One-pot Three-component Synthesis of Novel Quinazoline-4-carboxylic Acid and Derivatives
Year 2020,
Volume: 48 Issue: 3, 283 - 290, 15.06.2020
Derviş Gök
Abstract
Amonyum asetat ve benzaldehit ile isatinin hidrolizinden elde edilen (2-amino-fenil)-okso-asetik asit sodyum tuzunun aynı ortamda üç bileşenli reaksiyonundan 2-fenil-kinazolin-4-karboksilik asit (2) sentezlendi. Daha sonra 2 ve çeşitli alkoller arasındaki reaksiyonlarından bazı yeni kinazolin-ester türevleri (3a-d) elde edildi. Son olarak 2 bileşiği ile SOCl2’nin reaksiyonundan elde edilen 2-fenil-kinazolin-4-karbonil klorür ve çeşitli aminlerin reaksiyonundan kinazolin-amit türevleri (5a-e) sentezlendi. Sentezlenen bileşiklerin yapıları 1H NMR, 13C NMR, IR, kütle spektrometri analiz metotları tarafından doğrulandı.
Supporting Institution
Dumlupinar University Technology Research Fund
Thanks
We are grateful to the Dumlupinar University Technology Research Fund for the financial support of this study through project number of 2015/24.
References
- 1. H.M. Shallal, W.A. Russu, Discovery, synthesis, and investigation of the antitumor activity of novel piperazinylpyrimidine derivatives, Eur J Med Chem, 46 (2011) 2043-2057.
- 2. G. Grover, S.G. Kini, Synthesis and evaluation of new quinazolone derivatives of nalidixic acid as potential antibacterial and antifungal agents, Eur J Med Chem, 41 (2006) 256-262.
- 3. A.B.A. El-Gazzar, M.M. Youssef, A.M.S. Youssef, A.A. Abu-Hashem, F.A. Badria, Design and synthesis of azolopyrimidoquinolines, pyrimidoquinazolines as anti-oxidant, anti-inflammatory and analgesic activities, Eur J Med Chem, 44 (2009) 609-624.
- 4. P. Verhaeghe, N. Azas, M. Gasquet, S. Hutter, C. Ducros, M. Laget, S. Rault, P. Rathelot, P. Vanelle, Synthesis and antiplasmodial activity of new 4-aryl-2-trichloromethylquinazolines, Bioorg Med Chem Lett, 18 (2008) 396-401.
- 5. R.A. Smits, M. Adami, E.P. Istyastono, O.P. Zuiderveld, C.M.E. van Dam, F.J.J. de Kanter, A. Jongejan, G. Coruzzi, R. Leurs, I.J.P. de Esch, Synthesis and QSAR of Quinazoline Sulfonamides As Highly Potent Human Histamine H-4 Receptor Inverse Agonists, J Med Chem, 53 (2010) 2390-2400.
- 6. C. Mendoza-Martinez, J. Correa-Basurto, R. Nieto-Meneses, A. Marquez-Navarro, R. Aguilar-Suarez, M.D. Montero-Cortes, B. Nogueda-Torres, E. Suarez-Contreras, N. Galindo-Sevilla, A. Rojas-Rojas, A. Rodriguez-Lezama, F. Hernandez-Luis, Design, synthesis and biological evaluation of quinazoline derivatives as anti-trypanosomatid and anti-plasmodial agents, Eur J Med Chem, 96 (2015) 296-307.
- 7. T. Herget, M. Freitag, M. Morbitzer, R. Kupfer, T. Stamminger, M. Marschall, Novel chemical class of pUL97 protein kinase-specific inhibitors with strong anticytomegaloviral activity, Antimicrob Agents Ch, 48 (2004) 4154-4162.
- 8. T.P. Selvam, P.V. Kumar, A.S. Kumar, I.A. Emerson, Study of inhibitory mechanism and binding mode of the thiazolo quinazoline compounds to HIV-1 integrase by docking, J Pharm Res, 3 (2010) 1637–1647.
- 9. S.K. Kashaw, V. Kashaw, P. Mishra, N.K. Jain, J.P. Stables, Synthesis, anticonvulsant and CNS depressant activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea, Eur J Med Chem, 44 (2009) 4335-4343.
- 10. M.S. Malamas, J. Millen, Quinazolineacetic Acids and Related Analogs as Aldose Reductase Inhibitors, J Med Chem, 34 (1991) 1492-1503.
- 11. J.P. Xu, X.Y. Liu, S. Yang, C.G. Zhang, L. Wang, Y.K. Shi, Icotinib as initial treatment in lung adenocarcinoma patients with brain metastases, Thorac Cancer, 7 (2016) 437-441.
- 12. D. Cameron, M. Casey, M. Press, D. Lindquist, T. Pienkowski, C.G. Romieu, S. Chan, A. Jagiello-Gruszfeld, B. Kaufman, J. Crown, A. Chan, M. Campone, P. Viens, N. Davidson, V. Gorbounova, J.I. Raats, D. Skarlos, B. Newstat, D. Roychowdhury, P. Paoletti, C. Oliva, S. Rubin, S. Stein, C.E. Geyer, A phase III randomized comparison of lapatinib plus capecitabine versus capecitabine alone in women with advanced breast cancer that has progressed on trastuzumab: updated efficacy and biomarker analyses, Breast Cancer Res Treat, 112 (2008) 533-543.
