2-(4,5-Dihydroimidazol-2-yl)benzimidazoles as highly selective imidazoline I2/adrenergic α2 receptor ligands

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 19, 2006, Pages 6679-6685

  Saczewski, Francieszek ^a   Tabin, Piotr ^a   Tyacke, Robin J ^b   Maconie, Alys ^b   Saczewski, Jarosław ^a   Kornicka, Anita ^a   Nutt, David J ^b   Hudson, Alan L ^c  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

^c UNIVERSITY OF ALBERTA   (Canada)

Author keywords

2 (4,5 Dihydroimidazol 2 yl)benzimidazoles; Radioligand binding studies; Selective imidazoline I2 receptor ligands; Synthesis

Indexed keywords

2 (4,5 DIHYDRO 1H IMIDAZOL 2 YL) 4 METHYL 1H BENZIMIDAZOLE; 4 CHLORO 2 (4,5 DIHYDRO 1H IMIDAZOL 2YL) 1H BENZIMIDAZOLE; ALPHA 2A ADRENERGIC RECEPTOR; IMIDAZOLE DERIVATIVE; IMIDAZOLINE I2 RECEPTOR; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; LIGAND BINDING;

ANIMALS; BENZIMIDAZOLES; ELECTRONS; INDICATORS AND REAGENTS; LIGANDS; MALE; RADIOLIGAND ASSAY; RATS; RATS, WISTAR; RECEPTORS, ADRENERGIC, ALPHA-2; RECEPTORS, DRUG; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33747191232     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.05.062     Document Type: Article

References (23)

1. Hudson A.L., Nutt D.J., and Husbands S.M. Pharm. News 8 (2002) 18
2. Edwards M.M., et al. Br. J. Pharmacol. 135 (2002) 110P
3. Meana J.J., Barturen F., Martin I., and Garcia-Sevilla J.A. Biol. Psychiatry 34 (1993) 498
4. Garcia-Sevilla J.A., Escriba P.V., Sastre M., Walzer C., Busquets X., Jaquet G., Reis D.J., and Guiman J. Arch. Gen. Psychiatry 53 (1996) 803
5. Garcia-Sevilla J.A., Escriba P.V., Walzer C., Bouras C., and Guimon J. Neurosci. Lett 247 (1998) 95
6. Sastre M., Ventayol P., and Garcia-Sevilla J.A. NeuroReport 7 (1996) 509
7. Hudson A.L., Nutt D.J., and Husbands S.M. Pharm. News 8 (2001) 26-32
8. Reynolds G.P., Boulton R.M., Pearson S.J., Hudson A.L., and Nutt D.J. Eur. J. Pharmacol. 301 (1996) R19
9. Ruiz J., Martin I., Callado I.F., Meana J.J., Barturen F., and Garcia-Sevilla J.A. Neurosci. Lett. 160 (1993) 109
10. Nutt D.J., French N., Handley S., Hudson A.L., Husbands S., Jackson H., Jordan S., Lalies M.D., Lewis J., Lione L., Mallard N., and Prattm J. Ann. NY Acad. Sci. 763 (1995) 125
11. Hudson A.L., Gough R., Tyacke R.J., Liona L., Lalies M., Lewis J., Husbands S., Knight P., Murray F., Hutson P., and Nutt D.J. Ann. NY Acad. Sci. 881 (1999) 81
12. Pigini M., Bousquet P., Carotti A., Dontenwill M., Giannella M., Mariconi R., Piergentilli A., Quaglia W., Tayebati S.K., and Brasili L. Bioorg. Med. Chem. 5 (1997) 833
13. Sa{ogonek}czewski F., Hudson A.L., Tyacke R.J., Nutt D.J., Man J., Tabin P., and Sa{ogonek}czewski J. Eur. J. Pharm. Sci. 20 (2003) 201
14. Pigini M., Bousquet P., Brasili L., Carrieri A., Cavagna R., Dontenwill M., Gentilli F., Giannella M., Leonetti F., Piergentilli A., Quaglia W., and Carotti A. Bioorg. Med. Chem. 6 (1998) 2254
15. Anastassiadou M., Daunon S., Crane L., Bazirad-Mouysset G., Payard M., Caignard D.-H., Rettori M.-C., and Renard P. Bioorg. Med. Chem. 9 (2001) 585
16. Chang-Fong J., Tyacke R.J., Lau A., Westaway J., Hudson A.L., and Glennon R.A. Bioorg. Med. Chem. Lett. 14 (2004) 1003
17. Glennon R.A., Grella B., Tyacke R.J., Lau A., Westaway J., and Hudson A.L. Bioorg. Med. Chem. Lett. 14 (2004) 999
18. Glennon R.A., Grella B., Tyacke R.J., Lau A., Westaway J., and Hudson A.L. Bioorg. Med. Chem. Lett. 14 (2004) 527
19. Ennis B.C., Holan G., and Samuel E.L. J. Chem. Soc. C (1967) 33
20. Möller, H.; Gloxhuber, Ch.; Patent DE 2436279, 1976.
21. Cheng Y.C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
22. a values were determined at 25 °C by potentiometric titration using Metrohm 794 Titrino apparatus with the TiNet 2.5 software.
23. The geometry of the compounds 4, 13 and I was fully optimized using a molecular orbital ab initio method at the Hartree-Fock level of theory with the 6-31G** basis set. The calculations were carried out using the PCSpartan program distributed by Wavefunction Inc. and installed on a PC Pentium IV computer.