Application of a mathematical topological pattern of antihistaminic activity for the selection of new drug candidates and pharmacology assays

Journal of Medicinal Chemistry

Volumn 49, Issue 12, 2006, Pages 3667-3673

  Duart, María J ^a   García Domenech, Ramón ^b   Gálvez, Jorge ^b   Alemán, Pedro A ^c   Martín Algarra, Rafael V ^c   Antón Fos, Gerardo M ^c  

^a MIGUEL HERNÁNDEZ UNIVERSITY   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

^c UNIVERSIDAD CEU CARDENAL HERRERA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 (DIBENZYLAMINO) 3 PHENYL 1 PROPANOL; 2 ETHYL 9,10 DIMETHOXYANTHRACENE; 2,4 BIS(ALPHA,ALPHA DIMETHYLBENZYL)PHENOL; 4 [2 (1,3 BENZOTHIAZOL 2 YL)VINYL] N,N DIMETHYLANILINE; AMFEBUTAMONE; ANALGESIC AGENT; ANILINE DERIVATIVE; ANTHRACENE DERIVATIVE; ANTIDEPRESSANT AGENT; ANTIFUNGAL AGENT; ANTIHISTAMINIC AGENT; ANTIPARKINSON AGENT; ANTITUSSIVE AGENT; BENZOTHIAZOLE DERIVATIVE; BENZYL CHLORIDE; DRUG VEHICLE; FENTANYL; HISTAMINE; MICONAZOLE; N BENZYLQUININIUM CHLORIDE; NEUROLEPTIC AGENT; NEW DRUG; NOOTROPIC AGENT; PERGOLIDE; PHENOL DERIVATIVE; PROPANOL; REAGENT; TERFENADINE; TRIHEXYPHENIDYL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DATA BASE; DRUG CLASSIFICATION; DRUG DETERMINATION; DRUG IDENTIFICATION; DRUG INFORMATION; DRUG STRUCTURE; FEMALE; MATHEMATICAL MODEL; NONHUMAN; RAT; SEDATION;

ANILINE COMPOUNDS; ANIMALS; ANTHRACENES; BENZOTHIAZOLES; DATABASES, FACTUAL; DERMATITIS; DRUG DESIGN; FEMALE; HISTAMINE; HISTAMINE H1 ANTAGONISTS; HYPNOTICS AND SEDATIVES; LINEAR MODELS; MATHEMATICS; PHENOLS; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP; TERFENADINE;

EID: 33745170023     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0580555     Document Type: Article

References (35)