- 13. R.N. Brogden, R.C. Heel, T.M. Speight, G.S. Avery, Prazosin: a review of its pharmacological properties and therapeutic efficacy in hypertension, Drugs, 14 (1977) 163-197.
- 14. R.S. Herbst, Erlotinib (Tarceva): an update on the clinical trial program, Semin Oncol, 30 (2003) 34-46.
- 15. M. Murphy, B. Stordal, Erlotinib or gefitinib for the treatment of relapsed platinum pretreated non-small cell lung cancer and ovarian cancer: a systematic review, Drug Resist Updat, 14 (2011) 177-190.
- 16. G.M. Chinigo, M. Paige, S. Grindrod, E. Hamel, S. Dakshanamurthy, M. Chruszcz, W. Minor, M.L. Brown, Asymmetric synthesis of 2,3-dihydro-2-arylquinazolin-4-ones: methodology and application to a potent fluorescent tubulin inhibitor with anticancer activity, J Med Chem, 51 (2008) 4620-4631.
- 17. T. Sardon, T. Cottin, J. Xu, A. Giannis, I. Vernos, Development and biological evaluation of a novel aurora A kinase inhibitor, Chembiochem, 10 (2009) 464-478.
- 18. S.L. Cao, Y. Wang, L. Zhu, J. Liao, Y.W. Guo, L.L. Chen, H.Q. Liu, X. Xu, Synthesis and cytotoxic activity of N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates, Eur J Med Chem, 45 (2010) 3850-3857.
- 19. D.W. Fry, A.J. Kraker, A. McMichael, L.A. Ambroso, J.M. Nelson, W.R. Leopold, R.W. Connors, A.J. Bridges, A specific inhibitor of the epidermal growth factor receptor tyrosine kinase, Science, 265 (1994) 1093-1095.
- 20. N. Malecki, P. Carato, B. Rigo, J.F. Goossens, R. Houssin, C. Bailly, J.P. Henichart, Synthesis of condensed quinolines and quinazolines as DNA ligands, Bioorgan Med Chem, 12 (2004) 641-647.
- 21. H.N. Seo, J.Y. Choi, Y.J. Choe, Y. Kim, H. Rhim, S.H. Lee, J. Kim, D.J. Joo, J.Y. Lee, Discovery of potent T-type calcium channel blocker, Bioorg Med Chem Lett, 17 (2007) 5740-5743.
- 22. W. Zhang, F. Guo, F. Wang, N. Zhao, L. Liu, J. Li, Z.H. Wang, Synthesis of quinazolines via CuO nanoparticles catalyzed aerobic oxidative coupling of aromatic alcohols and amidines, Org Biomol Chem, 12 (2014) 5752-5756.
- 23. C. Huang, Y. Fu, H. Fu, Y.Y. Jiang, Y.F. Zhao, Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives, Chem Commun, (2008) 6333-6335.
- 24. C.C. Malakar, A. Baskakova, J. Conrad, U. Beifuss, Copper-Catalyzed Synthesis of Quinazolines in Water Starting from o-Bromobenzylbromides and Benzamidines, Chem-Eur J, 18 (2012) 8882-8885.
- 25. R. Alonso, A. Caballero, P.J. Campos, D. Sampedro, M.A. Rodriguez, An efficient synthesis of quinazolines: a theoretical and experimental study on the photochemistry of oxime derivatives, Tetrahedron, 66 (2010) 4469-4473.
- 26. Y. Ohta, Y. Tokimizu, S. Oishi, N. Fujii, H. Ohno, Direct Synthesis of Quinazolines through Copper-Catalyzed Reaction of Aniline-Derived Benzamidines, Org Lett, 12 (2010) 3963-3965.
- 27. Z.H. Zhang, X.N. Zhang, L.P. Mo, Y.X. Li, F.P. Ma, Catalyst-free synthesis of quinazoline derivatives using low melting sugar-urea-salt mixture as a solvent, Green Chem, 14 (2012) 1502-1506.
- 28. F. Portela-Cubillo, J.S. Scott, J.C. Walton, Microwave-Promoted Syntheses of Quinazolines and Dihydroquinazolines from 2-Aminoarylalkanone O-Phenyl Oximes, J Org Chem, 74 (2009) 4934-4942.
- 29. J.T. Zhang, D.P. Zhu, C.M. Yu, C.F. Wan, Z.Y. Wang, A Simple and Efficient Approach to the Synthesis of 2-Phenylquinazolines via sp(3) C-H Functionalization, Org Lett, 12 (2010) 2841-2843.
- 30. C. Derabli, R. Boulcina, G. Kirsch, B. Carboni, A. Debache, A DMAP-catalyzed mild and efficient synthesis of 1,2-dihydroquinazolines via a one-pot three-component protocol, Tetrahedron Lett, 55 (2014) 200-204.