A class of 5-benzylidene-2-phenylthiazolinones with high potency as direct 5-lipoxygenase inhibitors

Journal of Medicinal Chemistry

Volumn 54, Issue 6, 2011, Pages 1943-1947

  Hofmann, Bettina ^a   Barzen, Sebastian ^a   Rödl, Carmen B ^a   Kiehl, Andreas ^a   Borig, Julia ^a   Živkovi , Aleksandra ^a   Stark, Holger ^a   Schneider, Gisbert ^a,b   Steinhilber, Dieter ^a  

^a GOETHE UNIVERSITY   (Germany)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 CHLOROPHENYL) 5 (4 METHOXYBENZYLIDENE) 5H THIAZOL ONE; 5 BENZYLIDENE 2 PHENYL 5H THIAZOL ONE; 5 BENZYLIDENE 2 PHENYLTHIAZOLINONE; ARACHIDONATE 5 LIPOXYGENASE; LIPOXYGENASE INHIBITOR; N [3 (3 PHENOXYPHENYL)ALLYL]ACETOHYDROXAMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CELL FREE SYSTEM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; NEUTROPHIL;

ARACHIDONATE 5-LIPOXYGENASE; BENZYLIDENE COMPOUNDS; LIPOXYGENASE INHIBITORS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 79952800679     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101165z     Document Type: Article

References (25)

