Substituted isoquinolines and quinazolines as potential antiinflammatory agents. Synthesis and biological evaluation of inhibitors of tumor necrosis factor α

Journal of Medicinal Chemistry

Volumn 42, Issue 19, 1999, Pages 3860-3873

  Chao, Qi ^a   Deng, Lynn ^a   Shih, Hsiencheng ^a   Leoni, Lorenzo M ^a   Genini, Davide ^a   Carson, Dennis A ^a   Cottam, Howard B ^a  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (6 AMINO 4 OXOQUINAZOLIN 3 YL)BUTANOIC ACID ETHYL ESTER; 4 (7 AMINO 4 OXOQUINAZOLIN 3 YL)BUTANOIC ACID ETHYL ESTER; ANTIINFLAMMATORY AGENT; INTERLEUKIN 1; ISOQUINOLINE DERIVATIVE; QUINAZOLINE DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; TUMOR NECROSIS FACTOR ALPHA ANTAGONIST; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IMMUNOMODULATION; INHALATIONAL DRUG ADMINISTRATION; INTRAPERITONEAL DRUG ADMINISTRATION; LUNG LAVAGE; MALE; MONONUCLEAR CELL; MOUSE; NONHUMAN; NORMAL HUMAN; PNEUMONIA; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-INFLAMMATORY AGENTS; HUMANS; ISOQUINOLINES; LEUKOPENIA; LIPOPOLYSACCHARIDES; MALE; MICE; MICE, INBRED BALB C; MODELS, CHEMICAL; PHOTOAFFINITY LABELS; PHOTOCHEMISTRY; QUINAZOLINES; RETROSPECTIVE STUDIES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 0033598323     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9805900     Document Type: Article

References (26)

