Synthesis and preliminary pharmacological evaluation of some cytisine derivatives

Farmaco

Volumn 54, Issue 7, 1999, Pages 438-451

  Canu Boido, Caterina ^a   Sparatore, Fabio ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

Cardiovascular agents; Cytisine derivatives; Nicotine receptors; Quinolizidine derivatives

Indexed keywords

ALPHA 1 ADRENERGIC RECEPTOR; ALPHA 2 ADRENERGIC RECEPTOR; ANTIDIABETIC AGENT; BETA ADRENERGIC RECEPTOR; CYTISINE; DOPAMINE; NICOTINIC RECEPTOR; THROMBOCYTE ACTIVATING FACTOR;

ANALGESIA; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIHYPERTENSIVE ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BLOOD BRAIN BARRIER; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HEART PROTECTION; MALE; MORTALITY; NONHUMAN; ORAL DRUG ADMINISTRATION; RAT; THROMBOCYTE AGGREGATION INHIBITION; ULCER HEALING;

ADRENERGIC ALPHA-ANTAGONISTS; ALKALOIDS; ALKYLATION; ANIMALS; ANTI-ARRHYTHMIA AGENTS; AZOCINES; BINDING, COMPETITIVE; CHOLINERGIC AGENTS; GUINEA PIGS; HYPOGLYCEMIC AGENTS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; NICOTINIC AGONISTS; NICOTINIC ANTAGONISTS; QUINOLIZINES; RATS; RATS, WISTAR; RECEPTOR, CHOLECYSTOKININ A; RECEPTORS, ADRENERGIC, ALPHA-2; RECEPTORS, CHOLECYSTOKININ; RECEPTORS, NICOTINIC; RECEPTORS, VASOACTIVE INTESTINAL PEPTIDE; SPECTROPHOTOMETRY, INFRARED;

EID: 0033618538     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(99)00049-X     Document Type: Article

References (44)

