Synthesis of 2-Methyl -3,4,5,10-Tetrahydro-Pyrrolo [3,2-A] Carbazole-Ethyl Carboxylate Derivatives and Evaluation of their Binding Affinity with CT-DNA
J. Environ. Nanotechnol. Volume 2, No.4 (2013) pp.62-67
A new class of heterocyclic compound, substituted 2-methyl-3,4,5,10-tetarahydro-pyrrolo[3,2- a]carbazole-1-ethyl carboxylate derivatives have been prepared from 1-oxo-1,2,3,4,-tetrahydrocarbazoles. The structural features were determined by analytical and spectral techniques. DNA binding study of the compounds was investigated by absorption titration experiments which indicated that the compounds showed good binding affinity to CT-DNA via intercalation.
Auclair, C., Multimodal action of antitumor agents on DNA: The ellipticine series, Arch. Biochem. Biophys.,1, 259112:1-14(1987).
Jain, S. C., Bhandary, K. K., Sobbell, H. M., Visualization of drug—nucleic acid interactions at atomic resolution. VI. Structure of two drug—dinucleoside monophosphate crystalline complexes, ellipticine—5-iodocytidylyy (3'-5') guanosine and 3,5,6,8-tetramethyl-Nmethyl phenanthrolinium—5-iodocytidylyl (3'-5') guanosine, J. Mol. Biol.,135, 813-84(1979).
Monnot, M., Mauffret, O., Simon, V., Lescot, E., Psaume, B., Saucier, J. M., DNA-drug recognition and effects on topoisomerase II-mediated cytotoxicity. A three-mode binding model for ellipticine derivatives., J. Biol. Chem.,25, 1820-1829(1991).
Singh, M. P., Hill, G. C., Peoch, D., Rayner, B., Inabach, J. L., Lown, J. W., High-Field NMR and Restrained Molecular Modeling Studies on a DNA Heteroduplex Containing a Modified Apurinic Abasic Site in the Form of Covalently Linked 9-Aminoellipticine, Biochemistry., 33, 10271-10285(1994).
Viji, M., Nagarajan, R., RuCl3/SnCl2 mediated synthesis of pyrrolo[2,3-c]carbazoles and consequent preparation of indolo[2,3-c]carbazoles, Tetrahedron., 68, 2453-2458(2012).
Vogel, A. I., Text book of practical organic chemistry,Longman, London, (1989).
Wolfe, A., Shimer, G. H., Meehan, T., Polycyclic aromatic hydrocar bons physically intercalate into duplex regions of denatured DNA, Biochemistry., 26, 6392-6396(1987).
Yamuna, E., Ajay Kumar, R., Zellar, M., Rajandra Prasad, K. J., Synthesis, antimicrobial, antimycobacterial and structure–activity relationship of substituted pyrazolo-, isoxazolo-, pyrimidoand mercaptopyrimido cyclohepta [b]indoles, Eur. J. Med. Chem.,47, 228-238(2012).
Yamuna, E., Zellar, M., Rajandra Prasad, K. J., Syntheses of indolo [3,2,1-d,e] phenanthridines and isochromeno[3,4-a] carbazoles: palladium catalyzed intramolecular arylation via C–H functionalization, Tetrahedron.,52, 6030-6034(2011).