6-Substituted purines as inhibitors of 15-lipoxygenase; a structure-activity study

Archiv der Pharmazie

Volumn 338, Issue 4, 2005, Pages 159-166

  Bråthe, Anders ^a   Gundersen, Lise Lotte ^a   Malterud, Karl E ^a   Rise, Frode ^a  

^a UNIVERSITY OF OSLO   (Norway)

Author keywords

15 Lipoxygenase; 6 Substituted purines; Enzyme inhibition; Pd catalyzed couplings

Indexed keywords

2 (4 CHLOROPHENYL) 6 (2 PHENYLETHEN 1 YL) 9 PHENYLMETHYL 9H PURINE; 2 (4 METHOXYPHENYL) 6 (2 PHENYLETHEN 1 YL) 9 PHENYLMETHYL 9H PURINE; 2 METHOXY 6 (2 PHENYLETHEN 1 YL) 9 PHENYLMETHYL 9H PURINE; 2 METHYL 6 (2 PHENYLETHEN 1 YL) 9 PHENYLMETHYL 9H PURINE; 6 (2 PHENYLCYCLOPROP 1 YL) 1H PURINE; 6 (2 PHENYLCYCLOPROP 1 YL) 9 (TETRAHYDRO 2H PYRAN 2 YL) 9H PURINE; 6 (2 PHENYLCYCLOPROP 1 YL) 9 PHENYLMETHYL 9H PURINE; 6 (2 PHENYLETHEN 1 YL) 9 PHENYLMETHYL 8H PURIN 8 ONE; 6 PHENYLMETHYL 1H PURINE; 6 PHENYLMETHYL 9 (TETRAHYDRO 2H PYRAN 2 YL) 9H PURINE; 6,8 DICHLORO 9 PHENYLMETHYL 9H PURINE; 7 METHYL 6 (2 PHENYLETHEN 1 YL) 7H PURINE; 8 CHLORO 6 (2 PHENYLETHEN 1 YL) 9 PHENYLMETHYL 9H PURINE; 8 METHYL 6 (2 PHENYLETHEN 1 YL) 9 PHENYLMETHYL 9H PURINE; 9 (1 METHYLETHYL) 6 (2 PHENYLETHEN 1 YL) 9H PURINE; 9 [(METHYLTHIO)METHYL] 6 (PHENYLETHEN 1 YL) 9H PURINE; 9 METHYL 6 (2 PHENYLETHEN 1 YL) 9H PURINE; 9 PHENYL 6 (2 PHENYLETHEN 1 YL) 9H PURINE; ARACHIDONATE 15 LIPOXYGENASE; CARBON; CYCLOPROPANE DERIVATIVE; LOW DENSITY LIPOPROTEIN; PALLADIUM; PHENYL GROUP; PURINE DERIVATIVE; QUERCETIN; UNCLASSIFIED DRUG;

ARTICLE; ATHEROSCLEROSIS; BINDING AFFINITY; DRUG SYNTHESIS; ENZYME INHIBITION; PRIORITY JOURNAL; SOYBEAN; STRUCTURE ACTIVITY RELATION;

ARACHIDONATE 15-LIPOXYGENASE; LIPOXYGENASE INHIBITORS; PURINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 19544377674     PISSN: 03656233     EISSN: None     Source Type: Journal    
DOI: 10.1002/ardp.200400951     Document Type: Article

References (29)

