Synthesis of novel benzoquinones with anti-inflammatory activity

Letters in Drug Design and Discovery

Volumn 6, Issue 3, 2009, Pages 172-177

  Sagnou, Marina ^a,c   Strongilos, Alexandros ^b   Hadjipavlou Litina, Dimitra ^a,c   Couladouros, Elias A ^d  

^a Institute of Biology   (Greece)

^b PRO ACTINA SA   (Greece)

^c ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^d AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

Benzoquinones; Inflammation; LOX; Psoriasis; Radical scavengers; Shikonin

Indexed keywords

BENZOQUINONE DERIVATIVE; HYDROXYL RADICAL; INDOMETACIN; LIPOXYGENASE; NORDIHYDROGUAIARETIC ACID; SHIKONIN; TROLOX C;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; NONHUMAN; PAW EDEMA; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION;

EID: 64949186474     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018009787847792     Document Type: Article

References (33)

1. Fürstenberger, G.; Krieg, P.; Müller-Decker, K.; Habenicht, A.J. What are cyclooxygenases and lipoxygenases doing in the driver's seat of carcinogenesis? Int. J. Cancer, 2006, 119, 2247-2254.
2. Jatana, M.; Giri, S.; Ansari, M.A.; Elango, C.; Singh, A.K.; Singh, I.; Khan, M. Inhibition of NF-kappaB activation by 5-lipoxygenase inhibitors protects brain against injury in a rat model of focal cerebral ischemia. J. Neuroinflammation, 2006, 3, 12-24.
3. Rossoni, G.; Sala, A.; Berti, F.; Testa, T.; Buccellati, C.; Molta C.; Muller-Peddinghaus, R.; Maclouf, J.; Folco, G.C. Myocardial protection by the leukotriene synthesis inhibitor BAY X1005: importance of transcellular biosynthesis of cysteinyl-leukotrienes. J. Pharmacol. Exp. Ther., 1996, 276, 335-341.
4. van Leyen, K.; Kim, H.Y.; Lee, S.R.; Jin, G.; Arai, K.; Lo, E.H. Baicalein and 12/15- lipoxygenase in the ischemic brain. Stroke, 2006, 37, 3014-3018.
5. Rubin, P.; Mollison, K.W. Pharmacotherapy of diseases mediated by 5- lipoxygenase pathway eicosanoids. Prostaglandins Other Lipid Mediat., 2007, 83, 188-197.
6. Chu, L.S.; Fang, S.H.; Zhou, Y.; Yu, G.L.; Wang, M.L.; Zhang, W.P.; Wei, E.Q. Minocycline inhibits 5-lipoxygenase activation and brain inflammation after focal cerebral ischemia in rats. Acta Pharmacol. Sin., 2007, 28, 763.
7. Klickstein, L.B.; Shapleigh, C.; Goetzl, E.J. Lipoxygenation of arachidonic acid as a source of polymorphonuclear leukocyte chemotactic factors in synovial fluid and tissue in rheumatoid arthritis and spondyloarthritis. J. Clin. Invest., 1980, 66, 1166-1170.
8. Araico, A.; Terencio, M.C.; Alcaraz, M.J.; Domínguez, J.N.; León, C.; Ferrándiz, M.L. Evaluation of the anti-inflammatory and analgesic activity of Me-UCH9, a dual cyclooxygenase-2/5- lipoxygenase inhibitor. Life Sci., 2007, 80, 2108-2117.
9. Burka, J.F.; Paterson, N.A. Evidence for lipoxygenase pathway involvement in allergic tracheal contraction. Prostaglandins, 1980, 19, 499-515.
10. Berger, W.; De Chandt, M.T.; Cairns, C.B. Zileuton: clinical implications of 5-Lipoxygenase inhibition in severe airway disease. Int. J. Clin. Pract., 2007, 61, 663-676.
11. Steele, V.E.; Holmes, C.A.; Hawk, E.T.; Kopelovich, L.; Lubet, R.A.; Crowell, J.A.; Sigman, C.C.; Kelloff, G.J. Lipoxygenase inhibitors as potential cancer chemopreventives. Cancer Epidemiol. Biomarkers Prev., 1999, 8, 467-483.
12. Steinhilber, D. 5-Lipoxygenase: a target for antiinflammatory drugs revisited. Curr. Med. Chem., 1999, 6, 71-85.
