3D-QSAR CoMFA study on imidazolinergic I2 ligands: A significant model through a combined exploration of structural diversity and methodology

Journal of Medicinal Chemistry

Volumn 43, Issue 6, 2000, Pages 1109-1122

  Baurin, Nicolas ^a   Vangrevelinghe, Eric ^a   Morin Allory, Luc ^a   Mérour, Jean Yves ^a   Renard, Pierre ^b   Payard, Marc ^c   Guillaumet, Gérald ^a   Marot, Christophe ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b ADIR   (France)

^c UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLINE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; ASTROCYTE; BINDING AFFINITY; LIGAND BINDING; METHODOLOGY; MOLECULAR RECOGNITION; NEUROTRANSMITTER RELEASE; PHARMACOPHORE; PREDICTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

DRUG DESIGN; IMIDAZOLES; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RECEPTORS, DRUG; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034704736     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991124t     Document Type: Article

References (40)

1. Bousquet, P.; Feldman, J.; Schwartz, J. Central cardiovascular effects of alpha adrenergics drugs: differences between catecholamines and imidazolines. J. Pharmacol. Exp. Ther. 1984, 230, 232-236.
2. Molderings, G. J. Imidazoline receptors: basic knowledge, recent advances and future prospects for therapy and diagnosis. Drugs Future 1997, 22, 757-772.
3. Chan, S. L. F. Clonidine-displacing substance and its putative role in control of insulinsecretion: A minireview. Gen. Pharmacol. 1998, 31, 525-529.
4. Reis, D. J.; Regunathan, S. Agmatine: an endogenous ligand at imidazoline receptors may be a novel neurotransmitter in brain. J. Auton. Nerv. Syst. 1998, 72, 80-85.
5. 1-imidazoline agonist moxonidine decreases sympathetic nerve activity and blood pressure in hypertensives. Hypertension 1998, 32, 1022-1027.
6. Molderings, G. J.; Gothert, M. Imidazoline binding sites and receptors in cardiovascular tissue. Gen. Pharmacol. 1999, 32, 17-22.
7. Chu, T. C.; Socci, R. R.; Ogidigben, M. J.; Potter, E. D. Potential mechanisms of moxonidine-induced ocular hypotension: role of norepinephrine. J. Ocul. Pharmacol. Ther. 1997, 13, 489-496.
8. 2-type imidazoline receptors: an in vivo and in vitro electrophysiological study. Br. J. Pharmacol. 1998, 125, 1685-1694.
9. Ernsberger, P.; Ishizuka, T.; Liu, S.; Farrell, C. J.; Bedol, D.; Koletsky, R. J.; Friedman, J. E. Mechanisms of antihyperglycemic effects of moxonidine in the obese spontaneously hypertensive Koletsky rat (SHROB). J. Pharmacol. Exp. Ther. 1999, 288, 139-147.
10. Rondu, F.; Le Bihan, G.; Wang, X.; Lamouri, A.; Touboul, E.; Dive, G.; Bellahsene, T.; Pfeiffer, B.; Renard, P.; Guardiola-Lemaitre, B.; Manechez, D.; Penicaud, L.; Ktorza, A.; Godfroid, J. J. Design and Synthesis of Imidazoline Derivatives Active on Glucose Homeostasis in a Rat Model of Type II Diabetes. 1. Synthesis and Biological Activities of N-Benzyl-N′-(arylalkyl)-2-(4′,5′-dihydro-1′H-imidazol- 2′-y1)piperazines. J. Med. Chem. 1997, 40, 3793-3803.
11. Garcia-Sevilla, J. A.; Escriba, P. V.; Walzer, C.; Bouras, C.; Guimon, J. Imidazoline receptor proteins in brains of patients with Alzheimer's disease. Neurosci. Lett. 1998, 247, 95-98.
12. Heemskerk, F. M. J.; Dontenwill, M.; Greney, H.; Vonthron, C.; Bousquet, P. Evidence for the existence of imidazoline-specific binding sites in synaptosomal plasma membranes of the bovine brainstem. J. Neurochem. 1998, 71, 2193-2202.
13. Remaury, A.; Missy, K.; Parini, A. Characterization of [H-3]-idazoxan binding proteins in solubilized membranes from rabbit and human liver. J. Auton. Nerv. Syst. 1998, 72, 111-117.
14. Nutt, D. J.; French, N.; Handley, S.; Hudson, A.; Husbands, S.; Jackson, H.; Jordan, S.; Lalies, M. D.; Lewis, J.; Lione, L.; Mallard, N.; Pratt, J. Functional studies of specific imidazoline-2 receptor ligands. Ann. N. Y. Acad. Sci. 1995, 763, 125-139.
15. Molderings, G. J.; Donecker, K.; Burian, M.; Simon, W. A.; Schroder, D. W.; Gothert, M. Characterization of 1-2 imidazoline and a binding sites in the rat and human stomach. J. Pharmacol. Exp. Ther. 1998, 285, 170-177.
16. Ivanov, T. R.; Feng, Y.; Wang, H.; Regunathan, S.; Reis, D. J.; Chikkala, D. N.; Gupta, P.; Jones, J. C.; Piletz, J. E. Imidazoline receptor proteins are regulated in platelet-precursor MEG-01 cells by agonists and antagonists. J. Psychiatr. Res. 1998, 32, 65-79.
