Design and synthesis of thiazolo[5,4-f]quinazolines as DYRK1A inhibitors, part I

Molecules

Volumn 19, Issue 10, 2014, Pages 15546-15571

  Foucourt, Alicia ^a   Hédou, Damien ^a   Dubouilh Benard, Carole ^a   Désiré, Laurent ^b   Casagrande, Anne Sophie ^b   Leblond, Bertrand ^b   Loäec, Nadège ^c,d   Meijer, Laurent ^d   Besson, Thierry ^a  

^a NORMANDIE UNIVERSITÉ   (France)

^b Diaxonhit   (France)

^c STATION BIOLOGIQUE   (France)

^d Centre de Perharidy   (France)

Author keywords

Appel salt; Dimroth rearrangement; DYRK1A; GSK3 ; Kinases inhibitors; Microwave assisted chemistry; Thiazolo 5,4 f quinazolines

Indexed keywords

DYRK KINASE; PROTEIN KINASE INHIBITOR; PROTEIN SERINE THREONINE KINASE; PROTEIN TYROSINE KINASE; QUINAZOLINE DERIVATIVE; THIAZOLE DERIVATIVE;

ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; HUMAN; IC50; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG DESIGN; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; PROTEIN-SERINE-THREONINE KINASES; PROTEIN-TYROSINE KINASES; QUINAZOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 84907494554     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules191015546     Document Type: Article

References (29)

