Discovery of pyridine-2-ones as novel class of multidrug resistance (MDR) modulators: First structure-activity relationships

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 21, 2011, Pages 6309-6315

  Krawczyk, Sören ^a   Otto, Monika ^a   Otto, Alexander ^a   Coburger, Claudius ^a   Krug, Martin ^a   Seifert, Marianne ^a   Tell, Volkmar ^a   Molnár, Joséf ^b   Higeroth, Andreas ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Efflux pump inhibition; Lead structure; Multidrug resistance (MDR); P glycoprotein (P gp); Structure activity relationships (SAR)

Indexed keywords

1 BENZYL 3 CYANO 2 OXO 1,2 DIHYDROPYRIDINE; 1 BENZYL 3 CYANO 4 (2 METHYLPHENYL) 2 OXO 1,2,3,4 TETRAHYDROPYRIDINE; 1 BENZYL 3 CYANO 4 (4 METHYLPHENYL) 2 OXO 1,2,3,4 TETRAHYDROPYRIDINE; 1 BENZYL 3 CYANO 4 PHENYL 2 OXO 1,2 DIHYDROPYRIDINE; 1 BENZYL 3 CYANO 4 PHENYL 2 OXO 1,2,3,4 TETRAHYDRONICOTINATE; 1,4 DIBENZYL 3 CYANO 2 OXO 1,2 DIHYDROPYRIDINE; 1,4 DIBENZYL 3 CYANO 2 OXO 1,2,3,4 TETRAHYDROPYRIDINE; 3 CYANO 2 METHOXYPYRIDINE; ANTINEOPLASTIC AGENT; BENZYL 1 BENZYL 2 OXO 1,2 DIHYDRONICOTINATE; BENZYL 1 BENZYL 2 OXO 4 PHENYL 1,2,3,4 TETRAHYDRONICOTINATE; CYCLOSPORIN A; DAUNORUBICIN; GLYCOPROTEIN P; METHYL 1 BENZYL 2 OXO 1,2 DIHYDRONICOTINATE; METHYL 1 BENZYL 2 OXO 4 (2 METHYLPHENYL) 1,2 DIHYDRONICOTINATE; METHYL 1 BENZYL 2 OXO 4 (2 METHYLPHENYL) 1,2,3,4 TETRAHYDRONICOTINATE; METHYL 1 BENZYL 2 OXO 4 (4 METHOXYLPHENYL) 1,2 DIHYDRONICOTINATE; METHYL 1 BENZYL 2 OXO 4 (4 METHOXYPHENYL) 1,2,3,4 TETRAHYDRONICOTINATE; METHYL 1 BENZYL 2 OXO 4 (4 METHYLPHENYL) 1,2 DIHYDRONICOTINATE; METHYL 1 BENZYL 2 OXO 4 (4 METHYLPHENYL) 1,2,3,4 TETRAHYDRONICOTINATE; METHYL 1 BENZYL 2 OXO 4 PHENYL 1,2 DIHYDRONICOTINATE; METHYL 1 BENZYL 2 OXO 4 PHENYL 1,2,3,4 TETRAHYDRONICOTINATE; METHYL 1,4 DIBENZYL 2 OXO 1,2,3,4 TETRAHYDRONICOTINATE; METHYL 1,4 DIBENZYL 2 OXO 4 PHENYL 1,2 DIHYDRONICOTINATE; METHYL 2 METHOXYNICOTINATE; PYRIDINE 2 ONE DERIVATIVE; RITONAVIR; UNCLASSIFIED DRUG; UNINDEXED DRUG; VERAPAMIL;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; FACILE SYNTHESIS; HYDROGEN BOND; MULTIDRUG RESISTANCE; NONHUMAN; PROTEIN STRUCTURE; PROTEIN TARGETING; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 80054961171     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.09.005     Document Type: Article

References (39)

