Design, synthesis, and DNA-binding of N-alkyl(anilino)quinazoline derivatives

Journal of Medicinal Chemistry

Volumn 53, Issue 22, 2010, Pages 8089-8103

  Garofalo, Antonio ^a,b   Goossens, Laurence ^a,b   Baldeyrou, Brigitte ^a,c,d   Lemoine, Amélie ^a,b   Ravez, Séverine ^a,b   Six, Perrine ^a,b   David Cordonnier, Marie Hélène ^a,c   Bonte, Jean Paul ^a,b   Depreux, Patrick ^a,b   Lansiaux, Amélie ^a,c,d   Goossens, Jean François ^a,e  

^a UNIV LILLE   (France)

^b Faculté des Sciences Pharmaceutiques et Biologiques Université de Lille   (France)

^c JEAN PIERRE AUBERT RESEARCH CENTER   (France)

^d CENTRE OSCAR LAMBRET   (France)

^e Université de Lille 1 Sciences et Technologies   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 (2,5 DIBROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (3 BROMO 4 METHYLANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (3 CHLORO 4 FLUOROPHENOXY) 6,7 DIMETHOXYQUINAZOLINE; 4 (3 CHLORO 4 METHYLANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (3 FLUORO 4 METHYLANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (3 NITROANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (3 TRIFLUOROMETHYL 4 METHYLANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (4 BROMO 2 FLUOROANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (4 BROMO 2 FLUOROPHENOXY) 6,7 DIMETHOXYQUINAZOLINE; 4 (4 TRIFLUOROMETHYLANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 2,5 DIBROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 3 AMINOANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 3 BROMO 4 METHYLANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 3 CHLORO 4 FLUOROANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 3 CHLORO 4 METHYLANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 3 FLUORO 4 METHYLANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 3 FLUOROANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 3 NITROANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 3 TRIFLUOROMETHYL 4 METHYLANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 4 AMINOANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 4 BROMO 2 FLUOROANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 4 BROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 4 NITROANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (N METHYL 4 TRIFLUOROMETHYLANILINO) 6,7 DIMETHOXYQUINAZOLINE; ANTINEOPLASTIC AGENT; INTERCALATING AGENT; N [4 [N METHYL 6,7 DIMETHOXYQUINAZOLIN 4 YLAMINO]PHENYL] N' PHENYLUREA; N BUTYL N' [4 [N METHYL 6,7 DIMETHOXYQUINAZOLIN 4 YLAMINO]PHENYL]UREA; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CYTOTOXICITY; DRUG DESIGN; DRUG DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; PHARMACOPHORE; SUBSTITUTION REACTION;

ANILINE COMPOUNDS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CIRCULAR DICHROISM; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; FLUORESCENCE; HUMANS; INTERCALATING AGENTS; NUCLEIC ACID CONFORMATION; QUINAZOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; TOPOISOMERASE I INHIBITORS; TRANSITION TEMPERATURE;

EID: 78649505476     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1009605     Document Type: Article

References (26)