1. Bovet D., Bovet Nitti F. Structure et Activité Pharmaco-dynamique des Médicaments du Système Nerveux Végétatif. 1948;605-606 Karger, Basel.
2. Barlow R.B., Mc Leod L.J. Some studies on cytisine and its methylated derivatives. Br. J. Pharmacol. 35:1969;161-174.
3. P. Lebeau, M.M. Janot, Traité de Pharmacie Chimique, tome IV, Masson, Paris, 1955, p. 2859.
4. Dallemagne M.J., Heymans C.H. Respiratory stimulants. Manske R.H.F. The Alkaloids. 5:1955;109-139 Academic Press, New York.
5. Zakusov V.V. Farmacologiia. 1960;203 Medgiz, Moscow.
6. I. Murakoshi, Y. Fuji, S. Takedo, J. Arai, Lupine alkaloids as antidiabetics, Jpn. Kokai Tokkyo Koho, Japanese Patent 04-295480 (20-10-1992); Chem. Abstr. 118 (1993) 45733.
7. I. Murakoshi, Y. Fujii, H. Kawamura, H. Marayama, Lupine alkaloids as antiinflammatory agents, Jpn. Kokai Tokkyo Koho, JP 04-295479 (20-10-1992); Chem. Abstr. 118 (1993) 45734.
8. Waunacott S. Brain nicotine binding sites. Hum. Toxicol. 6:1987;343-353.
9. 3H]Cytisine binding to nicotine cholinergic receptors in brain. Mol. Pharmacol. 39:1991;9-12.
10. McDonald I.A., Cosford N., Vernier J.M. Nicotinic acetylcholine receptors: molecular biology, chemistry and pharmacology. Ann. Rep. Med. Chem. 30:1995;41-50.
11. Gatti G.L., Robustelli F., Bucci L. L'azione facilitante della nicotina sull'apprendimento di comportamenti condizionati negli animali di laboratorio e possibili deduzioni applicabili alla clinica. Clin. Terap. 34:1965;388-398.
12. Perry E.K., Morris C.M., Court J.A., Cheng A., Fairbain A.F., Mc Keith I.G., Irving D., Brown A., Perry R.H. Alteration in nicotine binding sites in Parkinson's disease. Lewy body dementia and Alzheimer's disease: possible index of early neuropathology. Neuroscience. 64:1995;385-395.
13. Decker M.W., Majchrzak M.J., Arneric S.P. Effects of lobeline, a nicotinic receptor agonist, on learning and memory. Pharmacol. Biochem. Behav. 45:1993;571-576.
14. Hamann S.R., Martin W.R. Hyperalgesic and analgesic actions of morphine, U50-488, naltrexone and (-)-lobeline in the rat brainstem. Pharmacol. Biochem. Behav. 47:1994;197-201.
15. Williams M., Sullivan J.P., Arneric S.P. Neuronal nicotinic acetylcholine receptors. Drug News Perspect. 7:1994;205-223.
16. Luputiu G., Gilau L. N-Aryl-thiocarbamylcytisine Derivate. Arch. Pharm. 302:1969;943-945.
17. A.E. Vezen, K.K. Khaidarov, Y.D. Sadykov, Pharmacology of para-nitrobenzoylcytisine, Dokl. Akad., Nauk Tadsh. SSR 25 (1982) 351-352; Chem. Abstr. 98 (1983) 137457.
18. A.E. Vezen, K.K. Khaidarov, Y.D. Sadykov, Pharmacology of para-nitrobenzoylcytisine, Dokl. Akad., Nauk Tadsh. SSR 25 (1982) 351-352; Chem. Abstr. 98 (1983) 137457.
19. H.R. Ing, R.P. Patel, Synthesis of local anesthetics from cytisine, J. Chem. Soc. (1936) 1774-1775.
20. Sheridan R.P., Nilakontan R., Dixon J.S., Venkataraghavan R. The ensemble approach to distance geometry: application to the nicotinic pharmacophore. J. Med. Chem. 29:1986;899-906.
21. Barlow R.B., Johnson O. Relations between structure and nicotine like activity: X-ray crystal structure analysis of (-)-cytisine and (-)-lobeline hydrochloride and a comparison with (-)-nicotine and other nicotine-like compounds. Br. J. Pharmacol. 98:1989;799-808.
22. Murakoshi I., Fukuchi K., Haginiwa J., Ohmiya S., Otomasu H. N-(3-Oxobutyl)cytisine: a new lupin alkaloid from Echinosophora koreensis. Phytochemistry. 16:1977;1460-1461.
23. V. Boido, M. Ercoli, F. Sparatore, Synthesis of 2-aryl-2-dehydro and 2-arylsparteines of pharmacological interest, XVII Congresso Nazionale Soc. Chim. Ital. Januachem 92, Genoa, 25-30 October, 1992, Atti I, 100-101.
24. 2 receptors. J. Med. Chem. 36:1993;1488-1495.