1. Isomaki, P.; Punnonen, J. Pro- and Antiinflammatory Cytokines in Rheumatoid Arthritis. Ann. Med. 1997, 29, 499-507.
2. Mitzutani, H.; Ohmoto, Y.; Mitzutani, T.; Murata, M.; Shimizu, M. Role of Increased Production of Monocytes TNF-alpha, IL-1-beta and IL-6 in Psoriasis: Relation to Focal Infection, Disease Activity and Responses to Treatment. J. Dermatol. Sci. 1997, 14, 145-153.
3. Stokkers, P. C. F.; Camoglio, L.; Van Deventer, S. J. H. Tumor Necrosis Factor (TNF) in Inflammatory Bowel Disease: Gene Polymorphisms, Animal Models, and Potential for Anti-TNF Therapy. J. Inflamm. 1995-1996, 47, 97-103.
4. Bonfield, T. L.; Pansuka, J. R.; Konstan, M. W.; Hilliard, K. A.; Hilliard, J. B.; Ghnaim, H.; Berger, M. Inflammation Cytokines in Cystic Fibrosis Lungs. Am. J. Respir. Crit. Care Med. 1995, 152, 2111-2118.
5. Cottam, H. B.; Shih, H.; Tehrani, L. R.; Wasson, D. B.; Carson, D. A. Substituted Xanthines, Pteridinediones, and Related Compounds as Potential Antiinflammatory Agents. Synthesis and Biological Evaluation of Inhibitors of Tumor Necrosis Factor α. J. Med. Chem. 1996, 39, 2-9.
6. Horning, D. E.; Lacasse, G.; Muchowski, J. M. Isocarbostyrils. I. Electrophilic Substitution Reactions. Can. J. Chem. 1971, 49, 2785-2796.
7. Tamao, K.; Kodama, S.; Nakajima, I.; Kumada, M. Nickel-Phosphine Complex-Catalyzed Grinard Coupling - II. Grinard Coupling of Hereocyclic Compounds. Tetrahedron 1982, 38, 3347-3354.
8. DeRuiter, J.; Brubaker, A. N.; Millen, J.; Riley, T. N. Design and Synthesis of 2-(Arylamino)-4(3H)-quinazolinones as Novel Inhibitors of Rat Lens Aldose Reductase J. Med. Chem. 1986, 29, 627-629.
9. Temple, C., Jr.; Thorpe, M. C.; Coburn, W. C., Jr.; Montgomery, J. A. Studies on the Azidoazomethine-Tetrazole Equilibrium. IV. Azidopurines. J. Org. Chem. 1966, 31, 935-938.
10. Bridges, A. J.; Zhou, H.; Cody, D. R.; Rewcastle, G. W.; McMichael, A.; Showalter, H. D. H.; Fry, D. W.; Kraker, A. J.; Denny, W. A. Tyrosine Kinase Inhibitors. 8. An Unusually Steep Structure-Activity Relationship for Analogues of 4-(3-Bromoanilino)-6,7-dimethoxy-qumazoline (PD 153035), a Potent Inhibitor of the Epidermal Growth Factor Receptor J. Med. Chem. 1996, 39, 267-276.
11. LeMahieu, R. A.; Carson, M.; Nason, W. C.; Parrish, D. R.; Welton, A. F.; Baruth, H. W.; Yaremko, B. (E)-3-(4-Oxo-4H-quinazolin-3-yl)-2-propenoic Acids, a New Series of Antiallergy Agents. J. Med. Chem. 1983, 26, 420-425.
12. Node, M.; Nishide, K.; Sai, M.; Ichikawa, K.; Fuji, K.; Fujita, E. Aluminium Halide-Thiol System: A Useful Reagent for Demethylation of Aliphatic and Aromatic Methyl Ethers and Demethylenation of Methylenedioxy Compounds. Chem. Lett. 1979, 97-98.
13. Brown, D. J. Quinazolines, Supplement I. In The Chemistry of Heterocyclic Compounds; Taylor, E., Weissberger, A., Eds.; John Wiley & Sons: New York, 1996; pp 321-366.
14. Foster, R. H.; Leonard, N. J. Synthesis of Prox-Benzoisoallopurinol. J. Org. Chem. 1980, 45, 3072-3077.
15. Lichtenthaler, F. W.; Cuny, E. Synthesis of A [3,4-f]-Linked Pyrazoloquinazolinone. Heterocycles 1981, 15, 1053-1059.
16. Cuny, E.; Lichtenthaler, F. W.; Moser, A. Benzologs of Allopurinol: Synthesis of Pyrazolo[4,3-g] and [3,4-f]Quinazolinones Tetrahedron Lett. 1980, 21, 3029-3032.
17. Gupta, C. M.; Bhaduri, A. P.; Khanna, N. M. Biologically Active Imidazolo[5,6]quinazolinones. Ind. J. Chem. 1969, 7, 1166-1167.
18. Bouchet, M.-J.; Goeldner, M. Photochemical Labeling: Can Photoaffinity Labeling Be Differentiated From Site-Directed Photochemical Coupling? Photochem. Photobiol. 1997, 65, 195-200.
19. Maillard, J.; Bénard, M.; Vincent, M.; Vo-Van-Tri; Jolly, R.; Morin, R.; Menillet, C.; Benharkate, Mme. Dérivés de la (3H)-Quinazolinone-4 Doués de Propriétés Antiinflammatoires I. Dérivés Substitutés en 3 et en 1. (Derivatives of 3H-Quinazolin-4-one with Antiinflammatory Properties I. Derivatives Substituted in the 3 and 1 Positions.) Chim. Thér. 1967, 2, 202-212.
20. Maillard, J.; Bénard, M.; Vincent, M.; Vo-Van-Tri; Jolly, R.; Morin, R.; Benharkate, Mme, Menillet, C. Dérivés de la (3H)-Quinazolinone-4 Doués de Propriétés Antiinflammatoires II. Dérivés Substitutés Dans le Noyau Aromatique et Produit Voisin. (Derivatives of 3H-Quinazolin-4-one with Antiinflammatory Properties II. Derivatives Substituted in the Aromatic Ring and Related Products.) Chim. Thér. 1967, 2, 2231-239.
21. Lazer, E. S.; Sorcek, R.; Cywin, C. L.; Thome, D.; Possanza, G. J.; Graham, A. G.; Churchhill, L. Antiinflammatory 2-Benzyl-4-sulfonyl-4H-isoquinoline-1,3-diones: Novel Inhibotors of COX-2. Bioorg. Med. Chem. Lett. 1998, 8, 1181-1186.
22. Milchne, W. F.; Schroeder, J. D.; Guiles, J. W.; Tresasurywala, A. M.; Weigelt, C. A.; Stansberry, M. F.; McAvoy, E.; Shah, C. R.; Baine, Y.; Sawutz, D. G. Novel Inhibitors of the Nuclear Factor of Activated T Cells (NFAT)-mediated Transcription of Beta-Galactosidase: Potebtial Immunosupressive and Antiinflammatory Agents. J. Med. Chem. 1995, 38, 2557-2569.
23. Wilhelm, R.; Chin, R.; Loe, B.; Axt, S.; Alvarez, B.; Fong, A. N-1-Aryl-Quinazolinediones: Potent and Selective Inhibitors of Phosphodiesteraee (PDE IV). Abstract of Papers, 207th National Meeting of the Americam Chemical Society, San Diego, CA, March 13-17, 1994; American Chemical Society: Washington, DC, 1994; Vol 207, n. 1-2, MEDI 120.
24. He, W.; Huang, F.-C.; Hanney, B.; Souness, J.; Miller, B.; Liang, G.; Mason, J.; Djuric, S. Novel Cyclic Compounds as Potent Phosphodiesterase 4 Inhibitors. J. Med. Chem. 1998, 41, 4216-4223.
25. Perkins, D. J.; Kniss, D. A. Tumor Necrosis Factor-alpha Mediates Sustained Cyclooxygenase-2 Expression: Attenuation by Dexamethazone and NSAIDs. Prostaglandins 1997, 54, 727-743.
26. Gonçalves de Moraes, V. L.; Vargaftig, B. B.; Lefort, J.; Meager, A.; Chignard, M. Effect of Cyclo-oxygenase Inhibitors and Modulators of Cyclic AMP Formation on Lipopolysaccharide-Induced Neutrophil Infiltration in Mouse Lung. Brit. J. Pharmacol. 1996, 117, 1792-1796.