Synthesis, Structural Calculations and Molecular Docking Studies of a Novel Uracil Derived Organic Molecule

Yıl 2018, Cilt: 46 Sayı: 3, 373 - 380, 01.09.2018

Gamze Koz

Öz

A novel uracil derived compound, (E)-5-((3-chloro-2-hydroxybenzylidene)amino) pyrimidine-2,4(1H,3H)-
dione, was synthesized and characterized using spectroscopic techniques. The interaction of the molecule
with DNA was explored using computational methods which revealed that the molecule could act as a groove
binder. The physicochemical properties of the molecule such as frontier molecule orbitals and chemical reactivity
parameters were also investigated. 

Anahtar Kelimeler

Uracil, Schiff base, DNA binding, groove binder, molecular modelling

Kaynakça

• G. Bischoff, S. Hoffmann, DNA-Binding of Drugs Used in Medicinal Therapies, Current Medicinal Chemistry, 9 (2002) 321-348.
• A. Hartwig, The role of DNA repair in benzene-induced carcinogenesis, Chem.-Biol. Interact., 184 (2010) 269- 272.
• G. P. Mantle, V. F. Marquis, A. R. Manderville, B. Squillaci and A. Pfohl-Leszkowicz, Structures of Covalent Adducts between DNA and Ochratoxin A: A New Factor in Debate about Genotoxicity and Human Risk Assessment, Chem. Res. Toxicol., 23 (2010) 89-98.
• S. Kashanian, S. Askari, F. Ahmadi, K. Omidfar, S. Ghobadi and A. F. Tarighat, In Vitro Study of DNA Interaction with Clodinafop-Propargyl Herbicide, DNA Cell Biol., 27 (2008) 581-586.
• A. F. Tanious, Y. D. Ding, A. D. Patrick, R. R. Tidwell and D. W. Wilson, A New Type of DNA Minor-Groove Complex: Carbazole Dication−DNA Interactions, Biochemistry, 36 (1997) 15315-15325.
• F. Ahmadi and F. Bakhshandeh, In Vitro Study of Damaging Effects of 2,4-Dichlorophenoxyacetic Acid on DNA Structure by Spectroscopic and Voltammetric Techniques, DNA Cell Biol., 28 (2009) 527-533
• R. M. Shaker, M. A. Elrady, K. U. Sadek, Synthesis, reactivity, and biological activity of 5-aminouracil and its derivatives, Mol. Divers., 20 (2016) 153-183.
• M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, Jr. J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, O. D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. AlLaham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. C. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision C.02. Gaussian, Inc.,Wallingford CT. (2004).
• A.D. Becke, Density functional thermochemistry III, The role of exact Exchange, J. Chem. Phys., 98, (1993), 5648-5652.
• R. G. Pearson, The electronic chemical potential and chemical hardness, Journal of molecular Structure: Theochem, 255 (1992) 261.
• R. G. Parr, L. Szentpaly, S. Liu, Electrophilicity Index, J. Am. Chem. Soc.,121 (1999) 1922.
• O. Trott, A. J. Olson, AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, J. Comput. Chem., 31 (2010) 455.
• Y. Kaya, V. T. Yilmaz, T. Arslan, O. Buyukgungor, Experimental and theoretical DFT studies of structure, spectroscopic and fluorescence properties of a new imine oxime derivative, Journal of Molecular Structure, 1024 (2012) 65-72.
• T. J. Beaula, P. Muthuraja, M. Sethuram, M. Dhandapani, V.K. Rastogi, V. Bena Jothy, Biological and spectral studies of O-Tolyl Biguanide: Experimental and theoretical approach, J. Mol. Struct. 1128 (2017) 290.
• R. Satheeshkumar, R. Shankar, W. Kaminsky, S. Kalaiselvi, V.V. Padma, K.J.R. Prasad, Theoretical and experimental investigations on molecular structure of 7-chloro-9-phenyl-2,3-dihydroacridin-4(1H)-one with cytotoxic studies, J. Mol. Struct. 1109 (2016) 247.
• S. Jaime-Figueroa, A. Zamilpa, A. Guzma´n, D. J. Morgans,Jr., N-3-Alkylation of uracil and derivatives via N-1-boc protection, Synthetic Communications, 31 24 (2001) 3739-3746.