Synthesis of new 4-phenylpyrimidine-2(1H)-thiones and their potency to inhibit COX-1 and COX-2

European Journal of Medicinal Chemistry

Volumn 101, Issue , 2015, Pages 552-559

  Seebacher, Werner ^a   Faist, Johanna ^a   Presser, Armin ^a   Weis, Robert ^a   Saf, Robert ^b   Kaserer, Teresa ^c   Temml, Veronika ^c   Schuster, Daniela ^c   Ortmann, Sabine ^a   Otto, Nadine ^a   Bauer, Rudolf ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^c UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

4 Phenylpyrimidine 2(1H) thiones; Inhibition of cyclooxygenases

Indexed keywords

4 PHENYLPYRIMIDINE 2(1H) THIONE DERIVATIVE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DEXAMETHASONE; INDOMETACIN; N (2 CYCLOHEXYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; PROSTAGLANDIN SYNTHASE INHIBITOR; PYRIMIDINE DERIVATIVE; QUERCETIN; UNCLASSIFIED DRUG; THIOKETONE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; NONHUMAN; PHARMACOPHORE; PHYSICAL CHEMISTRY; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HUMAN; METABOLISM; SYNTHESIS;

CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; THIONES;

EID: 84937212798     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.07.003     Document Type: Article

References (38)