1. Gottesman, M. M.; Ling, V. FEBS Lett. 2006, 580, 998.
2. Lage, H. Cell Mol. Life Sci. 2008, 65, 3145.
3. Eckford, P. D. W.; Sharom, F. J. Chem. Rev. 2009, 109, 2989.
4. Gillet, J.-P.; Efferth, T.; Remacle, J. Biochim. Biophys. Acta 2007, 1775, 237.
5. Dean, M.; Rzhetsky, A.; Allikmets, R. Genome Res. 2009, 11, 1156.
6. Baumert, C.; Hilgeroth, A. Anti-Cancer Agents Med. Chem. 2009, 9, 415.
7. Wang, R. B.; Kuo, C. L.; Lien, L. L.; Lien, E. J. J. Clin. Pharm. Ther. 2003, 28, 203.
8. Chang, C.; Bahadduri, P. M.; Polli, J. E.; Swaan, P. W.; Ekins, S. Drug Metab. Disp. 2006, 34, 1976.
9. Mahon, F. X.; Belloc, F.; Lagarde, V.; Chollet, C.; Moreau-Gaudry, F.; Reiffers, J.; Goldman, J. M.; Melo, J. V. Blood 2003, 101, 2368.
10. Matsui, H.; Takeshita, A.; Naito, K.; Shinjo, K.; Shigeno, K.; Maekawa, M.; Yamakaw, Y.; Tanimito, M.; Kobayashi, M.; Ohnishi, K.; Ohno, R. Leukemia 2002, 16, 813.
11. Bonavida, B. Oncogene 2007, 26, 3629.
12. Krühn, A.; Wang, A.; Fruehauf, J. H.; Lage, H. Cell Cycle 2009, 20, 3349.
13. Avendanó, C.; Menéndez, J. C. Med. Chem. Rev.-Online 2004, 1, 419.
14. Choi, C.-H. Cancer Cell Int. 2005, 5, 30.
15. Tain, Q.; Zhang, J.; Chan, E.; Duan, W.; Zhou, S. Drug Dev. Res. 2005, 64, 1.
16. Sheps, J. A.; Ling, V. Eur. J. Physiol. 2007, 453, 545.
17. Krishna, R.; Mayer, L. D. Eur. J. Pharm. Sci. 2000, 11, 265.
18. Kawase, M.; Motohashi, N. Curr. Drug Targets 2003, 4, 31.
19. Lage, H.; Duarte, N.; Coburger, C.; Hilgeroth, A.; Ferreira, M. J. U. Phytomedicine 2010, 17, 441.
20. Tanabe, H.; Tasaka, S.; Ohmori, H.; Gomi, N.; Sasaki, Y.; Machida, T.; Iino, M.; Kiue, A.; Naito, S.; Kuwano, M. Bioorg. Med. Chem. 1998, 6, 2219.
21. Tsuruo, T.; Iida, H.; Tukagoshi, S.; Sakurai, Y. Cancer Res. 1981, 41, 1967.
22. Kawase, M.; Shah, A.; Gaveriya, H.; Motohashi, N.; Sakagami, H.; Varga, A.; Molnár, J. Bioorg. Med. Chem. 2002, 10, 1051.
23. Shah, A.; Gaveriya, H.; Motohashi, N.; Kawase, M.; Saito, S.; Sakagami, H.; Satoh, K.; Tada, Y.; Solymosi, A.; Walfard, K.; Molnár, J. Anticancer Res. 2000, 20, 373.
24. Seelig, A.; Landwojtowicz, E. Eur. J. Pharm. Sci. 2000, 12, 31.
25. Ecker, G.; Huber, M.; Schmidt, D.; Chiba, P. Mol. Pharmacol. 1999, 56, 791.
26. Hilgeroth, A.; Molnár, J.; De Clercq, E. Angew. Chem. 2002, 114, 3772. Angew. Chem. Int. Ed. 2002, 41, 3623.
27. Seelig, A.; Blatter, L.; Wohnsland, F. Int. J. Clin. Pharmacol. Ther. 2000, 38, 111.
28. Hilgeroth, A.; Brachwitz, K.; Baumeister, U. Heterocycles 2001, 55, 661.
29. Commins, D. L.; Stroud, E. D.; Herrick, J. J. Heterocycles 1984, 22, 151.
30. Hilgeroth, A.; Baumeister, U. Angew. Chem. 2000, 112, 588. Angew. Chem. Int. Ed. 2000, 39, 576.
31. Hiroya, K.; Kawamoto, K.; Sakamoto, T. Synlett 2006, 16, 2636.
32. Kuckländer, U.; Hilgeroth, A. Arch. Pharm. 1994, 327, 287.
33. Coburger, C.; Lage, H.; Molnár, J.; Hilgeroth, A. Pharm. Res. 2008, 26, 182.
34. Munic, V.; Kelneric, Z.; Mikac, L.; Haber, V. E. Eur. J. Pharm. Sci. 2010, 41, 86.
35. Lee, S. L.; Alexander, R. S.; Smallwood, A.; Trievel, R.; Mersinger, L.; Weber, P. C.; Kettner, C. Biochemistry 1997, 36, 13180.
36. Coburger, C.; Lage, H.; Molnár, J.; Langner, A.; Hilgeroth, A. J. Pharm. Pharmacol. 2010, 62, 1704.
37. Coburger, C.; Wollmann, J.; Krug, M.; Baumert, C.; Seifert, M.; Molnár, J.; Lage, H.; Hilgeroth, A. Bioorg. Med. Chem. 2010, 18, 4983.
38. Weaver, J. L.; Szabo, D.; Pine, P. S.; Gottesmann, S.; Goldberg, A.; Aszalos, A. Int. J. Cancer 1993, 54, 456.
39. Cornwell, M. M.; Pastan, I.; Gottesmann, M. M. J. Biol. Chem. 1987, 262, 2166.