A new synthetic route to original sulfonamide derivatives in 2-trichloromethylquinazoline series: A structure-activity relationship study of antiplasmodial activity

Molecules

Volumn 17, Issue 7, 2012, Pages 8105-8117

  Primas, Nicolas ^a   Verhaeghe, Pierre ^a   Cohen, Anita ^a,b   Kieffer, Charline ^a   Dumètre, Aurélien ^b   Hutter, Sébastien ^b   Rault, Sylvain ^c   Rathelot, Pascal ^a   Azas, Nadine ^b   Vanelle, Patrice ^a  

^a AIX MARSEILLE UNIV   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

^c CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

Author keywords

Antiplasmodial activity; Microwaves; Quinazoline; Sulfonamide; Trichloromethyl group

Indexed keywords

ANTIMALARIAL AGENT; QUINAZOLINE DERIVATIVE; SULFONAMIDE;

ARTICLE; CELL DEATH; CELL STRAIN HEPG2; CHEMISTRY; DRUG EFFECT; HUMAN; IC 50; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTIMALARIALS; CELL DEATH; HEP G2 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; PLASMODIUM FALCIPARUM; QUINAZOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84864591393     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17078105     Document Type: Article

References (29)

1. Fry, D.W.; Kraker, A.J.; McMichael, A.; Ambroso, L.A.; Nelson, J.M.; Leopold, W.R.; Connors, R.W.; Bridges, A.J. A specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science 1994, 265, 1093-1095. (Pubitemid 24293076)
2. Colotta, V.; Catarzi, D.; Varano, F.; Lenzi, O.; Filacchioni, G.; Costagli, C.; Galli, A.; Ghelardini, C.; Galeotti, N.; Gratteri, P.; et al. Structural Investigation of the 7-Chloro-3-hydroxy-1Hquinazoline-2,4-dione. Scaffold to Obtain AMPA and Kainate Receptor Selective Antagonists. Synthesis, Pharmacological, and Molecular Modeling Studies. J. Med. Chem. 2006, 49, 6015-6026. (Pubitemid 44488537)
3. Malecki, N.; Carato, P.; Rigo, G.; Goossens, J.F.; Houssin, R.; Bailly, C.; Henichart, J.P. Synthesis of condensed quinolines and quinazolines as DNA ligands. Bioorg. Med. Chem. 2004, 12, 641-647. (Pubitemid 38102234)
4. Doyle, L.A.; Ross, D.D. Multidrug resistance mediated by the breast cancer resistance protein BCRP (ABCG2). Oncogene 2003, 22, 7340-7358. (Pubitemid 37487163)
5. Henderson, E.A.; Bavetsias, V.; Theti, D.S.; Wilson, S.C.; Clauss, R.; Jackman, A.L. Targeting the alpha-folate receptor with cyclopenta[g]quinazoline- based inhibitors of thymidylate synthase. Bioorg. Med. Chem. 2006, 14, 5020-5042. (Pubitemid 43767126)
6. Foster, A.; Coffrey, H.A.; Morin, M.J.; Rastinejad, F. Pharmacological rescue of mutant p53 conformation and function. Science 1999, 286, 2507-2510.
7. Chien, T.-C.; Chen, C.-S.; Yu, F.-H.; Chern, J.-W. Nucleosides XI. Synthesis and antiviral evaluation of 5′-alkylthio-5′- deoxyquinazolinone nucleoside derivatives as S-adenosyl-Lhomocysteine analogs. Chem. Pharm. Bull. 2004, 52, 1422-1426. (Pubitemid 41364418)
8. Herget, T.; Freitag, M.; Morbitzer, M.; Kupfer, R.; Stamminger, T.; Marschall, M. Novel chemical class of pUL97 protein kinase-specific inhibitors with strong anticytomegaloviral activity. Antimicrob. Agents Chemother. 2004, 48, 4154-4162. (Pubitemid 39434869)
9. Martin, T.A.; Wheeler, A.G.; Majewski, R.F.; Corrigan, J.R. Sulfanilamidoquinazolines. J. Med. Chem. 1964, 7, 812-814.
10. Kunes, J.; Bazant, J.; Pour, M.; Waisser, K.; Slosarek, M.; Janota, J. Quinazoline derivatives with antitubercular activity. Farmaco 2000, 55, 725-729. (Pubitemid 32037105)
11. Waisser, K.; Gregor, J.; Dostal, H.; Kunes, J.; Kubicova, L.; Klimesova, V.; Kaustova, J. Influence of the replacement of the oxo function with the thioxo group on the antimycobacterial activity of 3-aryl-6,8-dichloro-2H-1,3- benzoxazine-2,4(3H)-diones and 3-arylquinazoline-2,4(1H,3H)-diones. Farmaco 2001, 56, 803-807. (Pubitemid 32913104)
12. Gundla, R.; Kazemi, R.; Sanam, R.; Muttineni, R.; Sarma, J.A.R.P.; Dayam, R.; Neamati, N. Discovery of novel small-molecule inhibitors of human epidermal growth factor receptor-2: Combined ligand and target-based approach. J. Med. Chem. 2008, 51, 3367-3377. (Pubitemid 351874995)