25. Rutenber E., Fauman E.B., Keenan R.J., Fong S., Furth P.S., Ortiz de Montellano P.R., Meng E., Kuntz J.D., De Camp D.L., Salto R., Rosé J.L., Craik C.S., Stroud R.M. Structure of a non-peptide inhibitor complexed with HIV-1 protease. J. Biol. Chem. 268:1993;15343-15346.
26. De Voss J.J., Sui Z., De Camp D.L., Salto R., Babè L.M., Craik C.S., Ortiz de Montellano R.R. Haloperidol-based irreversible inhibitors of HIV-1 and HIV-2 proteases. J. Med. Chem. 37:1994;665-673.
27. Villarroya M., Gaudia L., Lopez M.G., Garcia A.G., Cueto S., Garcia-Navio J.L., Alvarez-Builla J. Synthesis and pharmacology of alkandiguanidinium compounds that block the neuronal nicotinic acetylcholine receptor. Bioorg. Med. Chem. 4:1996;1177-1183.
28. Z.P. Pakudina, S.Y. Yunusov, Derivatives of cytisine, Izvest. Akad. Nauk Uzbek. SSR Ser. Khim. Nauk. (1957) 69-75; Chem. Abstr. 54 (1960) 6783.
29. Z.P. Pakudina, S.Y. Yunusov, Derivatives of cytisine, Izvest. Akad. Nauk Uzbek. SSR Ser. Khim. Nauk. (1957) 69-75; Chem. Abstr. 54 (1960) 6783.
30. Lopez-Rodriguez M.L., Morcillo M.J., Fernandez E., Porras E., Murcia M., Sanz A.M., Oreusanz L. Synthesis and structure-activity relationship of a new model of arylpiperazine. 3. 2-[ω-(4-Arylpiperazin-1-yl)alkyl]-perhydropyrrolo[1,2-c]imidazoles and -perhydro-imidazo[1,5-a]pyridines: study of the influence of the terminal amide fragment on 5-HT1A affinity/selectivity. J. Med. Chem. 40:1997;2653-2656.
31. Ruenitz P.C., Mokler C.M. Analogues of sparteine. Antiarrythmic activity of selected N,N-disubstituted bispidines. J. Med. Chem. 20:1997;1668-1671.
32. Ohmiya S., Otomasu H., Haginawa J., Murakoshi I. (-)-12-Cytisineacetic acid, a new alkaloid in Euchresta japonica. Phytochemistry. 18:1979;649-650.
33. Novelli F., Sparatore F. Synthesis and preliminary pharmacological evaluation of 3-[2-(1-arylpiperazin-4-yl)ethyl]-3,4-dihydro-3-methyl-6-R-1,2,4-benzotriazines. Farmaco. 51:1996;551-558.
34. Boido Canu C., Boido V., Sparatore F., Sparatore A. Sintesi ed attività farmacologica di 3-chinolizidin-1′-il-5-R-indoli. Farmaco Ed. Sci. 43:1988;801-817.
35. Novelli F., Sparatore F. Thiolupinine and some derivatives of pharmacological interest. Farmaco. 48:1993;1021-1049.
36. Sparatore A., Sparatore F. Preparation and pharmacological activities of 10-homolupinanoyl-2-R-phenothiazines. Farmaco. 49:1994;5-17.
37. Sparatore A., Sparatore F. Preparation and pharmacological activities of homolupinanoyl anilides. Farmaco. 50:1995;153-166.
38. Iusco G., Boido V., Sparatore F. Synthesis and preliminary pharmacological investigation of N-lupinyl-2-methoxybenzamides. Farmaco. 51:1996;159-174.
39. Novelli F., Sparatore F. Preparation and pharmacological activities of spiro[3,4-dihydro-6,7-R-1,2,4-benzotriazine-3,4′-(1′-substituted) piperidines]. Farmaco. 51:1996;541-550.
40. 2-Adrenergic agonist and antagonist activity of the respective (-)- and (+)-enantiomers of 6-ethyl-9-oxaergoline (EOE). Eur. J. Pharmacol. 85:1982;211-215.
41. Moore P.K., Griffiths R.J. Pre-synaptic and post-synaptic effects of xylazine and naphazoline on the bisected rat vas deferens. Arch. Int. Pharmacodyn. 260:1982;70-77.
42. Chang R.S.L., Lotti V.J., Chen T.B., Kunkel K.A. Characterization of the binding of tritiated racemic L-364718, a new potent non-peptide cholecystokinin antagonist radioligand for peripheral receptors. Mol. Pharmacol. 30:1986;212-217.
43. Carstairs J.R., Barnes P.J. Visualization of vasoactive intestinal peptide receptors in human and guinea-pigs lungs. J. Pharmacol. Exp. Ther. 239:1986;249-255.
44. Platou E.S., Smüseth O.A., Retsun H., Rouleau J.L., Chuck L.H.S. Vasodilator and inotropic effects of the antiarrythmic drug melperone. J. Cardiovasc. Pharmacol. 4:1982;645-651.