2-(4,5-Dihydro-1H-imidazol-2-yl)indazole (indazim) derivatives as selective I2 imidazoline receptor ligands

European Journal of Pharmaceutical Sciences

Volumn 20, Issue 2, 2003, Pages 201-208

  Saczewski, F ^a   Hudson, A L ^b   Tyacke, R J ^b   Nutt, D J ^b   Man, J ^b   Tabin, P ^a   Saczewski, J ^a  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

2 (4,5 Dihydro 1H imidazol 2 yl)indazoles; Selective imidazoline I2 receptor ligands; Structure; Synthesis

Indexed keywords

ALKYLATION; BINDING ENERGY; DERIVATIVES; ORGANIC COMPOUNDS;

LIGANDS;

DRUG PRODUCTS;

2 (4,5 DIHYDRO 1H IMIDAZOL 2 YL) 4 METHYL 1H INDAZOLE; 2 (4,5 DIHYDRO 1H IMIDAZOL 2 YL) 4,5,6,7 TETRAHYDRO 1H INDAZOLE; 2 (4,5 DIHYDRO 1H IMIDAZOL 2 YL) 5 METHYL 1H INDAZOLE; 2 (4,5 DIHYDRO 1H IMIDAZOL 2 YL) 6 METHYL 1H INDAZOLE; 2 (4,5 DIHYDRO 1H IMIDAZOL 2 YL) 7 METHOXY 1H INDAZOLE; 2 (4,5 DIHYDRO 1H IMIDAZOL 2 YL) 7 METHYL 1H INDAZOLE; 4 CHLORO 2 (4,5 DIHYDRO 1H IMIDAZOL 2 YL) 1H INDAZOLE; 5 CHLORO 2 (4,5 DIHYDRO 1H IMIDAZOL 2 YL) 1H INDAZOLE; 7 CHLORO 2 (4,5 DIHYDRO 1H IMIDAZOL 2 YL) 1H INDAZOLE; ALPHA 2 ADRENERGIC RECEPTOR; IMIDAZOLINE I2 RECEPTOR; INDAZIM; INDAZOLE DERIVATIVE; RADIOLIGAND; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL TISSUE; BINDING AFFINITY; BINDING ASSAY; BRAIN; CONFERENCE PAPER; DRUG BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; STEREOCHEMISTRY;

EID: 0141782718     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0928-0987(03)00182-9     Document Type: Conference Paper

References (32)