1. A. Bråthe, L.-L. Gundersen, F. Rise, A. B. Eriksen, A. V. Vollsnes, L. Wang, Tetrahedron 1999, 55, 211-228.
2. G. Andresen, B. Dalhus, A. B. Eriksen, L.-L. Gundersen, F. Rise, J. Chem. Soc., Perkin Trans. 2001, 1, 1662-1672.
3. A. Bråthe, G. Andresen, L.-L. Gundersen, K. E. Malterud, F. Rise, Bioorg. Med. Chem. 2002, 10, 1581-1586.
4. A. Bråthe, L.-L. Gundersen, J. Nissen-Meyer, F. Rise, B. Spilsberg, Bioorg. Med. Chem. Lett. 2003, 13, 877-880.
5. D. Steinberg, J. Clin. Invest. 1999, 103, 1487-1488.
6. S. M. Sendobry, J. A. Cornicelli, K. Welch, T. Bocan, B. Tait, B. K. Trivedi, N. Colbry, R. D. Dyer, S. J. Feinmark, A. Daughterly, Br. J. Pharmacol. 1997, 120, 1199-1206.
7. U. P. Kelavkar, C. Cohen, H. Kamitani, T. E. Eling, K. F. Badr, Carcinogenesis 2000, 21, 1777-1787.
8. U. P. Kelavkar, J. B. Nixon, C. Cohen, D. Dillehay, T. E. Eling, K. F. Badr, Carcinogenesis 2001, 22, 1765-1773.
9. P. Dar, D. Strassburger, A. Shaish, H. Levkovitz, R. Halperin, D. Harats, Gynecol. Obstetr. Invest. 2001, 52, 18-21.
10. N. Shimizu, S. Watanabe, Y. Tsuno, Chem. Lett. 1983, 13, 1877-1878.
11. A. T. Øverås, A. K. Bakkestuen, L.-L. Gundersen, F. Rise, Acta Chem. Scand. 1997, 51, 1116-1124.
12. J. M. N Nolsøe, L.-L. Gundersen, F. Rise, Synth. Commun. 1998, 28, 4303-4315 and references therein.
13. J. M. J. Nolsøe, L.-L. Gundersen, F. Rise, Acta Chem. Scand. 1999, 53, 366-372.
14. For some recent examples, see for instance: K. Hirota, K. Kazaoka, I. Niimoto, H. Sajiki, Org. Biomol. Chem. 2003, 1, 1354-1365;
15. M. Hocek, D. Hockoá, H. Dvoráková, Synthesis 2004, 899-894.
16. R. K. Robins, E. F. Godefroi, E. C. Taylor, L. R. Lewis, A. Jackson, J. Am. Chem. Soc. 1961, 83, 2574-2579.
17. A. K. Bakkestuen, A. J. Aasen, H. Øverås, F. Rise, Tetrahedron 1994, 50, 9743-9756.
18. M. Hocek, A. Holy, I. Votruba, H. Dvoráková, J. Med. Chem. 2000, 43, 1817-1825.
19. G. Langli, L.-L. Gundersen, F. Rise, Tetrahedron 1996, 52, 5625-5638.
20. A. K. Bakkestuen, L.-L. Gundersen, G. Langli, F. Liu, J. M. J. Nolsøe, Bioorg. Med. Chem. Lett. 2000, 10, 1207-1210.
21. E. C. Taylor, S. F. Martin, J. Am. Chem. Soc. 1974, 96, 8095-8102.
22. R. J. Lang, L. Brandsma, Synth. Commun. 1998, 28, 225-232.
23. M. Cesnek, A. Holy, M. Masojidkova, Tetrahedron 2002, 58, 2985-2996.
24. J. W. Labadie, J. K. Stille, J. Am. Chem. Soc. 1983, 105, 6129-6137.
25. B. Y. Kim, J. B. Ahn, H. W. Lee, S. K. Kang, J. H. Lee, J. S. Shin, S. K. Ahn, C. I. Hong, S. S. Yoon, Eur. J. Med. Chem. 2004, 39, 433-447.
26. J. L. Kelley, R. M. Bullock, M. P. Krochmal, E. W. McLean, J. A. Linn, M. J. Durcan, B. R. Cooper, J. Med. Chem. 1997, 40, 3207-3216.
27. A. K. Bakkestuen, L.-L. Gundersen, Tetrahedron Lett. 2003, 44, 3359-3362.
28. K. E. Malterud, K. M. Rydland, J. Agr. Food Chem. 2000, 48, 5576-5580.
29. K. E. Malterud, T. L. Farbrot, A. E. Huse, R. B. Sund, Pharmacology 1993, 47, Suppl 1, 77-85.