Synthesis and antiplatelet evaluation of novel aryl-sulfonamide derivatives, from natural safrole

Pharmaceutica Acta Helvetiae

Volumn 73, Issue 6, 1999, Pages 281-292

  Lima, Lídia M ^a   Ormelli, Cláudia B ^a   Brito, Fernanda F ^a   Miranda, Ana L P ^a   Fraga, Carlos A M ^a   Barreiro, Eliezer J ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Antiplatelet activity; Aryl sulfonamide derivatives; Safrole in synthesis; TXA2 antagonists

Indexed keywords

15 HYDROXY 11ALPHA,9ALPHA EPOXYMETHANOPROSTA 5,13 DIENOIC ACID; ADENOSINE DIPHOSPHATE; ANTITHROMBOCYTIC AGENT; ARACHIDONIC ACID; ARYLSULFONIC ACID DERIVATIVE; COLLAGEN; SAFROLE; SULFONAMIDE; THROMBOXANE A2 RECEPTOR BLOCKING AGENT;

ARTICLE; DRUG ACTIVITY; DRUG IDENTIFICATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; THROMBOCYTE AGGREGATION;

ANIMALS; HUMANS; PLATELET AGGREGATION; PLATELET AGGREGATION INHIBITORS; RABBITS; SAFROLE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 0032790228     PISSN: 00316865     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-6865(99)00004-7     Document Type: Article

References (43)

