Designing sedative/hypnotic compounds from a novel substructural graph-theoretical approach
Tóm tắt
A novel approach to computer-aided molecular design is illustrated. This approach is based on the calculation of the spectral moments of the bond adjacency matrix of graphs representing molecular structures. Spectral moments are then expressed as linear combinations of the different sub-structures present in molecules. Two series of compounds, one containing sedative/hypnotic and the other containing different classes of drugs were used to find a discriminant function with the present approach. Several compounds from the Merck Index were identified by the model as sedative/hypnotic, five of them were found in the recent literature as possessing this activity. The critical fragments, actives and inactive ones, were detected.
Tài liệu tham khảo
Lutz, M.W., Menius, J.A., Laskody, R.G., Domanico, P.L., Goetz, A.G., Saussy, D.L. and Rimele, T., Network Science, Vol. 2, Issue 9, September 1996. http:\\www.netsci.org\Science\Screening\feature05.html.
Loew, G.H., Villar, H.O. and Alkorta, Y., Pharm. Res., 10 (1993) 475.
Briggs, J.M., Marrone, T.J. and McCammon, J.A., Trends Cardiovasc. Med., 6 (1996) 198.
Wess, G., Drug Discovery Today, 1 (1996) 529.
Veerapandian, B., In Wolff, M.E. (Ed.) Burger's Medicinal Chemistry and Drug Discovery, 5th ed., John Wiley & Sons, New York, NY, 1995, pp. 303–348.
Sun, E. and Cohen, F.E., Gene, 137 (1993) 127.
Kuntz, J, D., Meng, E.C. and Shoichet, B.K., Acc. Chem. Res., 27 (1994) 117.
Jackson, R.C., Curr. Opin. Biotech., 6 (1995) 651.
Siebel, G.L. and Kollman, P.A., In Hansch, C., Sammes, P.G., Taylor, J.B. and Ramdsen, C.A. (Eds.) Comprehensive Medicinal Chemistry. Vol. 4. Quantitative Drug Design, Pergamon, 1990, pp. 125–138.
Bowen, J.P. and Allinger, N.L., In Lipkowitz, K.B. and Boyd, D.B. (Eds.) Reviews in Computational Chemistry, Vol. 2, VCH, 1991, pp. 81–97.
Weinstein, H., Osman, R and Green, J.P., In Olson, E.C. and Christoffersen, R.E. (Eds.) Computer-Assisted Drug Design, ACS Symp. Ser., 112, 1979, pp. 161–170.
Johnson, M.A. and Maggiora, G.M. (Eds.) Concepts and Applications of Molecular Similarity, John Wiley Intersciences, New York, NY, 1990.
Heller, S.R., J. Chem. Inf. Comput. Sci., 32 (1992) 578.
Hall, L.H. and Kier L.B., In Lipkowitz, K.B. and Boyd, D.B. (Eds.) Reviews in Computational Chemistry. Vol. 1, VCH, 1991, pp. 367–422.
Bersuker, Y.B. and Dimoglio, A.S., In Lipkowitz, K.B. and Boyd, D.B. (Eds.) Reviews in Computational Chemistry, Vol 1, VCH, 1991, pp. 423–479.
Basak, S.C., Grunwald, G.D. and Niemi, G.I. In Balaban, A.T. (Ed.) From Chemical Topology to three-Dimensional Geometry, Plenum Press, New York, NY, 1997, pp. 73–116.
Gálvez, J. and García-Domenech, R., In Mosqueira, A. (Ed.) Diseño de Medicamentos, Farmaindustria, Madrid, 1994, pp. 357–392.
Hansch, C. and Klein, T.E., Acc. Chem. Res., 19 (1986) 392.
Fujita, T., In Hansch, C., Sammes, P.G., Taylor, J.B. and Ramdsen, C.A. (Eds.) Comprehensive Medicinal Chemistry. Vol. 4. Quantitative Drug Design, Pergamon, 1990, pp. 497–560.
