Synthesis and evaluation of dithiolethiones as novel cyclooxygenase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 2, 2009, Pages 459-461

  Zanatta, Shannon D ^a,b   Manallack, David T ^c   Jarrott, Bevyn ^a,d   Williams, Spencer J ^b  

^a FLOREY INSTITUTE OF NEUROSCIENCE AND MENTAL HEALTH   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

^c MONASH UNIVERSITY   (Australia)

^d UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Cyclooxygenase; Dithiolethiones; Inhibitor; Modelling

Indexed keywords

3H 1,2 DITHIOLE 3 THIONE DERIVATIVE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; FLURBIPROFEN; INDOMETACIN; PHENOL; PROSTAGLANDIN SYNTHASE INHIBITOR; ROFECOXIB; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; IC 50; MOLECULAR DOCKING; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION;

CATALYTIC DOMAIN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; DRUG EVALUATION, PRECLINICAL; HYDROGEN BONDING; MODELS, MOLECULAR; THIONES;

EID: 57749096096     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.11.045     Document Type: Article

References (17)

1. Wallace J. Trends Pharmacol. Sci. 28 (2007) 501
2. Wilms H., Zecca L., Rosenstiel P., Sievers J., Deuschl G., and Lucius R. Curr. Pharm. Des. 13 (2007) 1925
3. Radi Z.A., and Khan N.K. Exp. Toxicol. Pathol. 58 (2006) 163
4. Tacconelli M.L., Capone M.L., and Patrignani P. Curr. Pharm. Des. 10 (2004) 589
5. Mason R.P., Walter M.F., McNulty H.P., Lockwood S.F., Byun J., Day C.A., and Jacob R.F. J. Cardiovasc. Pharmacol. 47 (2006) S7
6. Moreau A., Rao P.N.P., and Knaus E.E. Bioorg. Med. Chem. 14 (2006) 5340
7. Li L., Rossoni G., Sparatore A., Lee L.-C., Del Soldato P., and Moore P.K. Free Radic. Biol. Med. 42 (2007) 706
8. Nishinaga A., Shimizu T., Yasushi T., Matsuura T., and Hirotsu K. J. Org. Chem. 47 (1982) 2278
9. Berliner M.A., and Belecki K. J. Org. Chem. 70 (2005) 9618
10. Mordant E., de Andrade C., Touati R., Ratovelomanana-Vidal V., and Ben Hassine E.G.J.-P. Synthesis (2003) 2405
11. Curphey T.J. Tetrahedron Lett. 41 (2000) 9963
12. 3, requires C, 60.31; H, 6.55%.
13. 3, requires C, 61.32; H, 6.86; S, 27.28%.
14. 2 formed was quantitated using an ELISA assay.
15. Friesner R.A., Banks J.L., Murphy R.B., Halgren T.A., Klicic J.J., Mainz D.T., Repasky M.P., Knoll E.H., Shelley M., Perry J.K., Shaw D.E., Francis P., and Shenkin P.S. J. Med. Chem. 47 (2004) 1739
16. Halgren T.A., Murphy R.B., Friesner R.A., Beard H.S., Frye L.L., Pollard W.T., and Banks J.L. J. Med. Chem. 47 (2004) 1750
17. Schrödinger, LLC, Portland, Oregon, USA.