, V. M. Yenugonda, G. M. Chinigo, M. L. Brown and E. H. Chang, Tumor-targeting nanodelivery enhances the anticancer activity of a novel quinazolinone analogue, Mol. Cancer Ther.7 (2008) 559–568; DOI: 10.1158/1535-7163.MCT-07-0548.10.1158/1535-7163.MCT-07-054818347143
  8. 8. S. K. Kundu, M. P. D. Mahindaratne, M. V. Quintero, A. Bao and G. R. Negrete, One-pot reductive cyclization to antitumor quinazoline precursors, Arkivoc 2008 (2) 33–42.10.3998/ark.5550190.0009.205
  9. 9. M. H. Cohen, J. R. Johnson, Y. F. Chen, R. Sridhara and R. Pazdur, FDA drug approval summary: Erlotinib (Tarceva®) tablets, Oncologist10 (2005) 461–466; DOI: 10.1634/theoncologist.10-7-461.10.1634/theoncologist.10-7-46116079312
  10. 10. K. Abouzid and S. Shouman, Design, synthesis and in vitro antitumor activity of 4-aminoquino-line and 4-aminoquinazoline derivatives targeting EGFR tyrosine kinase, Bioorg. Med. Chem. 16 (2008) 7543–7551; DOI: 10.1016/j.bmc.2008.07.038.10.1016/j.bmc.2008.07.03818678492
  11. 11. A. Witt and J. Bergman, Recent developments in the field of quinazoline chemistry, Curr. Org. Chem. 7 (2003) 659–677; DOI: /10.2174/1385272033486738.10.2174/1385272033486738
  12. 12. H. Wong and A. Gansan, Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies, J. Org. Chem. 65 (2003) 1022–1039; DOI: /10.1021/jo9914364.
  13. 13. J. P. Micheal, Quinoline, quinazoline and acridone alkaloids, Nat. Prod. Rep. 18 (2003) 543–559.10.1039/b005387m11699885
  14. 14. M. M. Ghorab, M. S. Alsaid and R. K. Arafa, Design, synthesis and potential anti-proliferative activity of some novel 4-aminoquinoline derivatives, Acta Pharm.64 (2014) 285–297; DOI: 10.2478/acph-2014-0030.10.2478/acph-2014-003025296675
  15. 15. M. M. Ghorab, F. A. Ragab, S. I. Alqasoumi, A. M. Alafeefy and S. A. Aboulmagd, Synthesis of some new pyrazolo [3, 4-d] pyrimidine derivatives of expected anticancer and radioprotective activity, Eur. J. Med. Chem.45 (2010) 171–178; DOI: 10.1016/j.bmc.–2013.11.042.
  16. 16. M. M. Ghorab, H. I. Zienab, A. Mohamad and A. A. Radwan, Synthesis, antimicrobial evaluation and molecular modelling of novel sulfonamides carrying a biologically active quinazoline nucleus, J. Pharm. Res.36 (2013) 660–670; DOI: 10.1007/s12272-013-0094-6.10.1007/s12272-013-0094-623529860
  17. 17. M. M. Ghorab, H. I. Zienab, A. A. Radwan and A. Mohamad, Synthesis and pharmacophore modeling of novel quinazolines bearing a biologically active sulfonamide moiety, Acta Pharm. 63 (2013) 1–18; DOI: 10.2478/acph-2013-0006.10.2478/acph-2013-000623482309
  18. 18. M. M. Ghorab, F. A. Ragab, H. I Heiba and M. G. El-Gazzar, Synthesis, in vitro anticancer screening and radiosensitizing evaluation of some new 4-[3-(substituted)thioureido]-N-(quinoxalin-2-yl)-benzenesulfonamide derivatives, Acta Pharm.61 (2011) 415–425; DOI: 10.2478/v10007-011-0040-4.10.2478/v10007-011-0040-422202200
  19. 19. M. M. Ghorab, F. A. Ragab, H. I. Hieba, H. A. Yousef and M. G. El-Gazzar, Synthesis of novel pyrazole and pyrimidine derivatives bearing sulfonamide moiety as antitumor and radiosensitizing agents, Med. Chem. Res.21 (2012) 1376–1383; DOI: 10.1007/s00044-013-0721-210.1007/s00044-013-0721-2
