Synthesis of anticonvulsant sulfamides. Theoretical study of the related mechanism

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A theoretical study of the mechanisms associated with the synthesis of anticonvulsant symmetric A,N′-substituted sulfamides is presented. Two possible synthetic routes are compared, which mainly differ in the use of pyridine as a nucleophilic agent in the reaction mechanism. Geometry optimization te...

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Autor principal: Gavernet, L.
Otros Autores: Cisneros, H.S, Bruno-Blanch, L.E, Estiú, G.L
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Springer New York 2003
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 cas  |a pyrimidine, 289-95-2 
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100 1 |a Gavernet, L. 
245 1 0 |a Synthesis of anticonvulsant sulfamides. Theoretical study of the related mechanism 
260 |b Springer New York  |c 2003 
270 1 0 |m Estiú, G.L.; Depto. Quim. Inorg., Analitica Q., Fac. de Ciencias Exactas y Naturales, Ciudad UniversitariaArgentina; email: estiu@biol.unlp.edu.ar 
506 |2 openaire  |e Política editorial 
504 |a Supuran, C.T., Scozzafava, A., (2002) Exp Opin Ther Pat, 12, p. 217 
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504 |a Abbate, F., Supuran, C., Scozzafava, A., Orioli, P., Stubbs, M., Klebe, G., (2002) J Med Chem, 45, p. 3583 
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504 |a Supuran, C.T., Scozzafava, A., (2001) Curr Med Chem Imm Endoc Metab Agents, 1, p. 61 
504 |a Dougherty, J.M., Probs, D.A., Robinson, R.E., Moore, J.D., Klein, T.A., Snelgrove, K.A., Hanson, P.R., (2000) Tetrahedron, 56, p. 9781 
504 |a Acheson, R.M., Bite, M.G., Kemp, J.E.G., (1981) J Med Chem, 24, p. 1300 
504 |a Castro, J.L., Baker, R., Giublin, A.R., Hobbs, S.C., Jenkins, M.R., Rusell, M.G.N., Beer, M.S., Hargreaves, R.J., (1994) J Med Chem, 37, p. 3032 
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504 |a Gong, B., Zheng, C., Skrzypczak-Jankun, E., Yan, Y., Zhang, J., (1999) J Am Chem Soc, 121, p. 9766 
504 |a Hof, F., Nuckolls, C., Rebek, J., (2000) J Am Chem Soc, 122, p. 4251. , and references therein 
504 |a Chufan, E.E., Pedregosa, J.C., Baldini, O.A., Bruno-Blanch, L., (1999) Farmaco, 54, p. 838 
504 |a Estiú, G.L., Bruno-Blanch, L.E., (2002) Biological Applications of the Quantum Chemistry Theory, , Kubli-Garfias C (ed). Research Signpost, Trivandum, India, pp 
504 |a Patani, G.A., LaVoie, E.J., (1996) Chem Rev, 96, p. 3147 
504 |a Tasso, S., Moon, S.Y., Bruno-Blanch, L.E., Estiú, G.L., submitted; Tasso, S., Bruno-Blanch, L., Estiú, G.L., (2001) J Mol Model, 7, p. 231 
504 |a Ohme, R., Preuschhof, H., (1968) Liebigs Ann Chem, 713, p. 74 
504 |a Bermann, M., Van Wazer, J.R., (1972) Synthesis, 10, p. 576 
504 |a Gong, B., Zheng, C., Skrzpczak-Jankun, E., Yan, Y., Zhang, J., (1998) J Am Chem Soc, 120, p. 11194 
504 |a Gavernet, L., Dominguez Cabrera, J., Estiú, G.L., Bruno-Blanch, L., submitted; Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pople, J.A., (1998) Gaussian 98, Revision A.9, , Gaussian, Pittsburgh, PA 
504 |a Peng, C., Ayala, P.Y., Schlegel, H.B., Frisch, M.J., (1996) J Comput Chem, 17, p. 49 
504 |a Peng, C., Schlegel, H.B., (1994) Isr J Chem, 33, p. 449 
504 |a Foresman, J.B., Keith, T.A., Wiberg, K.B., Snoonian, J., Frisch, M.J., (1996) J Phys Chem, 100, p. 16098 
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520 3 |a A theoretical study of the mechanisms associated with the synthesis of anticonvulsant symmetric A,N′-substituted sulfamides is presented. Two possible synthetic routes are compared, which mainly differ in the use of pyridine as a nucleophilic agent in the reaction mechanism. Geometry optimization techniques and transition-state detection at the B3LYP/6-31G** level, modeling the solvent by means of an isodensity polarizable continuum approach, allow the most suitable method for the experimental process to be discerned.  |l eng 
593 |a Química Medicinal, Depto. de Ciencias Biológicas, Universidad Nacional de La Plata, 1900, La Plata, Argentina 
593 |a Depto. Quim. Inorg., Analitica Q., Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, Buenos Aires, C1428EHA, Argentina 
593 |a Cequinor, Departamento de Química, Univ. Nacional de La Plata 47 y 115, La Plata, B1900AVV, Argentina 
690 1 0 |a ANTICONVULSANT SULFAMIDES 
690 1 0 |a DENSITY FUNCTIONAL CALCULATIONS 
690 1 0 |a REACTION MECHANISMS 
690 1 0 |a ANTICONVULSIVE AGENT 
690 1 0 |a PYRIMIDINE 
690 1 0 |a SOLVENT 
690 1 0 |a SULFAMIDE DERIVATIVE 
690 1 0 |a ANTICONVULSANT ACTIVITY 
690 1 0 |a CHEMICAL REACTION 
690 1 0 |a CONFERENCE PAPER 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a MODEL 
690 1 0 |a SUBSTITUTION REACTION 
690 1 0 |a THEORY 
700 1 |a Cisneros, H.S. 
700 1 |a Bruno-Blanch, L.E. 
700 1 |a Estiú, G.L. 
773 0 |d Springer New York, 2003  |g v. 110  |h pp. 434-440  |k n. 6  |p Theor. Chem. Acc.  |x 1432881X  |w (AR-BaUEN)CENRE-7026  |t Theoretical Chemistry Accounts 
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856 4 0 |u https://doi.org/10.1007/s00214-003-0499-2  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_1432881X_v110_n6_p434_Gavernet  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1432881X_v110_n6_p434_Gavernet  |y Registro en la Biblioteca Digital 
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963 |a VARI 
999 |c 65722 

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