Nitric oxide donor β2-agonists: Furoxan derivatives containing the fenoterol moiety and related furazans

Journal of Medicinal Chemistry

Volumn 50, Issue 20, 2007, Pages 5003-5011

  Federica Buonsanti, M ^a   Bertinaria, Massimo ^a   Di Stilo, Antonella ^a   Cena, Clara ^a   Fruttero, Roberta ^a   Gasco, Alberto ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BETA 2 ADRENERGIC RECEPTOR STIMULATING AGENT; FENOTEROL; FURAZAN DERIVATIVE; FUROXAN DERIVATIVE; NITRIC OXIDE; NITRIC OXIDE DONOR; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; AORTA MEDIA; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; GUINEA PIG; LIVER MICROSOME; MALE; NONHUMAN; RAT; SMOOTH MUSCLE RELAXATION; STRUCTURE ACTIVITY RELATION; TRACHEA MUSCLE;

ANIMALS; ANTIOXIDANTS; AORTA; FENOTEROL; GUINEA PIGS; MALE; MICROSOMES, LIVER; MUSCLE CONTRACTION; MUSCLE RELAXATION; MUSCLE, SMOOTH; NITRIC OXIDE; NITRIC OXIDE DONORS; OXADIAZOLES; RATS; RATS, WISTAR; RECEPTORS, ADRENERGIC, BETA-2; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRACHEA; VASODILATOR AGENTS;

EID: 34948888188     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0704595     Document Type: Article

References (26)

1. Waldeck, B. β-Adrenoreceptor Agonists and Asthma - 100 Years of Development. Eur. J. Pharmacol. 2002, 445, 1-12.
2. Guussen, A.; Jaworska, M.; Schärling, B.; van Zwoll, D.; Schultze-Werninghaus, G. β-2-Agonists have Antioxidant Function In Vitro. Respiration 1997, 64, 16-22.
3. Kerwin, J. F., Jr.; Heller, M. The Arginine-Nitric Oxide Pathway: A Target for New Drugs. Med. Res. Rev. 1994, 14, 23-74.
4. Matera, M. G. Nitric Oxide and Airways. Pulm. Pharmacol. Ther. 1998, 11, 341-348.
5. Nevin, B. J.; Broadley, K. J. Nitric Oxide in Respiratory Diseases. Pharmacol. Ther. 2002, 95, 259-293.
6. Keeble, J. E.; Moore, P. K. Pharmacology and Potential Therapeutic Applications of Nitric Oxide-Releasing Nonsteroidal Anti-Inflammatory and Related Nitric Oxide-Donating Drugs. Br. J. Pharmacol. 2002, 137, 295-310.
7. Lagente, V.; Advenier, C. New Nitric-Oxide Drugs for the Treatment of Airway Diseases. Curr. Opin. Invest. Drugs 2004, 5, 537-541.
8. Ricciardolo, F. L. M.; Nijkamp, F. P.; Folkerts, G. Nitric Oxide Synthase (NOS) as Therapeutic Target for Asthma and Chronic Obstructive Pulmonary Disease. Curr. Drug Targ. 2006, 7, 721-735.
9. Queen, L. R.; Ferro, A. β-Adrenergic Receptors and Nitric Oxide Generation in the Cardiovascular System. Cell. Mol. Life Sci. 2006, 63, 1070-1083.
10. Ritter, J. M.; Ferro, A.; Chowienczyk, P. J. Relation between /3-Adrenoreceptor Stimulation and Nitric Oxide Synthesis in Vascular Control. Eur. J. Clin. Pharmacol. 2006, 62, 109-113.
11. Goodman, L. S., Gilman, A. G., Limbird, L. E., Milinoff, P. B., Ruddon, R. W. In The pharmacological basis of therapeutics, 11th edition; Pergamon Press: New York, 2006.
12. Billica, H. R.; Adkins, H. Catalyst, Raney Nickel, W-6. Organic Syntheses; Wiley & Sons: New York, 1955; Collect. Vol. 3, pp 176-180.
13. Hoover, F. V.; Haas, H. B. Synthesis of Paredrine and Related Compounds. J. Org. Chem. 1947, 12, 501-505.
14. Sorba, G.; Medana, C.; Fruttero, R.; Cena, C.; Di Stilo, A.; Galli, U.; Gasco, A. Water Soluble Furoxan Derivatives as NO Prodrugs. J. Med. Chem. 1997, 40, 463-469;
15. 1997, 40, 2288.
16. Hwang, T.-L.; Wu, C.-C.; Teng, C.-M. Comparison of Two Soluble Guanylyl Cyclase Inhibitors, Methylene Blue and ODQ, on Sodium Nitroprusside-Induced Relaxation in Guinea-Pig Trachea. Br. J. Pharmacol. 1998, 125, 1158-1163.
17. Boschi, D.; Di Stilo, A.; Cena, C.; Lolli, M.; Fruttero, R.; Gasco, A. Studies on Agents with Mixed NO-Dependent Vasodilating and β-Blocking Activities. Pharm. Res. 1997, 14, 1750-1758.
18. Heffner, J. E.; Repine, J. E. Pulmonary Strategies of Antioxidant Defense. Am. Rev. Respir. Dis. 1989, 140, 531-554.
19. Antolovich, M.; Prenzler, P. D.; Patsalides, E.; McDonald, S.; Robards, K. Methods for Testing Antioxidant Activity. Analyst 2002, 127, 183-198.
20. Farrar, W. V. The 3,4-Bisarenesulfonylfuroxans. J. Chem. Soc. 1964, 904-906.
21. Boschi, D.; Di Stilo, A.; Cena, C.; Lolli, M.; Fruttero, R.; Gasco, A. Studies on Agents with Mixed NO-Dependent Vasodilating and β-Blocking Activities. Pharm. Res. 1997, 14, 1750-1758.
22. Pollet, P.; Gellin, S. Tetronic Acids and Derivatives; part VI. A Convenient Synthesis of New 4-Oxo-2-phenyl-2H-4,6-dihydrofuro-[3,4-d]thiazole and 4-Oxo-4,6-dihydrofuro[3,4-c]furazan System. Synthesis 1979, 12, 977-979.
23. Di Stilo, A.; Visentin, S.; Cena, C.; Gasco, A. M.; Ermondi, G.; Gasco, A. New 1,4 Dihydropyridines Conjugated to Furoxanyl Moieties, Endowed with Both Nitric Oxide-like and Calcium Channel Antagonist Vasodilator Activities. J. Med. Chem. 1998, 41, 5393-5401.
24. Gasco, A. M.; Fruttero, R.; Sorba, G.; Gasco, A.; Budriesi, R.; Chiarini, A. Synthesis and Cardiovascular Properties of Furazanyl-1,4-dihydropyridines and of Furoxanyl Analogues. Arzneim.-Forsch. 1992, 42 (11), 921-925.
25. European Pharmacopoeia, 5th ed.; Council of Europe: Strasbourg Cedex, France, 2006.
26. Schmidt, K; Mayer, B. Determination of NO with a Clark-Type Electrode. In Methods in Molecular Biology, vol. 100. Nitric oxide Protocols; Titheradge, M. A., Ed.; Humana Press, Inc.: Totowa, NJ, 1998; pp 101-109.