1. Martin, L.; Latypova, X.; Wilson, C. M.; Magnaudeix, A.; Perrin, M.-L.; Terro, F. Tau protein kinases: Involvement in Alzheimer's disease. Ageing Res. Rev. 2013, 12, 289-309.
2. Flajolet, M.; He, G.; Heiman, M.; Lin, A.; Nairn, A. C.; Greengard, P. Regulation of Alzheimer's disease amyloid-β formation by casein kinase I. Proc. Nat. Acad. Sci. USA 2007, 104, 4159-4164.
3. Weinmann, H.; Metternich, R. Drug discovery process for kinase Inhibitors. ChemBioChem 2005, 6, 455-459;
4. this paper is the editorial of a special issue "Kinases in drug discovery" Chem BioChem 2005, 6, 453-574.
5. Loidreau, Y.; Marchand, P.; Dubouilh-Benard, C.; Nourrisson, M.-R.; Duflos, M.; Loaëc, N.; Meijer, L.; Besson, T. Synthesis and biological evaluation of N-aryl-7-methoxybenzo[b]furo[3, 2-d]pyrimidin-4-amines and their N-arylbenzo[b]thieno[3, 2-d]pyrimidin-4-amine analogues as dual inhibitors of CLK1 and DYRK1A kinases. Eur. J. Med. Chem. 2013, 59, 283-295.
6. Loidreau, Y.; Marchand, P.; Dubouilh-Benard, C.; Nourrisson, M.-R.; Duflos, M.; Lozach, O.; Loaëc, N.; Meijer, L.; Besson, T. Synthesis and biological evaluation of N-arylbenzo[b]thieno[3, 2-d]pyrimidin-4-amines and their pyrido and pyrazino analogues as Ser/Thr kinase inhibitors. Eur. J. Med. Chem. 2012, 58, 171-183.
7. Foucourt, A.; Dubouilh-Benard, C.; Chosson, E.; Corbière, C.; Buquet, C.; Iannelli, M.; Leblond, B.; Marsais, F.; Besson, T. Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent. Tetrahedron 2010, 66, 4495-4502.
8. Logé, C.; Testard, A.; Thiéry, V.; Lozach, O.; Blairvacq, M.; Robert, J.-M.; Meijer, L.; Besson, T. Novel 9-oxo-thiazolo[5, 4-f]quinazoline-2-carbonitrile derivatives as dual cyclin-dependent kinase 1 (CDK1)/glycogen synthase kinase-3 (GSK-3) inhibitors: synthesis, biological evaluation and molecular modeling studies. Eur. J. Med. Chem. 2008, 43, 1469-1477.
9. Testard, A.; Logé, C.; Léger, B.; Robert, J.-M.; Lozach, O.; Blairvacq, M.; Meijer, L.; Thiéry, V.; Besson, T. Thiazolo[5, 4-f]quinazolin-9-ones, inhibitors of glycogen synthase kinase-3. Bioorg. Med. Chem. Lett. 2006, 16, 3419-3423.
10. Alexandre, F. R.; Berecibar, A.; Wrigglesworth, R.; Besson, T. Efficient synthesis of thiazoloquinazolinone derivatives. Tetrahedron Lett. 2003, 44, 4455-4458.
11. Besson, T.; Guillard, J.; Rees, C. W. Multistep Synthesis of Thiazoloquinazolines under Microwave Irradiation in Solution. Tetrahedron Lett. 2000, 41, 1027-1030.
12. For a complete review see: Harris, C. S.; Hennequin, L.; Morgentin, R.; Pasquet, G. Synthesis and functionnalization of 4-substituted quinazolines as kinases templates. In Targets in Heterocyclic Systems-Chemistry and Properties; Attanasi, O. A., Spinelli, D., Eds.; Italian Society of Chemistry: Roma, Italia, 2010; Volume 14, pp. 315-350.
13. Alexandre, F. R.; Domon, L.; Frère, S.; Testard, A.; Thiéry, V.; Besson, T. Microwaves in drug discovery and multi-step synthesis. Mol. Divers. 2003, 7, 273-280.
14. Guillon, R.; Pagniez, F.; Picot, C.; Hédou, D.; Tonnerre, A.; Chosson, E.; Duflos, M.; Besson, T.; Logé, C.; Le Pape, P. Discovery of a Novel Broad-spectrum Antifungal Agent, Derived from Albaconazole. ACS Med. Chem. Lett. 2013, 4, 288-292.
15. Hédou, D.; Guillon, R.; Lecointe, C.; Logé, C.; Chosson, E.; Besson, T. Novel synthesis of angular thiazolo[5, 4-f] and [4, 5-h]quinazolines, preparation of their linear thiazolo[4, 5-g] and [5, 4-g]quinazoline analogs. Tetrahedron 2013, 69, 3182-3191.
16. Deau, E.; Hédou, D.; Chosson, E.; Levacher, V.; Besson, T. Convenient one-pot synthesis of N3-substituted pyrido[2, 3-d]-, pyrido[3, 4-d]-, pyrido[4, 3-d]-pyrimidin-4 (3H)-ones, and quinazolin-4 (3H)-ones analogs. Tetrahedron Lett. 2013, 54, 3518-3521.
17. Besson, T.; Dozias, M. J.; Guillard, J.; Rees, C. W. New Route to 2-Cyanobenzothiazoles via N-Arylimino-1, 2, 3-dithiazoles. J. Chem. Soc. Perkin Trans. 1 1998, 3925-3926.
18. Loidreau, Y.; Melissen, S.; Levacher, V.; Logé, C.; Graton, J.; Le Questel, J. Y.; Besson, T. Study of N1-alkylation of indoles from the reaction of 2 (or 3)-aminoindole-3-(or 2) carbonitriles with DMF-dialkylacetals. Org. Biomol. Chem. 2012, 20, 4916-4925.
19. Giraud, F.; Alves, G.; Debiton, E.; Nauton, L.; Théry, V.; Durieu, E.; Ferandin, Y.; Lozach, O.; Meijer, L.; Anizon, F.; et al. Synthesis, protein kinase inhibitory potencies, and in vitro antiproliferative activities of meridianin derivatives. J. Med. Chem. 2011, 54, 4474-4489.
20. Bach, S.; Knockaert, M.; Reinhardt, J.; Lozach, O.; Schmitt, S.; Baratte, B.; Koken, M.; Coburn, P.; Tang, L.; Jiang, T.; et al. Roscovitine targets, protein kinases and pyridoxal kinase. J. Biol. Chem. 2005, 280, 31208-31219.
21. Bidd, J. A.; Snyder, G. L.; Greengard, P.; Biernat, J.; Wu, Y.-Z.; Mandelkow, E.-M.; Eisenbrand, G.; Meijer, L. Indirubins inhibit glycogen synthase kinase-3β and CDK5/P25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer's Disease: A property common to most cyclin-dependent kinase inhibitors? J. Biol. Chem. 2001, 276, 251-260.
22. Primot, A.; Baratte, B.; Gompel, M.; Borgne, A.; Liabeuf, S.; Romette, J. L.; Jho, E. H.; Costantini, F.; Meijer, L. Purification of GSK-3 by affinity chromatography on immobilized axin. Protein Expr. Purif. 2000, 20, 394-404.
23. Reinhardt, J.; Ferandin, Y.; Meijer, L. Purification of CK1 by affinity chromatography on immobilised axin. Protein Expr. Purif. 2007, 54, 101-109.
24. Patel, K.; Gadewar, M.; Tripathi, R.; Prasad, S. K.; Patel, D. K. A review on medicinal importance, pharmacological activity and bioanalytical aspects of beta-carboline alkaloid "Harmine". Asian Pac. J. Trop. Biomed. 2012, 2, 660-664.
25. Debdab, M.; Carreaux, F.; Renault, S.; Soundararajan, M.; Fedorov, O.; Filippakopoulos, P.; Lozach, O.; Babault, L.; Tahtouh, T.; Baratte, B.; et al. Leucettines, a class of potent inhibitors of cdc2-like kinases and dual specificity, tyrosine phosphorylation regulated kinases derived from the marine sponge leucettamine B. Modulation of alternative pre-RNA splicing. J. Med. Chem. 2011, 54, 4172-4186.
26. Tahtouh, T.; Elkins, J. M.; Filippakopoulos, P.; Soundararajan, M.; Burgy, G.; Durieu, E.; Cochet, C.; Schmid, R. S.; Lo, D. C.; Delhommel, F.; et al. Selectivity, co-crystal structures and neuroprotective properties of Leucettines, a family of protein kinase inhibitors derived from the marine sponge alkaloid Leucettamine B. J. Med. Chem. 2012, 55, 9312-9330.
27. Frederick, R.; Bruyere, C.; Vancraeynest, C.; Reniers, J.; Meinguet, C.; Pochet, L.; Backlund, A.; Masereel, B.; Kiss, R.; Wouters, J. Novel Trisubstituted Harmine Derivatives with Original in Vitro Anticancer Activity. J. Med. Chem. 2012, 55, 6489-6501.
28. Armen Instrument. Available online: http://www.armen-instrument.com (accessed on 24 September 2014).
29. Leblond, B.; Casagrande, A.-S.; Desire, L.; Foucourt, A.; Besson, T. DYRK1 Inhibitors and Uses Thereof. U. S. Patent20, 140, 275, 064, 18 September 2014.