1. Traxler, P.; Bold, G.; Buchdunger, E.; Caravatti, G.; Furet, P.; Manley, P.; O'Reilly, T.; Wood, J.; Zimmermann, J. Tyrosine kinase inhibitors: from rational design to clinical trials Med. Res. Rev. 2001, 21, 499-512
2. Denny, W. A. The 4-anilinoquinazoline class of inhibitors of erbB family of receptor tyrosine kinase Farmaco 2001, 56, 51-56
3. Ranson, M.; Wardell, S. Gefitinib, a novel, orally administrated agent for the treatment of cancer J. Clin. Pharm. Ther. 2004, 29, 95-103
4. Nelson, M. H.; Dolder, C. R. Lapatinib: a novel dual tyrosine kinase inhibitor with activity in solid tumors Ann. Pharmacother. 2006, 40, 261-269
5. Gourdie, T. A.; Valu, K. K.; Gravatt, G. L.; Boritzki, T. J.; Baguley, B. C.; Wakelin, L. P. G.; Wilson, W. R.; Woodgate, P. D.; Denny, W. A. DNA-directed alkylating agents. 1. Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the reactivity of the mustard J. Med. Chem. 1990, 33, 117-1186
6. Prakash, A. S.; Denny, W. A.; Gourdie, T. A.; Valu, K. K.; Woodgate, P. D.; Wakelin, L. P. G. DNA-directed alkylating ligands as potential antitumor agents: sequence specificity of alkylation by intercalating aniline mustards Biochemistry 1990, 29, 9799-9807
7. Ryckebusch, A.; Garcin, D.; Lansiaux, A.; Goossens, J. F.; Baldeyrou, B.; Houssin, R.; Bailly, C.; Hénichart, J. P. Synthesis, cytotoxicity, DNA interaction, and topoisomerase II inhibition properties of novel indeno[2,1- c ]quinolin-7-one and indeno[1,2- c ]isoquinolin-5,11-dione derivatives J. Med. Chem. 2008, 51, 3617-3629
8. Chackal, S.; Facompré, M.; Houssin, R.; Goossens, J. F.; Pommery, N.; Hénichart, J. P.; Bailly, C. Highly cytotoxic benzo[ c ]pyrido[2,3,4- k, l ]acridines Bioorg. Med. Chem. Lett. 2003, 13, 943-946
9. Anthony, S.; Agama, K. K.; Miao, Z. H.; Hollingshead, M.; Holbeck, S. L.; Wright, M. H.; Varticovski, L.; Nagarajan, M.; Morrell, A.; Cushman, M.; Pommier, Y. Bisindenoisoquinoline bis-1,3-{(5,6-dihydro-5,11-diketo-11 H -indeno[1,2- c ]isoquinoline)-6-propylamino}propane bis(trifluoroacetate) (NSC 727357), a DNA intercalator and topoisomerase inhibitor with antitumor activity Mol. Pharmacol. 2006, 70, 1109-1120
10. Palchaudhuri, R.; Hergenrother, P. J. DNA as target for anticancer compounds: methods to determine the mode of binding and the mechanism of action Curr. Opin. Biotechnol. 2007, 18, 497-503
11. Bridges, A. J.; Cody, D. R.; Zhou, H.; McMichael, A.; Fry, D. W. Enantioselective inhibition of the epidermal growth factor receptor tyrosine kinase by 4-(α-phenethylamino)quinazolines Bioorg. Med. Chem. 1995, 3, 1651-1656
12. Goossens, J. F.; Bouey-Bencteux, E.; Houssin, R.; Hénichart, J. P.; Colson, P.; Houssier, C.; Laine, W.; Baldeyrou, B.; Bailly, C. DNA interaction of the tyrosine protein kinase inhibitor PD153035 and its N -methyl analogue Biochemistry 2001, 40, 4663-4671
13. Bridges, A. J.; Zhou, H.; Cody, D. R.; Rewcastle, G. W.; McMichael, A.; Hollis Showalter, H. D.; Fry, D. W.; Kraker, A. J.; Denny, W. A. Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor J. Med. Chem. 1996, 39, 267-276
14. Bouey-Bencteux, E.; Loison, C.; Pommery, N.; Houssin, R.; Hénichart, J. P. Synthesis and antiproliferative properties of 4-aminoquinazoline derivatives as inhibitors of EGF receptor-associated tyrosine kinase activity Anti-Cancer Drug Des. 1998, 13, 893-922
15. Furuta, T.; Sakai, T.; Senga, T.; Osawa, T.; Kubo, K.; Shimizu, T.; Suzuki, R.; Yoshino, T.; Endo, M.; Miwa, A. Identification of potent and selective inhibitors of PDGF receptor autophosphorylation J. Med. Chem. 2006, 49, 2186-2192
16. Matsuno, K.; Ushiki, J.; Seishi, T.; Ichimura, M.; Giese, N. A.; Yu, J. C.; Takahashi, S.; Oda, S.; Nomoto, Y. Potent and selective inhibitors of platelet-derived growth factor receptor phosphorylation. 3. Replacement of quinazoline moiety and improvement of metabolic polymorphism of 4-[4-(N -substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives J. Med. Chem. 2003, 46, 4910-4925 (Pubitemid 37352031)
17. Nordén, B.; Tjerneld, F. Structure of methylene blue-DNA complexes studied by linear and circular dichroism spectroscopy Biopolymers. 1982, 21, 1713-1734
18. Facompré, M.; Carrasco, C.; Colson, P.; Houssier, C.; Chisholm, J. D.; Van Vranken, D. L.; Bailly, C. DNA binding and topoisomerase I poisoning activities of novel disaccharide indolocarbazoles Mol. Pharmacol. 2002, 62, 1215-27
19. Bailly, C.; Waring, M. J. Comparison of different footprinting methodologies for detecting binding sites for a small ligand on DNA J. Biomol. Struct. Dyn. 1995, 12, 869-898
20. VanBrocklin, H. F.; Lim, J. K.; Coffing, S. L.; Hom, D. L.; Negash, K.; Ono, M. Y.; Gilmore, J. L.; Bryant, I.; Riese, D. J. Anilinodialkoxyquinazolines: screening epidermal growth factor receptor tyrosine kinase inhibitors for potential tumor imaging probes J. Med. Chem. 2005, 48, 7445-7456
21. Bridges, A. J.; Zhou, H.; Cody, D. R.; Rewcastle, G. W.; McMichael, A.; Showalter, H. D.; Fry, D. W.; Kraker, A. J.; Denny, W. A. Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor J. Med. Chem. 1996, 39, 267-276
22. Rocco, S. A.; Barbarini, E.; Rittner, R. Synthesis 2004, 3, 429-435
23. Gibson, K. H.; Grundy, W.; Godfrey, A.; Woodburn, J. R.; Ashton, S. E.; Curry, B. J.; Scarlett, L.; Barker, A. J.; Brown, D. S. Epidermal growth factor receptor tyrosine kinase: Structure-activity relationships and antitumour activity of novel quinazolines Bioorg. Med. Chem. Lett. 1997, 7, 2723-2728
24. Myers, M. R.; Setzer, N. N.; Spada, A. P.; Persons, P. E.; Ly, C. Q.; Maguire, M. P.; Zulli, A. L.; Cheney, D. L.; Zilberstein, A.; Johnson, S. E.; Franks, C. E.; Mitchell, K. J. The synthesis and SAR of new 4-(N -alkyl- N -phenyl)amino-6,7-dimethoxyquinazolines and 4-(N -alkyl- N -phenyl) aminopyrazolo[3,4- d ]pyrimidines, inhibitors of CSF-1R tyrosine kinase activity Bioorg. Med. Chem. Lett. 1997, 7, 421-424
25. Kubo, K.; Shimizu, T.; Ohyama, S.; Murooka, H.; Nishitoba, T.; Kato, S.; Kobayashi, Y.; Yagi, M.; Isoe, T.; Nakamura, K.; Osawa, T.; Izawa, T. A novel series of 4-phenoxyquinolines: potent and highly selective inhibitors of PDGF receptor autophosphorylation Bioorg. Med. Chem. Lett. 1997, 7, 2935-2940
26. Bailly, C.; Kluza, J.; Martin, C.; Ellis, T.; Waring, M. J. DNase I footprinting of small molecule binding sites on DNA Methods Mol. Biol. 2005, 288, 319-342