1. Peters-Golden, M.; Henderson, W. R., Jr. Leukotrienes N. Engl. J. Med. 2007, 357, 1841-1854
2. Werz, O.; Steinhilber, D. Therapeutic options for 5-lipoxygenase inhibitors Pharmacol. Ther. 2006, 112, 701-718 (Pubitemid 44592614)
3. R̂dmark, O.; Werz, O.; Steinhilber, D.; Samuelsson, B. 5-Lipoxygenase: regulation of expression and enzyme activity Trends Biochem. Sci. 2007, 32, 332-341 (Pubitemid 47021417)
4. Raydmark, O.; Samuelsson, B. Microsomal prostaglandin E synthase-1 and 5-lipoxygenase: potential drug targets in cancer J. Intern. Med. 2010, 268, 5-14
5. Chen, Y.; Hu, Y.; Zhang, H.; Peng, C.; Li, S. Loss of the Alox5 gene impairs leukemia stem cells and prevents chronic myeloid leukemia Nat. Genet. 2009, 41, 783-792
6. Shumilina, E.; Kiedaisch, V.; Akkel, A.; Lang, P.; Hermle, T.; Kempe, D.; Huber, S. M.; Wieder, T.; Laufer, S.; Lang, F. Stimulation of suicidal erythrocyte death by lipoxygenase inhibitor Bay-Y5884 Cell. Physiol. Biochem. 2006, 18, 233-242 (Pubitemid 44946978)
7. Lang, P.; Kasinathan, R.; Brand, V.; Duranton, C.; Lang, C.; Koka, S.; Shumilina, E.; Kempe, D.; Tanneur, V.; Akel, A.; Lang, K.; Foller, M.; Kun, J. F.; Kremsner, P.; Wesselborg, S.; Laufer, S.; Clemen, C.; Herr, C.; Noegel, A.; Wieder, T.; Gulbins, E.; Lang, F.; Huber, S. Accelerated clearance of Plasmodium-infected erythrocytes in sickle cell trait and annexin-A7 deficiency Cell. Physiol. Biochem. 2009, 24, 415-428
8. Menna, C.; Olivieri, F.; Catalano, A.; Procopio, A. Lipoxygenase inhibitors for cancer prevention: promises and risks Curr. Pharm. Des. 2010, 16, 725-733
9. Hofmann, B.; Franke, L.; Proschak, E.; Tanrikulu, Y.; Schneider, P.; Steinhilber, D.; Schneider, G. Scaffold-hopping cascade yields potent inhibitors of 5-lipoxygenase ChemMedChem 2008, 3, 1535-1538
10. Franke, L.; Schwarz, O.; Muller-Kuhrt, L.; Hoernig, C.; Fischer, L.; George, S.; Tanrikulu, Y.; Schneider, P.; Werz, O.; Steinhilber, D.; Schneider, G. Identification of natural-product-derived inhibitors of 5-lipoxygenase activity by ligand-based virtual screening J. Med. Chem. 2007, 50, 2640-2646 (Pubitemid 46896071)
11. Bauknecht, H.; Zell, A.; Bayer, H.; Levi, P.; Wagener, M.; Sadowski, J.; Gasteiger, J. Locating biologically active compounds in medium-sized heterogeneous datasets by topological autocorrelation vectors: dopamine and benzodiazepine agonists J. Chem. Inf. Comput. Sci. 1996, 36, 1205-1213 (Pubitemid 126581788)
12. Selzer, P.; Ertl, P. Identification and classification of GPCR ligands using self-organizing neural networks QSAR Comb. Sci. 2005, 24, 270-276 (Pubitemid 40524381)
13. Unangst, P. C.; Connor, D. T.; Cetenko, W. A.; Sorenson, R. J.; Kostlan, C. R.; Sircar, J. C.; Wright, C. D.; Schrier, D. J.; Dyer, R. D. Synthesis and biological evaluation of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl] methylene]oxazoles, -thiazoles, and -imidazoles: novel dual 5-lipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity J. Med. Chem. 1994, 37, 322-328 (Pubitemid 24063052)
14. Geronikaki, A. A.; Lagunin, A. A.; Hadjipavlou-Litina, D. I.; Eleftheriou, P. T.; Filimonov, D. A.; Poroikov, V. V.; Alam, I.; Saxena, A. K. Computer-aided discovery of anti-inflammatory thiazolidinones with dual cyclooxygenase/lipoxygenase inhibition J. Med. Chem. 2008, 51, 1601-1609 (Pubitemid 351438844)
15. Werz, O. Inhibition of 5-lipoxygenase product synthesis by natural compounds of plant origin Planta Med. 2007, 73, 1331-1357 (Pubitemid 350084452)
16. Tateson, J. E.; Randall, R. W.; Reynolds, C. H.; Jackson, W. P.; Bhattacherjee, P.; Salmon, J. A.; Garland, L. G. Selective inhibition of arachidonate 5-lipoxygenase by novel acetohydroxamic acids: biochemical assessment in vitro and ex vivo Br. J. Pharmacol. 1988, 94, 528-539
17. Willett, P.; Barnard, J. M.; Downs, G. M. Chemical similarity searching J. Chem. Inf. Comput. Sci. 1998, 38, 983-996 (Pubitemid 128591261)
18. Durant, J. L.; Leland, B. A.; Henry, D. R.; Nourse, J. G. Reoptimization of MDL keys for use in drug discovery J. Chem. Inf. Comput. Sci. 2002, 42, 1273-1280 (Pubitemid 35468313)
19. Martin, Y. C.; Kofron, J. L.; Traphagen, L. M. Do structurally similar molecules have similar biological activity- J. Med. Chem. 2002, 45, 4350-4358 (Pubitemid 35025581)
20. Muchmore, S. W.; Debe, D. A.; Metz, J. T.; Brown, S. P.; Martin, Y. C.; Hajduk, P. J. Application of belief theory to similarity data fusion for use in analog searching and lead hopping J. Chem. Inf. Model. 2008, 48, 941-948
21. Zayed, E. M.; Elbannany, A. A. A.; Ghozlan, S. A. S. Studies on thiazolin-4-one: synthesis of some pyrano[2,3- b ]thiazole derivatives Pharmazie 1985, 40, 194-196 (Pubitemid 15124232)
22. Ford-Hutchinson, A. W.; Gresser, M.; Young, R. N. 5-Lipoxygenase Annu. Rev. Biochem. 1994, 63, 383-417 (Pubitemid 24218638)
23. Peltason, L.; Bajorath, J. SAR index: quantifying the nature of structure-activity relationships J. Med. Chem. 2007, 50, 5571-5578 (Pubitemid 350106013)
24. Wawer, M.; Peltason, L.; Weskamp, N.; Teckentrup, A.; Bajorath, J. Structure-activity relationship anatomy by network-like similarity graphs and local structure-activity relationship indices J. Med. Chem. 2008, 51, 6075-6084
25. Werz, O.; Bürkert, E.; Samuelsson, B.; Rdmark, O.; Steinhilber, D. Activation of 5-lipoxygenase by cell stress is calcium independent in human polymorphonuclear leukocytes Blood 2002, 99, 1044-1052 (Pubitemid 34527142)