Summary
In this paper we propose theoretical models for the conformations of triacetonamine and protonated triacetonamine (Vincubine, an anticancer chemotherapeutic agent) developed by quantum and molecular mechanics techniques. We discuss the theoretical factors which are involved in the stabilization of the conformations calculated by the MNDO, MM2 and COPEANE methods and show the relative percent abundance of each molecular shape. Graphic representations of the conformers are depicted.
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References
Boyd, D.B., Drug Inf. J., 17 (1983) 121.
Montero, L.A., La quimica computacional en Cuba. In II. Congreso de la Sociedad Cubana de Quimica, Santiago de Cuba, 1985, p. 34.
Momany, F.A., Carruthers, L.M., McGuire, R.F. and Scheraga, H.A., J. Phys. Chem., 78 (1974) 1595.
Allinger, N.L., Adv. Phys. Org. Chem., 13 (1976) 1.
Allinger, N.L., J. Am. Chem. Soc., 99 (1977) 8127.
Montero, L.A., Alvarez, J.R., del Bosque, J.R., Gonz lez, M.C., Cano, R. and Rodriguez, M.C., Folia Chim. Theor. Lat., (1988) 33.
Testa, B., Principles of Organic Stereochemistry, Marcel Dekker, New York, Basel, 1979, p. 217.
Blackburne, I.D., Katritzky, A.R. and Takeuchi, Y., Acc. Chem. Res., 8 (1975) 300.
Bocourt, R., Eliel, E.L. and Allinger, N.L. (Eds.) Topics in Stereochemistry, Vol. 8, Wiley, New York, NY, 1974, pp. 159–224.
Cuéllar, A. and O'Farrill, H., Rev. Cub. Farm., 9 (1975) 151.
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Navajas, C.C., Montero, L.A. & La Serna, B. Theoretical models for the conformations and the protonation of triacetonamine. J Computer-Aided Mol Des 4, 403–409 (1990). https://doi.org/10.1007/BF00117405
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DOI: https://doi.org/10.1007/BF00117405