Synthesis and pharmacological evaluation of some 8- cyanopyrido[3',2':4,5]thieno[3,2-d]triazine derivatives as inhibitors of nitric oxide and eicosanoid biosynthesis

Journal of Medicinal Chemistry

Volumn 42, Issue 22, 1999, Pages 4720-4724

  Quintela, José Ma ^a   Peinador, Carlos ^a   González, Liliana Ma ^a   Riguera, Ricardo ^b   Rioja, Inmaculada ^c   Terencio, Ma Carmen ^c   Ubeda, Amalia ^c   Alcaraz, Ma José ^c  

^a UNIVERSITY OF A CORUÑA   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

7 (N 4' ACETYLPHENYLPIPERAZINO) 8 CYANO 4 CHLOROPYRIDOL[3',2':4,5]THIENO[3,2 D] 1,2,3 TRIAZINE; 8 CYANO 4 (4 METHYLPIPERIDINO) 7 MORPHOLINOPYRIDO [3',2':4,5]THIENOL[3,2 D] 1,2,3 TRIAZINE; ANTIINFLAMMATORY AGENT; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; NITRIC OXIDE; NITRIC OXIDE SYNTHASE INHIBITOR; PROSTAGLANDIN E2; PROSTAGLANDIN INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; IN VITRO STUDY; INFLAMMATION; MOUSE; NONHUMAN; PERITONEUM MACROPHAGE; PROSTAGLANDIN SYNTHESIS; REACTION ANALYSIS;

ANIMALS; CELLS, CULTURED; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; DINOPROSTONE; ENZYME INHIBITORS; ISOENZYMES; MACROPHAGES, PERITONEAL; MICE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE TYPE II; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES; TRIAZINES;

EID: 0033523945     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991085l     Document Type: Article

References (17)

1. Moncada, S.; Higgs, A. The L-arginine-nitric oxide pathway. N. Engl. J. Med. 1993, 329, 2002-2012.
2. MacMicking, J.; Xie, Q.; Nathan, C. Nitric oxide and macrophage function. Annu. Rev. Immunol. 1997, 15, 323-350.
3. Kaur, H.; Halliwell, B. Evidence for nitric oxide-mediated oxidative damage in chronic inflammation. Nitrotyrosine in serum and synovial fluid from rheumatoid patients. FEBS Lett. 1994, 350, 9-12.
4. Móilanen, E.; Vapaatalo, H. Nitric oxide in inflammation and immune response. Ann. Med. 1995, 27, 359-367.
5. Thiemermann, C. The role of arginine: nitric oxide pathways in circulatory shock. Adv. Pharmacol 1994, 28, 45-79.
6. Vane, J. R.; Mitchell, J. A.; Appleton, I.; Tomlison, A.; Bishop-Bailey, D.; Croxtall, J.; Willoughby, D. A. Inducible isoforms of cyclooxygenase and nitric-oxide synthase in inflammation. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 2046-2050.
7. Kang, R. Y.; Freire Moar, J.; Sigal, E.; Chu, C. Q. Expression of cyclooxygenase-2 in human and an animal model of rheumatoid arthritis. Br. J. Rheumatol. 1996, 35, 711-718.
8. Habib, A.; Bernard, C.; Lebret, M.; Créminon, C.; Esposito, B.; Tedgui, A.; Maclouf, J. Regulation of the expression of cyclooxygenase-2 by nitric oxide in rat peritoneal macrophages. J. Immunol. 1997, 158, 3845-3851.
9. Fukuto, J. M.; Chaudhuri, G. Inhibition of constitutive and inducible nitric oxide synthase: potential selective inhibition. Annu. Rev. Pharmacol. Toxicol. 1995, 35, 165-194.
10. Guerrera, F.; Salerno, L.; Sarvà, M. C.; Siracusa, M. A. Synthesis and antifungal activity of pyrido[3′,2′:4,5]thieno[3,2-d]-1,2,3-triazine derivatives. Farmaco 1993, 48, 1725-1733.
11. Wagner, G.; Leistner, S.; Viewer, H.; Krasselt, U.; Prantz, J. Synthese neuer pyrido[3′,2′:4,5]thieno[3,2-d]1,2,3-triazin-derivate als antianaphylaktika. Pharmazie 1993, 48, 514-518.
12. Beck, J. R.; Yahner, J. A. Synthesis of [1]Benzothieno[3,2-d]-v-triazine derivatives. A unique diazonium ion cyclization. J. Org. Chem. 1976, 41, 1733-1734.
13. Quintela, J. M.; Peinador, C.; Veiga, C.; Gonzalez, L.; Botana, L. M.; Alfonso, A.; Riguera, R. Synthesis and antiallergic activity of pyridothienopyrimidines. Bioorg. Med. Chem. 1998, 6, 1911-1925.
14. Misko, T. P.; Schilling, R. J.; Salvemini, D.; Moore, W. M.; Currie, M. G. A fluorometric assay for the measurement of nitrite in biological samples. Anal. Biochem. 1995, 214, 11-16.
15. Moroney, M. A.; Alcaraz, M. J.; Forder, R. A.; Carey, F.; Hoult, J. R. S. Selectivity of neutrophil 5-lipoxygenase and cyclooxygenase inhibition by an antiinflammatory flavonoid glycoside and related aglycone flavonoids. J. Pharm. Pharmacol. 1988, 40, 787-792.
16. Escrig, V.; Ubeda, A.; Ferrándiz, M. L.; Darias, J.; Sanchez, J. M.; Alcaraz, M. J.; Paya, M. Variabilin: a dual inhibitor of human secretory and cytosolic phospholipase A: with antiinflammatory activity. J. Pharmacol. Exp. Ther. 1997, 282, 123-131.
17. Mitchell, J. A.; Sheng, H.; Förstermann, U.; Murad, F. Characterization of nitric oxide synthases in nonadrenergic noncholinergic nerve-containing tissue from the rat anococcygeus muscle. Br. J. Pharmacol. 1991, 104, 289-291.