1. Ainsworth C. Indazole. Org. Synth. Coll. 4:1963;536-539.
2. 2 ligands: a significant model through a combined exploration of structural diversity and methodology. J. Med. Chem. 43:2000;1109-1122.
3. 2-imidazoline receptor ligand LSL 60101. Br. J. Pharmacol. 130:2000;1767-1776.
4. Carrieri A., Brasili L., Leonetti F., Pigini M., Giannella M., Bousquet P., Carotti A. 2-D and 3-D modeling of imidazoline receptor ligands: insight into pharmacophore. Bioorg. Med. Chem. 5:1997;843-856.
5. 50) of an enzymatic reaction. Biochem. Pharmacol. 22:1973;3099-3108.
6. Diamant S., Eldar-Geva T., Atlas D. Imidazoline binding sites in human placenta. Evidence for the heterogenicity and a search for physiological function. Br. J. Pharmacol. 106:1992;101-108.
7. Eglen R.M., Hudson A.L., Kendall D.A., Nutt D.J., Morgan N.G., Wilson V.G., Dillon M.P. 'Seeing through a glass darkly': casting light on imidazoline 'I' sites. Trends Pharmacol. Sci. 19:1998;381-390.
8. Garcia-Sevilla J.A., Escriba P.V., Sastre M., Walzer C., Busquets X., Jaquet G., Reis D.J., Guiman J. Immunodetection and quantitation of imidazoline receptor proteins in platelets of patients with major depression and in brains of suicide victims. Arch. Gen. Psychiatry. 53:1996;803-810.
9. 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. 247:1998;95-98.
10. 2 binding sites in the frog brain. Br. J. Pharmacol. 119:1996;39.
11. Hudson A.L., Gough R., Tyacke R., Lione L., Lalies M., Lewis J., Husbands S., Knight P., Murray F., Hutson P., Nutt D.J. Novel selective compounds for the investigation of imidazoline receptors. Ann. NY Acad. Sci. 881:1999;81-91.
12. Hudson A.L., Nutt D.J., Husbands S.M. Imidazoline receptors and their role in depression. Pharm. News. 8:2001;26-32.
13. Jackson H.C., Nutt D.J. Imidazoline receptor and ingestion. Cooper S.J., Clifton P.G. Drug Receptor Subtypes and Ingestive Behaviour. 1996;267-283 Academic Press, London.
14. 2 receptors. Eur. J. Pharmacol. 353:1998;123-135.
15. 2 imidazoline receptors. Br. J. Pharmacol. 116:1995;1729-1736.
16. 3H]idazoxan binding sites in the frontal cortex of depressed suicide victims. Biol. Psychiatry. 34:1993;498-501.
17. 2-imidazoline drugs in rats. Br. J. Pharmacol. 111:1994;298P.
18. Molderings G.J. Imidazoline receptors: basic knowledge, recent advances and future prospects for therapy and diagnosis. Drugs Future. 22:1997;757-772.
19. 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. NY Acad. Sci. 763:1995;125-140.
20. 1H nuclear magnetic resonance spectra of indazoles and benzotriazoles. J. Chem. Soc. Perkin Trans. II:1975;1695-1700.
21. Pigini M., Bousquet P., Carotti A., Dontenvill 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. 5:1997;833-841.
22. Pigini M., Bousquet P., Brasili L., Carrieri A., Cavagna R., Dontenvill M., Gentili F., Giannella M., Leonetti F., Piergentili A., Quaglia W., Carotti A. Binding of tracizoline to the imidazoline receptor: the role of lipophylicity in quantitative structure-activity relationship models. Bioorg. Med. Chem. 6:1998;2245-2260.
23. 2 binding sites. Eur. J. Pharmacol. 392:2000;41-49.
24. Reynolds G.P., Boulton R.M., Pearson S.J., Hudson A.L., Nutt D.J. Imidazoline binding sites in Huntington's and Parkinson's disease pattern. Eur. J. Pharmacol. 301:1996;R19-R21.
25. 2 binding site ligand, in rat brain. Eur. J. Pharmacol. 450:2002;55-60.
26. Rüchardt, C., Hassmann, V., 1980. Aromatische diazoniumsalze, X. Durchfuhrung der Jacobsonschen indazolsyntheze im eintopfrerfahren. Liebigs Ann. Chem. 908-927.
27. 2 imidazoline sites) are increased in postmorten brain from patients with Alzheimer's disease. Neurosci. Lett. 160, 109-112.
28. Saczewski F., Saczewski J., Gdaniec M. Carbon disulfide promoted reactions of 2-chloro-4,5-dihydroimidazole with N-nucleophiles. Chem. Pharm. Bull. 49:2001;1203-1206.
29. 2 imidazoline receptors in the postmortem brains of heroin addicts. NeuroReport. 7:1996;509-512.
30. Tesson F., Limon J., Parini A. Tissue-specific localization of mitochondrial imidazoline-guanidinium receptive sites. Eur. J. Pharmacol. 219:1992;225-238.
31. Timmermans P.B.M.W.M., van Zweiten P.A. Quantitative structure-activity relationships in centrally acting imidazolines structurally related to clonidine. J. Med. Chem. 20:1977;1636-1644.
32. Trani A., Belasio E. Synthesis of 2-chloroimidazoline and its reactivity with aromatic amines, phenols and thiophenols. J. Heterocycl. Chem. 11:1974;257-261.