1. S.A. Said, A. El-G, E. Amr, N.M. Sabry, and M.M. Abdalla Analgesic, anticonvulsant and ant-inflammatory activities of some synthesized benzodiazepine, triazolopyrimidine and bis-imide derivatives Eur. J. Med. Chem. 44 2009 4787 4792
2. A.-M.A. Sammour, M.M. El-Deen, and A.-el-H.M. Nonr Condensation of unsaturated ketones with thioureas U.A.R. J. Chem. 13 1970 7 24
3. G. Zigeuner, H. Brunetti, H. Ziegler, and M. Bayer Dihydro-6-methyl-(or -6-styryl-)-4-phenyl-2(1H)-pyrimidinones (-thiones); Hexahydro-5-benzoyl- (or -cinnamoyl-)-4,7-diphenyl-2(1H)-quinazolinones (-thiones) Chem. Mon. 101 1970 1767 1787
4. Y. Tamura Nonsteroidal antiinflammatory agents. 1. 5-Alkoxy-3-biphenylylacetic acids and related compounds as new potential antiinflammatory agents J. Med. Chem. 20 1977 709 714
5. T. Nishimura Antituberculous compounds. II. Thiosemicarbazones from Benzalacetones Bull. Chem. Soc. Jpn. 26 1953 253 254
6. H.O. Kalinowski, S. Berger, and S. Braun 13C-NMR-Spektroskopie 1984 Georg Thieme Verlag Stuttgart, New York
7. B.L. Fiebich, M. Grozdeva, S. Hess, M. Hüll, U. Danesch, A. Bodensieck, and R. Bauer Petasites hybridus extracts in vitro inhibit COX-2 and PGE2 release by direct interaction with the enzyme and by preventing microglial cells Planta Med. 71 2005 12 19
8. E.A. Reiniger, and R. Bauer Prostaglandin-H-synthase (PGHS)-1 and -2 microtiter assays for testing of herbal drugs and in vitro inhibition of PGHS-isoenzyms by polyunsaturated fatty acids from Platycodi radix Phytomedicine 13 2006 164 169
9. K.J. Livak, and T.D. Schmittgen Analysis of relative gene expression data using real-time quantitative PCR and the 2-ΔΔCT Method Methods 25 2001 402 408
10. C.G. Wermuth, C.R. Ganellin, P. Lindberg, and L.A. Mitscher Glossary of terms used in medicinal chemistry (IUPAC recommendations 1998) Pure Appl. Chem. 70 1998 1129 1143
11. G. Wolber, and T. Langer LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters J. Chem. Inf. Model 45 2005 160 169
12. H. Berman, J. Westbrook, Z. Feng, G. Gilliland, T. Bhat, H. Weissig, I. Shindyalov, and P. Bourne The protein data bank Nucleic Acids Res. 28 2000 235 242
13. P.C.D. Hawkins, A.G. Skillman, G.L. Warren, B.A. Ellingson, and M.T. Stahl Conformer generation with OMEGA: algorithm and validation using high quality structures from the Protein Databank and Cambridge Structural Database J. Chem. Inf. Model 50 2010 572 584
14. P.C.D. Hawkins, and A. Nicholls Conformer generation with OMEGA: learning from the data set and the analysis of failures J. Chem. Inf. Model 52 2012 2919 2936
15. G. Wolber, A.A. Dornhofer, and T. Langer Efficient overlay of small organic molecules using 3D pharmacophores J. Comput. Aided Mol. Des. 20 2006 773 788
16. D.B. Kitchen, H. Decornez, J.R. Furr, and J. Bajorath Docking and scoring in virtual screening for drug discovery: methods and applications Nat. Rev. Drug Discov. 3 2004 935 949
17. V. Temml, T. Kaserer, Z. Kutil, P. Landa, T. Vanek, and D. Schuster Pharmacophore Modeling for Cyclooxygenase-1 and 2 inhibitors with LigandScout in comparison to Discovery Studio Fut. Med. Chem. 6 2014 1869 1881
18. H. van de Waterbeemd, and E. Gifford ADMET in silico modeling: towards prediction paradise? Nat. Rev. Drug Discov. 2 3 2003 192 204
19. M.S. Lajiness, M. Vieth, and J. Erickson Molecular properties that influence oral drug-like behavior Curr. Opin. Drug Discov. Dev. 7 4 2004 470 477
20. M.C. Wenlock, R.P. Austin, P. Barton, A.M. Davis, and P.D. Leeson A comparison of Physiochemical Property Profiles of development and Marketed oral drugs J. Med. Chem. 46 7 2003 1250 1256
21. J.D. Hughes, J. Blagg, D.A. Price, S. Bailey, G.A. DeCrescenzo, R.V. Devraj, E. Ellsworth, Y.M. Fobian, M.E. Gibbs, R.W. Gilles, N. Greene, E. Huang, T. Krieger-Burke, J. Loesel, T. Wager, L. Whiteley, and Y. Zhang Physiochemical drug properties associated with in vivo toxicological outcomes Bioorg. Med. Chem. Lett. 18 17 2008 4872 4875
22. C.A. Lipinski, and A. Hopkins Navigating chemical space for biology and medicine Nat. (London, U. K.) 432 7019 2004 855 861
23. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Deliv. Rev. 23 1-3 1997 3 25
24. C.A. Lipinski Lead- and drug-like compounds: the rule-of-five revolution Drug Discov. Today: Technol. 1 4 2004 337 341
25. D.F. Veber, S.R. Johnson, H.-Y. Cheng, B.R. Smith, K.W. Ward, and K.D. Kopple Molecular properties that influence the oral bioavailability of drug candidates J. Med. Chem. 45 12 2002 2615 2623
26. A.K. Ghose, V.N. Viswanadhan, and J.J. Wendoloski A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases J. Comb. Chem. 1 1 1999 55 68
27. H. Pajouhesh, and G.R. Lenz Medicinal chemical properties of successful central nervous system drugs NeuroRx 2 4 2005 541 553
28. H. van de Waterbeemd Physicochemical approaches to drug absorption R. Mannhold, H. Kubinyi, G. Folkers, H. van de Waterbeemd, B. Testa, (Eds.) Drug Bioavailability 2008 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim, Germany 69 99
29. K.J. Box, and J. Comer Using measured pKa, LogP and solubility to investigate supersaturation and predict BCS class Curr. Drug Metab. 9 9 2008 869 878
30. A. Dahan, O. Wolk, Y.H. Kim, C. Ramachandran, G.M. Crippen, T. Takagi, M. Bermejo, and G.L. Amidon Purely in silico BCS classification: science based quality standards for the world's drugs Mol. Pharm. 10 11 2013 4378 4390
31. G.L. Amidon, H. Lennernaes, V.P. Shah, and J.R. Crison A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability Pharm. Res. 12 3 1995 413 420
32. A. Dahan, J.M. Miller, and G.L. Amidon Prediction of solubility and permeability class membership: provisional BCS classification of the world's top oral drugs AAPS J. 11 4 2009 740 746
33. G.L. Amidon, H. Lennernas, V.P. Shah, and J.R. Crison A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability, Pharm Res 12, 413-420, 1995-Backstory of BCS AAPS J. 16 5 2014 894 898
34. G.R. Bickerton, G.V. Paolini, J. Besnard, S. Muresan, and A.L. Hopkins Quantifying the chemical beauty of drugs Nat. Chem. 4 2 2012 90 98
35. M.P. Gleeson, A. Hersey, D. Montanari, and J. Overington Probing the links between in vitro potency, ADMET and physicochemical parameters Nat. Rev. Drug Discov. 10 3 2011 197 208
36. R.G. Kurumbail, A.M. Stevens, J.K. Gierse, J.J. McDonald, R.A. Stegeman, J.Y. Pak, D. Gildehaus, J.M. Miyashiro, T.D. Penning, and K. Seibert Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents Nature 384 1996 664-648
37. B.S. Selinsky, K. Gupta, C.T. Sharkey, and P.J. Loll Structural analysis of NSAID binding by protaglandine H2 synthase: time-dependent and time-independent inhibitors elicit identical enzyme conformations Biochemistry 40 2001 5172 5180
38. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 267 1997 727 748