17. Boronat, M. A.; Olmos, G.; Garcia-Sevilla, J. A. Attenuation of tolerance to opioid-induced antinociception and protection against morphine-induced decrease of neurofilament proteins by idazoxan and other I-2-imidazoline ligands. Br. J. Pharmacol. 1998, 125, 175-185.
18. Smyth, D. D.; Penner, S. B. Imidazoline receptor mediated natriuresis: central and/or peripheral effect. J. Auton. Nerv. Syst. 1998, 72, 155-162.
19. Gargalidis-Moudanos, C.; Pizzinat, N.; Javoy-Agid, F.; Remaury, A.; Parini, A. I2 Imidazoline binding sites and monoamine oxidase activity in human postmortem brain from patients with Parkinson's disease. Neurochem. Int. 1997, 30, 31-36.
20. Michel, M. C.; Ernsberger, P. Keeping an eye on the I site: imidazoline-preferring receptors. Trends Pharmacol. Sci. 1992, 13, 369-370.
21. Tesson, F.; Prib-Buus, C.; Lenoine, A.; Pegorier, J. P.; Parini, A. Subcellular distribution of imidazoline-guanidinium-receptive sites in human and rabbit liver. Major localization to the mitochondrial outer membrane. J. Biol. Chem. 1991, 266, 155-160.
22. Cramer, R. D., III; Patterson, D. E.; Bunce, J. D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
23. 2 imidazoline receptor: The role of lipophilicity in quantitative structure-activity relationship models. Bioorg. Med. Chem. 1998, 6, 2245-2260.
24. Carrieri, A.; Brasili, L.; Leonetti, F.; Pigini, M.; Giannella, M.; Bousquet, P.; Carotti, A. 2-D and 3-D modeling of imidazoline receptor ligands: insights into pharmacophore. Bioorg. Med. Chem. 1997, 5, 843-856.
25. 1A Receptor Ligands and Potential Anxiolytic Agents. 2. Synthesis and Quantitative Structure-Activity Relationship Studies of Spiro[pyrrolidine- and piperidine-2,3′(2′H)-benzopyrans]. J. Med. Chem. 1996, 39, 4285-4298.
26. Marot, C.; Chavatte, P.; Morin-Allory, L.; Viaud, M. C.; Guillaumet, G.; Renard, P.; Lesieur, D.; Michel, A. Pharmacophoric Search and 3D-QSAR Comparative Molecular Field Analysis Studies on Agonists of Melatonin Sheep Receptors. J. Med. Chem. 1998, 41, 4453-4465.
27. Pigini, M.; Bousquet, P.; Carotti, A.; Dontenwill, M.; Giannella, M.; Moriconi, R.; Piergentili, A.; Quaglia, W.; Tayebati, S. K.; Brasili, L. Imidazoline receptors: qualitative structure-activity relationships and discovery of tracizoline and benazoline. Two Ligands with high affinity and unprecedented selectivity. Bioorg. Med. Chem. 1997, 5, 833-841.
28. Compounds from our laboratories; synthesis and structural data to be published elsewhere.
29. Oxford Molecular Ltd., The Medawar Centre, Oxford Science Park, Sandford-on-Thames, Oxford OX4 4GA, U.K.
30. Sybyl 6.5, Tripos Associates Inc., 1699 South Hanley Rd., St. Louis, MO 63144.
31. Stewart, J. P. P. MOPAC: a semiempirical molecular orbital program. J. Comput.-Aided Mol. Des. 1990, 4, 1-103.
32. (a) Gaillard, P.; Carrupt, P. A.; Testa, B.; Boudon, A. Molecular lipophilicity potential, a toll in 3D-QSAR. Method and Applications. J. Comput.-Aided Mol. Des. 1994, 8, 83-96.
33. (b) Institut of Medicinal Chemistry, University of Lausanne, BEP CH-1015 Lausanne, Switzerland.
34. Audry, E.; Dubost, J. P.; Dallet, P.; Langlois, M. H.; Colleter, J. C. The Molecular Lipophilic Potential: Application to a series of beta-adrenolytic amines. Eur. J. Med. Chem. 1989, 24, 155-161.
35. Carbo, R.; Domingo, L. LCAO-MO Similarity Measures and Taxonomy. Int. J. Quantum Chem. 1987, 32, 517-545.
36. Viswanadhan, V. N.; Ghose, A. K.; Revankar, G. R.; Robins, R. K. Atomic physicochemical parameters for three-dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics. J. Chem. Inf. Comput. Sci. 1989, 29, 163-172.
37. Good, A. C.; Richards, W. G. Rapid Evaluation of Shape Similarity Using Gaussian Functions. J. Chem. Inf. Comput. Sci. 1993, 33, 112-116.
38. Neider, J. A.; Mead, R. A simplex method for function minimization. Comput. J. 1965, 7, 308-313.
39. Vinter, J. G.; Davis, A.; Saunders, M. R. Strategic approaches to drug design. 1. An integrated software framework for molecular modeling. J. Comput.-Aided Mol. Des. 1987, 1, 31-51.
40. Van de Waterbeemd, H.; Testa, B. The parametrization of lipophilicity and other structural properties in drug design. In Advances in Drug Research; Testa, B., Ed.; Academic Press: London, 1987; Vol. 16, pp 87-227.