1. Galvez, J.; Garcia, R.; Julian-Ortiz, J. V. de; Soler, R. Topological approach to drug design. J. Chem. Inf. Compul. Sci. 1995, 35, 272-284.
2. Roy, K.; Leonard, J. T. QSAR modeling of HIV-1 reverse transcriptase inhibitor 2-amino-6-arylsulfonylbenzonitriles and congeners using molecular connectivity and E-state parameters. Bioorg. Med. Chem. 2004, 12, 745-754.
3. Basak, S. C; Mills, D. R.; Balaban, A. T.; Gute, B. D. Prediction of mutagenicity of aromatic and heteroaromatic amines from structure: a hierarchical QSAR approach. J. Chem. Inf. Comput. Sci. 2001, 41, 671-678.
4. Golbraikh, A.; Bonchev, D.; Tropsha, A. Novel ZE-isomerism descriptors derived from molecular topology and their application to QSAR analysis. J. Chem. Inf. Comput Sci. 2002, 42, 769-787.
5. Rios-Santamarina, I.; Garcia-Domenech, R.; Galvez, J.; Morcillo Esteban, J.; Santamaria, P.; Cortijo, J. Getting new bronchodilator compounds from molecular topology. Eur. J. Pharm. Sci. 2004, 22, 271-277.
6. Hall, L. M.; Hall, L. H.; Kier, L. B. QSAR modeling of beta-lactam binding to human serum proteins. J. Comput.-Aided Mol. Des. 2003, 17, 103-118.
7. Siebel, G. L.; Kollman, P. A. Comprehensive Medicinal Chemistry: Quantitative Drug Design: Hansch, C., Sammes, P. G., Taylor, J. B., Ramdsen, C. A., Eds.; Pergamon: New York, 1990; Vol. IV, pp 125-138.
8. Weinstein, H.; Osman, R.; Green, J. P.; Olson, E. C.; Cristoffersen, R. E. Computer-Assisted Drug Design; ACS Symposium Series; American Chemical Society: Washington, DC, 1979; pp 161-170.
9. Johnson, M. A.; Maggiora, G. M. Concepts and Applications of Molecular Similarity; John Wiley-Intersciences: New York, 1990.
10. Hall, L. H.; Kier, L. B. Reviews in Computational Chemistry; Kipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishers: New York, 1991; Vol. I, pp 367-422.
11. Julián-Ortiz, J. V.; Gálvez, J.; Muñoz-Collado, C.; Garcáa-Domenech, R.; Gimeno-Cardona, C. Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds. J. Med. Chem. 1999, 42, 3308-3314.
12. Basak, S. C.; Grunwald, G. D.; Niemi, G. I. Chemical Topology to Three-Dimensional Geometry; Balaban, A. T., Eds.; Plenum Press: New York, 1997: pp 73-116.
13. Estrada, E.; Pena, P.; Garcia-Domenech, R. Designing sedative/hypnotic compounds from a novel substructural graph-theoretical approach. J. Comput.-Aided Mol. Des. 1998, 12, 583-595.
14. Hardman, J. G.; Limbird, L. E.; Molinoff, P. B.; Ruddon, R. W.; Goodman, A. Las bases Farmacológicas de la Terapeútica (The Pharmalogical Basis of Therapeutics), 9th ed.; McGraw-Hill Interamericana: Mexico, 1996; Vol. I.
15. Duart, M. J.; García-Doménech, R.; Anton-Fos, G. M.; Gálvez, J. Optimization of a mathematical topological pattern for the prediction of antihistaminic activity. J. Comput.-Aided Mol. Des. 2001, 15, 561-572.
16. Duart, M. J.; Anton-Fos, G. M.; Alemán, P. A.; Gay-Roig, J. B.; González-Rosende, M. E.; Gálvez, J.; García- Doménech, R. New potential antihistaminic compounds. Virtual combinatorial chemistry, computational screening, real synthesis, and pharmacological evaluation. J. Med. Chem. 2005, 48, 1260-1264.
17. Duart, M. J.; Antón-Fos, G. M.; Gálvez, J.; García-Domenech, R. Use of molecular topology for the prediction of the sedative effect of a group of antihistaminic drugs. Chem.-Indian J. 2003, 1, 67-75.
18. Kier, L. B.; Hall, L. H. General definition of valence delta-values for molecular connectivity. J. Pharm. Sci. 1983, 72, 1170-1173.
19. Gálvez, J.; Garcia-Domenech, R.; Salabert, M. T.; Soler, R. Charge indexes. New topological descriptors. J. Chem. Inf. Comput. Sci. 1994, 34, 520-525.
20. Kier, L. B.; Hall, L. M. An electrotopological-state index for atoms in molecules. Pharm. Res. 1990, 7, 801-807.
21. Moliner, R.; Garcia, F.; Galvez, J.; Garcia-Domenech, R.; Serrano, C. Nuevos índices topológicos en conectividad molecular. Su aplicación a algunas propiedades fisicoquímicas de un grupo de hidrocarburos alifáticos (New topological indices of molecular connectivity. Its application to some physicochemical properties of an aliphatic hydrocarbon group). An. R. Acad. Farm. 1991, 57, 287-298.
22. Shannon, C. E. A mathemathical theory of communication. Bell. Syst. Tech. J. 1948, 27, 229-235.
23. García-Domenech, R. DESMOLII Software; Unidad de Investigación de Diseño de Fármacos y Conectividad Molecular, Facultad de Farmacia, Universität de Valencia: Valencia, Spain.
24. Hall, L. H. Molconn-Z, version 3.0; Eastern Nazarene College: Quincy, MA.
25. Hocking, R. R. Criteria for selection of a subset regression: which one should be used? Technometrics 1972, 14, 967-970.
26. Cooley, W. W.; Lohnes, P. R. Multivariate Data Analysis; John Wiley & Sons: New York, 1971.
27. Allen, D. M. The relationship between variable selection and data augmentation and a method for prediction. Technometrics 1974, 16, 125-127.
28. Gálvez, J.; García-Domenech, R.; de Gregorio Alapont, C.; de Julián-Ortiz, V. J.; Popa, L. Pharmacological distribution diagrams: A tool for de novo drug design. J. Mol. Graphics 1996, 14, 272-276.
29. Woodward, J. K. Pharmacology of antihistamines. J. Allergy Clin. Immunol. 1990, 86, 606-612.
30. Estelle, F. R.; Simons, M. D. Evolution of H1-receptor antagonist treatment. Ann. Allergy 1993, 71, 282-287.
31. Peggs, J. F.; Shimp, L. A. Antihistamines: The old and the new. Am. Fam. Physician 1995, 52, 593-600.
32. Hall, L. H.; Ogren, S. O. Effects of antidepressant drugs on histamine-H1 receptors in the brain. Life Sci. 1984, 34, 597-605.
33. Svestka, J. Antidepressives of the 3rd, 4th and 5th generation. Cesk. Psychiatr. 1994, 90, 3-19.
34. Van den Berg, A. A.; Honjol, N. M.; Prabhu, N. V.; Datta, S.; Rozario, C. J.; Muraleedaran, R.; Savva, D. Analgesics and ENT surgery. A clinical comparison of the intraoperative, recovery and postoperative effects of buprenorphine, diclofenac, fentanyl, morphine, nalbuphine, pethidine and placebo given intravenously with induction of anaesthesia. Br. J. Clin. Pharmacol. 1994, 38 (6), 533-543.
35. Watanabe, K.; Nakagawa, H.; Tsurufuji, S. A new sensitive fluorimetric method for measurement of plasma exudation in the inflammatory skin reaction. J. Pharmacol. Methods 1986, 15, 255-261.