A theoretical study on basicity behaviour of some 4-aminoquinazoline derivatives

Yıl 2011, Cilt: 1 Sayı: 2, 141 - 148, 12.04.2011

Funda Tay , Taner Arslan

Öz

The acidity constants (K_a) of some 6-substitue-4-aminoquinazoline compounds were investigated theoretically. The gas and aqueous phase geometries and the possible tautomeric forms were defined with full geometry optimization by using B3LYP/6-31G(d) method for 6-substitue-4-aminoquinazoline  derivatives. It was found that most stable forms are amino form and the first protonation occurs at ring nitrogen atom(N1).

Anahtar Kelimeler

Protonation, DFT calculation, aminoquinazoline derivatives, taoutomerizm

BAZI 4-AMİNOKİNAZOLİN TÜREVLERİNİN BAZLIK DAVRANIŞLARI ÜZERİNE TEORİK BİR ÇALIŞMA

Öz

Anahtar Kelimeler

Protonlanma, DFT hesaplaması, Aminokinazolin türevleri, Tautomerizm

Kaynakça

• Abouzid, K. and Shouman,S.(2008). Design, synthesis and in vitro antitumor activity of 4- aminoquinoline and 4-aminoquinazoline derivatives targeting EGFR tyrosine kinase. Bioorgan- ic& Medicinal Chemistry 16, 7543-7551.
• Alizadeh, K., Rezaei, B. and Maddah, B. (2010). Spectrophotometric determination of aqueous acidity constants of three azo dyes. Central European Journal of Chemistry 8(2), 392-395.
• Cakici, M., Catir, M., Karabuga, S., Kilic, H., Ulukanli, S., Gulluce, M. and Orhan, F. (2010). Synthe- sis and biological evaluation of (S)-4-aminoquinazoline alcohols. Tetrahedron:Asymmetry 21, 2027-2031.
• Fry, D.W., Kraker, A.J., McMichael, A., Ambroso, L.A., Nelson, J.M., Leopold, W.R., Connors, R.W. and Bridges, A.J. (1994). A spesific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science 265, 1093-1095.
• Gangjee, A., Zaveri, N., Kothare, M. and Queener, S.F. (1995). Nonclassical 2,4-diamino-6- (aminomethyl)-5, 6, 7, 8-tetrahydroquinazoline antifolates: synthesis and biological activities. Journal of Medicinal Chemistry 38, 3660-3668.
• Harris, N.V., Smith, C. and Bowden, K. (1990). Antifolate and antibacterial activities of 5-substituted 2,4-diaminoquinazolines. Journal of Medicinal Chemistry 33, 434-444.
• Hemmateenejad, B., Emami, L. and Sharghi, H. (2010). Multi-wavelength spectrophotometric deter- mination of acidity constant of some newly synthesized Schiff bases and their QSPR study. Spectrochimica Acta Part A 75, 340-346.
• Hynes, J.B., Tomazic, A., Kumar, A., Kumar, V. and Freisheim, J.H. (1991). Inhibition of human di- hydrofolate reductase by 2,4-diaminoquinazolines bearing simple substituents on the aromatic ring. Journal of Heterocyclic Chemistry 28, 1981-1986.
• Kawakami, J.K., Martinez, Y., Sasaki, B., Harris, M., Kurata, W.E. and Lau, A.F. (2011). Investiga- tion of a novel molecular descriptor for the lead optimization of 4-aminoquinazolines as vascu- lar endothelial growth factor receptor-2-inhibitors: application for quantitative structure-activity relationship analysis in lead optimization. Bioorganic& Medicinal Chemistry Letters 21 1371- 1375.
• Liu, G., Yang, S., Song, B., Xue, W., Hu, D., Jin, L. and Lu, P. (2006). Microwave assisted synthesis of N-arylheterocyclic substituted-4-aminoquinazoline derivatives. Molecules 11, 272-278.
• Liu, G. Hu, D.Y., Jin, L.H., Song, B.A., Yang, S., Liu, P.S., Bhadury, P.S., Ma, Y., Luo, H. and Zhou, X. (2007). Synthesis and bioactivities of 6,7,8-trimethoxy-N-aryl-4-aminoquinazoline deriva- tives. Bioorganic& Medicinal Chemistry 15, 6608-6617.
• McLuskey, K., Gibellini, F., Carvalho, P., Avery, M.A. and Hunter, W.N. (2004). Inhibition of Leishmania major pteridine reductase by 2,4,6- triaminoquinazoline: structure of the NADPH ternary complex. Acta Crystallographica D 60, 1780-1785.
• Myers, M.R., Setzer, N.N., Spada, A.P., Person, P.E., Ly, C.Q., Maguire, M.P., Zulli, A.L., Cheney, D.L., Zilberstein, A., Johson, S.E., Franks, C.F. and Mitchell, K.J. (1997). The synthesis and sar of phenyl)aminopyrazole [3,4-d]pyrimidines, inhibitors of CSF-1R tyrosine kinase activity. Bioor- ganic& Medicinal Chemistry Letters 7(4), 421-424. and 4-(N-alkyl-N
• Okano, M., Mito, J., Maruyama, Y., Masuda, H., Niwa, T., Nakagawa, S., Nakumura, Y. and Matsuura, A. (2009). Discovery and structure-activity relationships of 4-aminoquinazoline de- rivatives, a novel class of opioid receptor like-1 (ORL1) antagonists. Bioorganic& Medicinal Chemistry 17, 119-132.
• Rosowsky, A., Papoulis, A., Forsch, R.A. and Queener, S.F. (1999). Synthesis and antiparasitic and antitumor activity of 2,4-diamino-6-(arylmethyl)-5,6,7,8-tetrahydroquinazoline anologues of pritrexim. Journal of Medicinal Chemistry 42, 1007-1017.
• Traxler, P.M., Furet, P., Melt, H., Buchdunger, E., Meyer, T. and Lydon, N. (1996). 4- (Phenylamino)pyrrolopyrimidines: potent and selective, ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase. Journal of Medicinal Chemistry 39, 2285-2292.
• Zielinski, W. and Kudelko, A. (2000a). Concerning the basicity of 4-dimethylaminoquinazoline deri- vatives. Monatshefte für Chemie 131, 733-738.
• Zielinski, W. and Kudelko, A. (2000b). Synthesis and basicity of 4-amino-2-phenylquinazolines. Mo- natshefte für Chemie 131, 895-899.
• Zielinski, W. and Kudelko, A. (2005). Acid base interactions in some isoquinoline and quinazoline amino derivatives. Arkivoc v, 66-82.