13. Rewcastle, G.W.; Palmer, B.D.; Bridges, A.J.; Showalter, H.D.H.; Sun, L.; Nelson, J.; McMichael, A.; Kraker, A.J.; Fry, D.W.; Denny, W.A. Tyrosine kinase inhibitors. 9. Synthesis and evaluation of fused tricyclic quinazoline analogues as ATP site inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J. Med. Chem. 1996, 39, 918-928. (Pubitemid 26069787)
14. Luth, A.; Lowe, W. Syntheses of 4-(indole-3-yl)quinazolines: A new class of epidermal growth factor receptor tyrosine kinase inhibitors. Eur. J. Med. Chem. 2008, 43, 1478-1488. (Pubitemid 351885214)
15. Mendes da Silva, J.F.; Walters, M.; Al-Damluji, S.; Ganellin, C.R. Molecular features of the prazosin molecule required for activation of Transport-P. Bioorg. Med. Chem. 2008, 16, 7254-7263.
16. Vanelle, P.; de Meo, M.P.; Maldonado, J.; Nouguier, R.; Crozet, M.P.; Laget, M.; Dumenil, G. Genotoxicity in oxazolidine derivatives: Influence of the nitro group. Eur. J. Med. Chem. 1990, 25, 241-250. (Pubitemid 20162002)
17. Crozet, M.P.; Giraud, L.; Sabuco, J.F.; Vanelle, P.; Barreau, M. SRN1 reactions of a tetrasubstituted-1,4-benzoquinone. Tetrahedron Lett. 1991, 32, 4125-4128.
18. Baraldi, P.G.; El-Kashef, H.; Farghaly, A.R.; Vanelle, P.; Fruttarolo, F. Synthesis of new pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines and related heterocycles. Tetrahedron 2004, 60, 5093-5104. (Pubitemid 38624318)
19. Boufatah, N.; Gellis, A.; Maldonado, J.; Vanelle, P. Efficient microwave-assisted synthesis of new sulfonylbenzimidazole-4,7-diones: Heterocyclic quinones with potential antitumor activity. Tetrahedron 2004, 60, 9131-9137. (Pubitemid 39201189)
20. Verhaeghe, P.; Azas, N.; Gasquet, M.; Hutter, S.; Ducros, C.; Laget, M.; Rault, S.; Rathelot, P.; Vanelle, P. Synthesis and antiplasmodial activity of new 4-aryl-2-trichloromethylquinazolines. Bioorg. Med. Chem. Lett. 2008, 18, 396-401.
21. Verhaeghe, P.; Azas, N.; Hutter, S.; Castera-Ducros, C.; Laget, M.; Dumètre, A.; Gasquet, M.; Reboul, J.-P.; Rault, S.; Rathelot, P.; et al. Synthesis and in vitro antiplasmodial evaluation of 4-anilino-2- trichloromethylquinazolines. Bioorg. Med. Chem. 2009, 17, 4313-4322.
22. Kabri, Y.; Azas, N.; Dumètre, A.; Hutter, S.; Laget, M.; Verhaeghe, P.; Gellis, A.; Vanelle, P. Original quinazoline derivatives displaying antiplasmodial properties. Eur. J. Med. Chem. 2010, 45, 616-622.
23. Castera-Ducros, C.; Azas, N.; Verhaeghe, P.; Hutter, S.; Garrigue, P.; Dumètre, A.; Mbatchi, L.; Laget, M.; Remusat, V.; Sifredi, F.; et al. Targeting the human malaria parasite Plasmodium falciparum: In vitro identification of a new antiplasmodial hit in 4-phenoxy-2- trichloromethylquinazoline series. Eur. J. Med. Chem. 2011, 46, 4184-4191.
24. Verhaeghe, P.; Dumètre, A.; Castera-Ducros, C.; Hutter, S.; Laget, M.; Fersing, C.; Prieri, M.; Yzombard, J.; Sifredi, F.; Rault, S.; et al. 4-Thiophenoxy-2-trichloromethyquinazolines display in vitro selective antiplasmodial activity against the human malaria parasite Plasmodium falciparum. Bioorg. Med. Chem. Lett. 2011, 21, 6003-6006.
25. Augart, K.-D.; Kresze, G.; Schönberger, N. 1,6-Cyclisierungen von Phenylimino methyliminokumulenen: Bildung von Chinazolinderivaten. Justus Liebigs Ann. Chem. 1973, 1973, 1457-1466.
26. Ried, W.; Heine, B.; Merkel, W.; Kothe, N. Neuartige Synthese von 4-Tosylimino-3,4-dihydrochinazolin-Derivaten. Synthesis 1976, 1976, 534-535.
27. Nordvall, G.; Yngve, U. Novel Quinazolines as 5-HT6 Modulators II. WO2007108743, 2007.
28. Yokoyama, K.; Ishikawa, N.; Igarashi, S.; Kawano, N.; Masuda, N.; Hamaguchi, W.; Yamasaki, S.; Koganemaru, Y.; Hattori, K.; Miyazaki, T.; et al. Potent and orally bioavailable CCR4 antagonists: Synthesis and structure-activity relationship study of 2-aminoquinazolines. Bioorgan. Med. Chem. 2009, 17, 64-73.
29. Verhaeghe, P.; Rathelot, P.; Gellis, A.; Rault, S.; Vanelle, P. Highly efficient microwave assisted α-trichlorination reaction of α-methylated nitrogen containing heterocycles. Tetrahedron 2006, 62, 8173-8176.