Syntheses of some sulfur-containing polyunsaturated fatty acids as potential lipoxygenase inhibitors

Synthetic Communications

Volumn 37, Issue 22, 2007, Pages 4005-4015

  Flock, Solveig ^a   Holmeide, Anne Kristin ^b   Skattebøl, Lars ^b  

^a NORWEGIAN UNIVERSITY OF LIFE SCIENCES   (Norway)

^b UNIVERSITY OF OSLO   (Norway)

Author keywords

5 lipoxygenase; Dicyclohexylborane; Polyunsaturated fatty acids; Sulfur containing fatty acids

Indexed keywords

1 (3 THIENYL) 4,7,10,13 HEXADECATETRAEN 1 YNE; 1 (3 THIENYL) 4,7,10,13,16 HEXADECAPENTAENE; 4 (4,7,10,13 HEXADECATETRAEN 1 YNYL) 2 (1,3 DIOXOLANYL)THIOPHENE; 4 (4,7,10,13 HEXADECATETRAEN 1 YNYL)THIOPHENE 2 CARBOXALDEHYDE; 4 (4,7,10,13 HEXADECATETRAEN 1 YNYL)THIOPHENE 2 CARBOXYLIC ACID; 4,7,10,13 HEXADECATETRAEN 1 YNE; 4,7,10,13,16 NONADECAPENTAEN 1 YNE; CERVONIC ACID; EICOSA 5,8,11,14,17 PENTAENOIC ACID; ETHYL 5 THIA 9,12,15,18 HENEICOSAPENTAEN 6 YNOATE; LIPOXYGENASE INHIBITOR; METHYL 3 (4 BROMO 2 THIENYL)PROPANOATE; METHYL 3 [4 (ALL Z 4,7,10,13,16 HEXADECAPENTAENYL) 2 THIENYL]PROPANOATE; METHYL 3 THIA 7,10,13,16,19 DOCOSAPENTAEN 4 YNOATE; POLYUNSATURATED FATTY ACID; SULFUR; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; DRUG DETERMINATION; DRUG SYNTHESIS;

EID: 36348945083     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701575053     Document Type: Article

References (16)

1. (a) Henderson, W. R., Jr. The role of leukotrienes in inflammation. Ann. Intern. Med. 1994, 121, 684-697;
2. (b) Fitzpatrick, F. A.; Lepley, R.; Orning, L.; Duffin, K. Effects of leukotriene A4 on nutrophil activation. Ann. NY Acad. Sci. 1994, 714, 64-74.
3. Drazen, J. M.; Israel, E.; ÓByrne, P. M. Drug Therapy 1999, 340, 197-206.
4. Kinsella, J. E. B.; Lokesh, B.; Stone, R. A. Dietary n-3 polyunsaturated fatty acids and amelioration of cardiovascular disease: possible mechanisms. Am. J. Clin. Nutr. 1990, 52, 1-28.
5. Horrobin, D. F. Abnormal membrane concentrations of 20 and 22-carbon essential fatty acids: A common link between risk factors and coronary and peripheral vascular disease? Prostaglandins Leukotrienes Essential Fatty Acids 1995, 53, 385-396.
6. Corey, E. J.; Cashman, J. R.; Eckrich, T. M.; Corey, D. R. A new class of irreversible inhibitors of leukotriene biosynthesis. J. Am. Chem. Soc. 1985, 107, 713-715.
7. Hanko, R.; Hammond, M. D.; Fruchtmann, R.; Pfitzner, J.; Place, G. A. Design, synthesis, and 5-leukotriene-inhibiting properties of 1-thio-substituted butadienes. J. Med. Chem. 1990, 33, 1163-1170.
8. 2 inhibitors. J. Chem. Soc., Perkin Trans. 1 2000, 2271-2276.
9. Flock, S.; Lundquist, M.; Skattebøl, L. Syntheses of some polyunsaturated sulfur- and oxygen-containing fatty acids related to eicosapentaenoic and docosahexaenoic acids. Acta Chem. Scand. 1999, 53, 436-445.
10. 2, block TNF-induced activation of transcription factor nuclear factor-κB and expression of ICAM-1. Immunology 1998, 161, 3421-3430.
11. Ringbom, T.; Huss, U.; Stenholm, A.; Flock, S.; Skattebøl, L.; Perera, P.; Bohlin, L. Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J. Nat. Prod. 2001, 64, 745-749.
12. Corey, E. J.; Fuchs, P. L. A synthetic method for formyl-ethynyl conversion. Tetrahedron Lett. 1972, 3769-3772.
13. Brudermüller, M.; Musso, H. Synthesis of all-cis-1,4,7,10- cyclododecatetraene. Angew. Chem., Int. Ed. Engl. 1988, 27, 298-299.
14. De la Rosa, M. A.; Velarde, E.; Guzman, A. Cross-coupling reactions of monosubstituted acetylenes and aryl halides catalyzed by palladium on charcoal. Synth. Commun. 1990, 20, 2059-2064.
15. Lawesson, S. O. A new method of preparing 2,4-dibromothiophene and its Grignard and lithium reagents. Arkiv Kemi 1957, 11, 317-324.
16. Johnson, A. L. Syntheses of the three isomeric ortho-substituted phenylthienyl benzoic acids. J. Org. Chem. 1976, 41, 1320-1324.