  20. 20. M. S. Al-Dosari, M. M. Ghorab, M. S. Alsaid, Y. M. Nissan and A. B. Ahmed, Synthesis and anti-cancer activity of some novel trifluoromethylquinolines carrying a biologically active benzene-sulfonamide moiety, Eur. J. Med. Chem.69 (2013) 373–383; DOI: 10.1016/j.ejmech.2013.08.048.10.1016/j.ejmech.2013.08.04824077528
  21. 21. M. M. Ghorab and M. S. Alsaid, Synthesis and antitumor activity of some novel hydrazide, 1, 2-dihydropyridine, chromene, and benzochromene derivatives, J. Heterocycl. Chem.49 (2012) 272–280; DOI: 10.1002/jhet.829.10.1002/jhet.829
  22. 22. M. M. Ghorab, F. A. Ragab, H. I. Hieba and W. M. Ghorab, Design and synthesis of some novel quinoline derivatives as anticancer and radiosensitizing agents targeting VEGFR tyrosine kinase, J. Heterocycl. Chem.48 (2011) 1269–1279; DOI: 10.1002/jhet.749.10.1002/jhet.749
  23. 23. M. M. Ghorab, M. S. Alsaid and E.M. El-hossary, In vitro cytotoxic evaluation of some new heterocyclic sulfonamide derivatives, J. Heterocycl. Chem.48 (2011) 563–571; DOI: 10.1002/jhet.619.10.1002/jhet.619
  24. 24. H. Cope, R. Mutter, W. Heal, C. Pascoe, P. Brown, S. Pratt and B. Chen, Synthesis and SAR study of acridine, 2-methylquinoline and 2-phenylquinazoline analogues as anti-prion agents, Eur. J. Med. Chem.41 (2006) 1124–1143; DOI: 10.1016/j.ejmech.-2006.05.002.
  25. 25. K. Juvale, J. Gallus and M. Wiese, Investigation of quinazolines as inhibitors of breast cancer resistance protein (ABCG2), Bioorg. Med. Chem.21 (2013) 7858–7873; DOI: 10.1016/j.bmc.2013.10.007.10.1016/j.bmc.2013.10.00724184213
  26. 26. B. R. Dravyakar and P. B. Khedekar, Study of synthesis of novel N,2-diphenylquinazolin-4-amine derivatives as an anti-inflammatory and analgesic agent, Der Pharma Chem.4 (2012) 699–706.
  27. 27. J. Kapil and W. Michael, 4-Substituted-2-phenylquinazolines as inhibitors of BCRP, Bioorg. Med. Chem. Lett.22 (2012) 6766–6769; DOI: /10.1016/j.bmcl.2012.08.024.10.1016/j.bmcl.2012.08.02423017888
  28. 28. F. Ebel, A. Schuhmacher and K. E. Kling, Vat Dyes for Dyeing Fibers, Fabrics, and Other Structures Consisting of High Molecular Weight Substances Containing Carboxamide Groups, Patent DE 1046565, December 18, 1958.
  29. 29. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney and M. R. Boyd, New colorimetric cytotoxicity assay for anticancer-drug screening, J. Natl. Cancer Inst.82 (1990) 1107–1112; DOI: 10.1093/jnci/-82.13.1107.
DOI: https://doi.org/10.1515/acph-2015-0021 | Journal eISSN: 1846-9558 | Journal ISSN: 1330-0075
Language: English
Page range: 299 - 309
Accepted on: Feb 16, 2015
Published on: Sep 30, 2015
Published by: Croatian Pharmaceutical Society
In partnership with: Paradigm Publishing Services
Publication frequency: 4 issues per year
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© 2015 Mostafa M. Ghorab, Mansour S. Alsaid, published by Croatian Pharmaceutical Society
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.