13. a) Federico, A.; Morgillo, F.; Tuccillo, C.; Ciardiello, C.; Loguercio, F. Chronic inflammation and oxidative stress in human carcinogenesis. Int. J. Cancer, 2007, 121, 2381-6;
14. b) Kökçam, B.; Nazirog, M. Antioxidants and lipid peroxidation status in the blood of patients with psoriasis. Clinica Chimica Acta, 1999, 289, 23-31.
15. Young, R.N. Inhibitors of 5-lipoxygenase: a therapeutic potential yet to be fully realized? Eur. J. Med. Chem., 1999, 34, 671-685.
16. Julemont, F.; Dogne, J.M.; Laeckmann, D.; Pirotte, B.; de Leval, X. Recent developments in 5lipoxygenase inhibitors. Expert Opin. Ther. Pat., 2003, 13, 1-13.
17. Papageorgiou, V.P.; Assimopoulou, A.N.; Couladouros, E.A.; Hepworth, D.; Nicolaou, K.C. The chemistry and biology of alkannin, shikonin, and related naphthazarin natural products. Angew. Chem., Int. Ed., 1999, 38, 270-300.
18. Yang, F.; Chen, Y.; Duan, W.; Zhang, C.; Zhu, H.; Ding, J. SH-7, a new synthesized shikonin derivative, exerting its potent antitumor activities as a topoisomerase inhibitor. Int. J. Cancer, 2006, 119, 1184-1193.
19. Ana, S.; Parka, Y.D.; Paikc, Y.K.; Jeonga, T.S.; Lee, W.S. Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon. Bioorg. Med. Chem. Lett., 2007, 17, 1112-1116.
20. Calonghi, N.; Pagnotta, E.; Parolin, C.; Mangano, C.; Bolognesi, M.L.; Melchiorre, C.; Masotti, L. A new EGFR inhibitor induces apoptosis in colon cancer cells. Biochem. Biophys. Res. Commun., 2007, 354, 409-413.
21. Nishizawa, M.; Kohno, M.; Nishimura, M.; Kitagawa, A.; Niwano Y. Presence of peroxyradicals in cigarette smoke and the scavenging effect of shikonin, a naphthoquinone pigment. Chem. Pharm. Bull. (Tokyo), 2005, 53, 796-799.
22. a) Kundakovic, T.; Fokialakis, N.; Dobric, S.; Pratsinis, H.; Kletsas, D.; Kovacevic, N.; Chinou, I. Evaluation of the antiinflammatory and cytotoxic activities of naphthazarine derivatives from Onosma leptantha. Phytomedicine, 2006, 13, 290-4;
23. b). Tse, T.W. Use of common Chinese herbs in the treatment of psoriasis. Clin. Exp. Dermatol., 2003, 28, 469-475;
24. c) Singh, B.; Sharma, M.K.; Meghwal P.R.; Sahu, P.M.; Singh, S. Anti-inflammatory activity of shikonin derivatives from Arnebia hispidissima. Phytomedicine, 2003, 10, 375-380.
25. a) Couladouros, E.A.; Strongilos, A.T.; Papageorgiou, V.P.; Plyta, Z.F. A New efficient route for multigram asymmetric synthesis of Alkannin and Shikonin. Chem. Eur. J., 2002, 8, 1795-1803;
26. b) for alternative synthesis of compound 7. Polish J. Chem., 1982, 56, 411;
27. c) for alternative synthesis of compound 5: Bruce, J.M.; Creed, D.; Dawes, K. Light-induced and related reactions of quinones. Part VII. Cleavage and isomerisation of some (1- hydroxyalkyl)-1,4-benzoquinones. J. Chem. Soc. C, 1971, 2244-2252;
28. c) for alternative synthesis of compound 7a: Singh, R.; Khanna, J.M.; Anand, N. Synthesis and fungitoxicity of some substituted naphthoquinones and heteroarylquinones. Indian J. Chem. - Section B, 1989, 28, 490-493.
29. Maccarrone, M.; Ullrich, V. Redox regulation in disease and ageing. Cell Death Differ., 2004, 11, 949-951.
30. Kontogiorgis, C.A.; Hadjipavlou-Litina, D. Synthesis and antiinflammatory activity of coumarin derivatives. J. Med. Chem., 2005, 48, 6400-6408.
31. Pontiki, E.; Hadjipavlou-Litina, D. Synthesis of phenyl-substituted amides with antioxidant and anti-inflammatory activity as novel lipoxygenase inhibitors. Med. Chem., 2007, 3, 175-187.
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