2-(2-phenylcyclopropyl)imidazolines: Reversed enantioselective interaction at I1 and I2 imidazoline receptors [1]

Journal of Medicinal Chemistry

Volumn 42, Issue 15, 1999, Pages 2737-2740

  Quaglia, Wilma ^a   Bousquet, Pascal ^b   Pigini, Maria ^a   Carotti, Angelo ^c   Carrieri, Antonio ^c   Dontenwill, Monique ^b   Gentili, Francesco ^a   Giannella, Mario ^a   Maranca, Francoise ^b   Piergentili, Alessandro ^a   Brasili, Livio ^d  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c UNIVERSITY OF BARI   (Italy)

^d UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA 1 ADRENERGIC RECEPTOR STIMULATING AGENT; CIRAZOLINE; IMIDAZOLINE DERIVATIVE; IMIDAZOLINE I1 RECEPTOR; IMIDAZOLINE I2 RECEPTOR; TRACIZOLINE; UNCLASSIFIED DRUG;

ANIMAL CELL; BINDING COMPETITION; CIS TRANS ISOMERISM; DRUG PURITY; DRUG RECEPTOR BINDING; ENANTIOMER; GEOMETRY; LETTER; MOLECULAR INTERACTION; NONHUMAN; RABBIT; RAT; STEREOISOMERISM;

ANIMALS; CEREBRAL CORTEX; IMIDAZOLES; KIDNEY; LIGANDS; MODELS, MOLECULAR; PC12 CELLS; RABBITS; RADIOLIGAND ASSAY; RATS; RECEPTORS, DRUG; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033615047     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991049m     Document Type: Letter

References (23)

1. Reis, D. J., Bousquet, P., Parini, A., Eds. The Imidazoline Receptor: Pharmacology, Functions, Ligands, and Relevance to Biology and Medicine. Ann. N. Y. Acad. Sci. 1995, 763.
2. Regunathan, S.; Reis, D. J. Imidazoline Receptors and their Endogenous Ligands. Annu. Rev. Pharmacol. Toxicol. 1996, 36, 511-544.
3. Molderings, G. J. Imidazoline Receptors: Basic Knowledge, Recent Advances and Future Prospects for Therapy and Diagnosis. Drugs Future 1997, 22, 757-772.
4. Milligan, C. M.; MacKinnon, A. C. Imidazoline Receptor Ligands. Drugs New Perspect. 1997, 10, 74-84.
5. Bousquet, P. Imidazoline Receptors. Neurochem. Intern. 1997, 30, 3-7.
6. Brasili, L.; Pigini, M.; Marucci, G.; Quaglia, W.; Malmusi, L.; Lanier, M. L.; Lanier, B. Separation of α-Adrenergic and Imidazoline/Guanidinium Receptive Sites (IGRS) Activity in a Series of Imidazoline Analogues of Cirazoline. Bioorg. Med. Chem. 1995, 3, 1503-1509.
7. Brasili, L.; Pigini, M.; Bousquet, P.; Carotti, A.; Dontenwill, M.; Giannella, M.; Moriconi, R.; Piergentili, A.; Quaglia, W.; Tayebati, S. K. Discovery of Highly Selective Imidazoline Receptor Ligands. In Perspective in Receptor Research; Giardinà, D., Piergentili, A., Pigini, M., Eds.; Elsevier: Amsterdam, 1996; pp 361-373.
8. 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.
9. 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.
10. 2 Imidazoline Receptor: The Role of Lipophilicity in Quantitative Structure-Activity Relationship Models. Bioorg. Med. Chem. 1998, 6, 2245-2260.
11. Kaiser, C.; Lester, B. M.; Zirkle, C. L.; Burger, A.; Davis, C. S.; Delia, T. J.; Zirngibl, L. 2-Substituted Cyclopropylamines. I. Derivatives and Analogues of 2-Phenylcyclopropylamine. J. Med. Chem. 1962, 5, 1243-1265.
12. 4) C, H, N.
13. Kaiser, C.; Weinstock, J.; Olmstead, M. P. cis-2-Phenylcyclopropanecarboxylic acid (cyclopropanecarboxylic acid, 2-phenyl-, cis). Org. Synth. 1988, VI, 913-915 and references therein.
14. 4) C, H, N.
15. Riley, T. N.; Brier, C. G. Absolute Configuration of (+)-and (-)-trans-2-Phenylcyclopropylamine Hydrochloride. J. Med. Chem. 1972, 15, 1187-1188.
16. Inouye, Y.; Sugita, T.; Walborsky, H. M. Cyclopropanes. XVII. The Absolute Configurations of trans-1,2-Cyclopropanedicarboxylic Acid and trans-2-Phenylcyclopropanecarboxylic Acid. Tetrahedron 1964, 20, 1695-1699.
17. 2N); 4.65 (1H, m, COOCH); 7.09-7.31 (5H, m, Ar-H).
18. 1-Imidazoline receptors to diacylglyceride accumulation in PC12 rat pheochromocytoma cells. Mol. Pharmacol. 1996, 49, 668-675.
19. -4 M). Incubations were performed for 30 min at 25 °C. Nonspecific binding was determined with 10 μM BDF 6143.
20. 50) of an Enzimatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
21. 1-Imidazoline Sites in Bovine Adrenal Medullary Membranes. Naunyn-Scmiedeberg's Arch. Pharmacol. 1993, 348, 70-76.
22. 1-Imidazoline Binding Sites and the High Affinity State of Alpha-2 Adrenoceptor Subtypes. J. Pharmacol. Exp. Ther. 1996, 279, 694-702.
23. In the conformations selected for CoMFA studies, however, the angle values were 29.5°, 114°, and 132° for 3, (1S,2S)-(+)-4b, and (1R,2R)-(-)-4b, which imply energy differences of 0.50, 1.09, and 0.60 kcal/mol, respectively.