Martin, Y.C., Bures, M.G., Danaher, E.A., Delazzer, J., Lico, I. and Pavlik, P.A., J. Comput.-Aided Mol. Design, 7 (1993) 83.
Kaminski, J.J., Adv. Drug Delivery Rev., 14 (1994) 331.
Cramer III, R.D., Patterson, D.E. and Bunce, J.D., J. Am. Chem. Soc., 110 (1988) 5959.
Kellogg, G., Kier, L.B., Gaillard, P. and Hall, L., J. Comput.-Aided Mol. Design, 10 (1997) 513.
Kubinyi, H., In Hansch, C., Sammes, P.G., Taylor, J.B. and Ramdsen, C.A. (Eds.) Comprehensive Medicinal Chemistry. Vol. 4. Quantitative Drug Design, Pergamon, 1990, pp. 589–643.
Smolenskii, G.A., Zh. Fiz. Khim., 38 (1964) 1288.
Klein, D.J., Int. J. Quantum Chem.: Quantum Chem. Symp., 20 (1986) 153.
McHughes, M.C. and Poshusta, M.C., J. Math. Chem., 4 (1990) 227.
Estrada, E., J. Chem. Inf. Comput. Sci., 36 (1996) 844.
Estrada, E., J. Chem. Inf. Comput. Sci., 37 (1997) 320.
Estrada, E., J. Chem. Inf. Comput. Sci., 38 (1998) 27.
Estrada, E., J. Chem. Inf. Comput. Sci., 35 (1995) 31.
Estrada, E., J. Chem. Inf. Comput. Sci., 35 (1995) 701.
Estrada, E. and Ramírez, A., J. Chem. Inf. Comput. Sci., 36 (1996) 837.
Estrada, E., J. Chem. Soc. Faraday Trans., 94 (1998) 1407.
Gutierrez, Y. and Estrada, E., TOSS-MODE for Windows' 95, version 3.0. Universidad Central de Las Villas, Santa Clara, Cuba, 1997.
Gálvez, J., García-Domenech, R., De Julian-Ortiz, J.V. and Soler, R., J. Chem. Inf. Comput. Sci., 35 (1995) 272.
Gálvez, J., García-Domenech, R., De Julian-Ortiz, J.V. and Soler, R., J. Chem. Inf. Comput. Sci., 34 (1994) 1198.
García Domenech, R., García-Mareh, F. J., Soler, R., Gálvez, J., Antón-Fos, G.M. and De Julián-Ortiz, J. V., Quant. Struct.-Act. Relat., 15 (1996) 201.
Gálvez, J., García-Domenech, R., De Gregorio-Alapont, C., De Julián-Ortiz, J.V. and Popa, L., J. Mol. Graphics, 14 (1996) 272.
García-Domenech, R., De Gregorio-Alapont, C., De Julián-Ortiz, V., Gálvez, J. and Popa, L., Bioorg. Med. Chem. Lett., 7 (1997) 567.
STATISTICA version 4.13, Statsoft, Inc. (1993).
Ortiz-de-Urbina, A.V., Martin, M.L., Montero M. J., Moran, A. and San-Roman, L., J. Ethnopharmacol., 25 (1989) 165.
De Luca, C. and Massotti, M., Prog. Neuropsychopharmacol. Biol. Psychiatry, 14 (1990) 597.
The Merck Index 11th Edition, Merck & Co., Inc., New York, NY, 1989.
Tzischinsky, O., Sleep, 17 (1994) 638.
Klotz, W., Anaesthesiol. Reanim., 14 (1989) 347.
Levine, R.L., Crit. Care Clin., 10 (1994) 709.
Gerwels, J.W., Bezzant, J.L., Le Mariel, L., Pauley, L.F. and Streisand, J.B., J. Dermatol. Surg. Oncol., 20 (1994) 823.
Freye, G., Latasch, L., Schmidhommey, H. and Portoghese, P., Anaesthesist., 43 (1994) Suppl. 2, 552.
PCMODEL. Serena Software: Bloomington, USA.
Franke, R. Theoretical Drug Design Methods, Elsevier, Amsterdam, 1984.