One-pot Three-component Synthesis of Novel Quinazoline-4-carboxylic Acid and Derivatives

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.

Keywords

• Quinazoline-4-carboxylic acid,isatin,ester,amide

References

1. 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. 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. 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. 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. 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. 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. 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. 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. 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. 10. M.S. Malamas, J. Millen, Quinazolineacetic Acids and Related Analogs as Aldose Reductase Inhibitors, J Med Chem, 34 (1991) 1492-1503.
11. 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. 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. 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. 14. R.S. Herbst, Erlotinib (Tarceva): an update on the clinical trial program, Semin Oncol, 30 (2003) 34-46.
15. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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.