1. Ackerley N., Brewster A.G., Brown G.R., Claeke D.S., Foubister A.J., Griffin S.J., Hudson J.A., Smithers M.J., Whittamore P.R.O. A novel approach to dual-acting thromboxane receptor antagonist/synthase inhibitors based on the link of 1,3-dioxane-thromboxane receptor antagonists and thromboxane synthase inhibitors. J. Med. Chem. 38:1995;1608-1628.
2. 2 receptor antagonists by AM1. Int. J. Quantum Chem.: Quantum Biology Symposium. 22:1995;181-190.
3. Barreiro, E.J., Costa, P.R.R., Barros, P.R.V.R., Queiroz, W.M., 1982. An improved synthesis of indole derivatives related to indomethacin from natural safrole. J. Chem. Res., M, 1142-1165.
4. Barreiro, E.J., Costa, P.R.R., Coelho, F.A.S., Farias, F.M.C., 1985. Prostaglandin analogues: 2. Synthesis of new prostanoid derivatives from safrole isolated from Sassafraz oil. J. Chem. Res., M, 2301-2332.
5. Barreiro E.J., Lima M.E.F. The synthesis and anti-inflammatory properties of a new sulindac analogue synthesized from natural safrole. J. Pharm. Sci. 81:1992;1219-1222.
6. Barrow R.A., Hemscheidt T., Liang J., Paik S., Moore R.E., Tius M.A. Total synthesis of cryptophycins. Revision of the structure of cryptophycins A and C. J. Am. Chem. Soc. 117:1995;2479-2484.
7. Bertele V., De Gaetano G. Potentiation by dazoxiben, a thromboxane synthase inhibitor, of platelet aggregation inhibitory activity of a thromboxane receptor antagonist and of prostacyclin. Eur. J. Pharmacol. 85:1982;331-333.
8. 2. Nature. 315:1985;511-513.
9. Born G.V.R., Cross M.J. The aggregation of blood platelets. J. Physiol. 168:1963;178-181.
10. 2 balance: pathophysiological and therapeutic implications. Br. Med. Bull. 39:1983;271-277.
11. Cabral L.M., Barreiro E.J. The synthesis and analgesic properties of new spiro-isochromanyl acid derivatives synthesized from natural safrol. J. Heterocycl. Chem. 32:1995;959-962.
12. Collington E., Finch H. Thromboxane synthase inhibitors and receptor antagonists. Ann. Rept. Med. Chem. 25:1990;99-108.
13. Fiddler G., Lumley P. Preliminary clinical studies with thromboxane synthase inhibitors and thromboxane receptor blockers (Review). Circulation. 81:1990;69-78.
14. Fitzgerald G.A., Reilly I.A.G., Pedersen A.K. The biochemical pharmacologgy of thromboxane synthase inhibition in man. Circulation. 72:1985;1194-1201.
15. Fraga, C.A.M., 1991. M.Sc. Thesis, Universidade Federal do Rio de Janeiro, Rio de Janeiro, BR.
16. Fraga C.A.M., Barreiro E.J. The synthesis of a new benzothiazine derivative, related to oxicams, synthesized from natural safrole. J. Heterocycl. Chem. 29:1992;1667-1669.
17. Grahan S.L., Hoffman J.M., Gautheron P., Michelson R.S., Scholz T.H., Schwam H., Shepard K.L., Smith A.M., Smith R.L., Sondey J.L. Topically active carbonic anhydrase inhibitors: 3. Benzofuran and indole-2-sulfonamides. J. Med. Chem. 33:1990;749-754.
18. Gresele P., Arnout J., Deckmyn H., Huybrechts E., Pieters G., Vermylen J. Role of proaggregatory and antiaggregatory prostaglandins in homeostasis. J. Clin. Invest. 80:1987;1435-1445.
19. 2 receptor antagonists. Med. Res. Rev. 11:1991;503-579.
20. 2 in health and disease. Fed. Proc. 46:1987;131-158.
21. Hamberg M., Svensson J., Samuelsson B. Thromboxanes: a new group of biologically active compounds derived from prostaglandin endoperoxides. Proc. Natl. Acad. Sci. U.S.A. 72:1975;2994-2998.
22. Hawker and Fréchet, 1990.
23. Jakubowski J.A., Smith G.F., Sall D.J. Future antithrombotic therapy. Ann. Rept. Med. Chem. 27:1992;99-108.
24. 2 receptor antagonists. J. Chem. Inf. Comput. Sci. 34:1994;1014-1018.
25. Kato K., Ohkawa S., Terao S., Terashita Z.I., Nishikawa K. Thromboxane synthetase inhibitors. Design, synthesis and evaluation of a novel series of ω-pyridylalkenoic acids. J. Med. Chem. 28:1985;287-292.
26. Lages A.S., Silva K.C.M., Miranda A.L.P., Fraga C.A.M., Barreiro E.J. Synthesis and pharmacological evaluation of new flosulide analogues, synthesized from natural safrole. Bioorg. Med. Chem. Lett. 8:1998;183-188.
27. Larsen A.A., Lish P.M. A new bio-isostere: alkyl sulphonamidophenethanolamines. Nature. 203:1964;1283-1285.
28. Magnera T.F., Caldwell J.S., Ikuta S., Kebarle P. Solvation of halide anions in dimethyl sulfoxide. Factors involved in enhanced reactivity of negative ions in dipolar aprotic solvents. J. Am. Chem. Soc. 106:1984;6140-6145.
29. 2 and prostacyclin. Pharmacol. Rev. 30:1979;293-297.
30. 2. Fed. Proc. 46:1987;133-138.
31. Ong H.H., Allen R.C. Trends and perspectives. Ann. Rept. Med. Chem. 24:1988;295-301.
32. Patani G.A., LaVoie E.J. Bioisosterism: a rational approach in drug design. Chem. Rev. 96:1996;3147-3176.
33. 2 receptor antagonists. A new therapeutic principle. Stroke. 21:1990;139-142.
34. Patscheke H., Stegmeyer K. Investigations on a selective non-prostanoid thromboxane antagonist, BM 13.177, in human platelets. Thromb. Res. 33:1984;277-280.
35. Perreira et al., 1989.
36. Prous, J.R., 1994. Antiplatelet Therapy. The Year's Drug News. In: Prous, J.R. (Ed.), Prous Science, pp. 200-210.
37. 2 receptor antagonists. Eur. J. Med. Chem. 30:1995;403-410.
38. Scherrer, R.A., 1974. Aryl and heteroarylalkanoic acids and related compounds. In: Scherrer, R.A., White, H. (Eds.), Anti-inflammatory Agents: chemistry and pharmacology, Vol. 1, Academic Press, New York, pp. 91-127.
39. Silva E.F., Barreiro E.J. The synthesis and anti-inflammatory activity of 1-alkyl-isochroman-1-yl acetic acids derivatives. J. Braz. Chem. Soc. 4:1993;40-44.
40. 2 receptor antagonists and synthetase inhibitors. J. Med. Chem. 37:1994;22-29.
41. 2 receptor antagonist. Naunyn-Schmiedeberg's Arch. Pharmacol. 322:1986;1-3.
42. Testa, B., 1995. Drug metabolism. In: Wolff, M.E. (Ed.), Burger's Medicinal Chemistry and Drug Discovery Vol. 1, Principles and Practice. Wiley, New York, pp. 129-180.
43. 2 synthase inhibition alone and in combination: comparison of anti-aggregatory efficacy in human platelets. Br. J. Pharmacol. 102:1991;497-505.