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Molecules 2016, 21(6), 794; doi:10.3390/molecules21060794

Synthesis of Bioactive 2-(Arylamino)thiazolo[5,4-f]-quinazolin-9-ones via the Hügershoff Reaction or Cu- Catalyzed Intramolecular C-S Bond Formation

1
Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA, 76000 Rouen, France
2
Protein Phosphorylation & Human Disease group, Station Biologique, 29680 Roscoff, France
3
Manros Therapeutics, Centre de Perharidy, 29680 Roscoff, France
*
Author to whom correspondence should be addressed.
Academic Editor: Philippe Belmont
Received: 22 April 2016 / Revised: 12 June 2016 / Accepted: 13 June 2016 / Published: 18 June 2016
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

A library of thirty eight novel thiazolo[5,4-f]quinazolin-9(8H)-one derivatives (series 8, 10, 14 and 17) was prepared via the Hügershoff reaction and a Cu catalyzed intramolecular C-S bond formation, helped by microwave-assisted technology when required. The efficient multistep synthesis of the key 6-amino-3-cyclopropylquinazolin-4(3H)-one (3) has been reinvestigated and performed on a multigram scale from the starting 5-nitroanthranilic acid. The inhibitory potency of the final products was evaluated against five kinases involved in Alzheimer’s disease and showed that some molecules of the 17 series described in this paper are particularly promising for the development of novel multi-target inhibitors of kinases. View Full-Text
Keywords: Hügershoff reaction; thiazolo[5,4-f]quinazolin-9(8H)-ones; microwave-assisted synthesis; protein kinases; CDK5; GSK-3; CLK1; CK1; DYRK1A Hügershoff reaction; thiazolo[5,4-f]quinazolin-9(8H)-ones; microwave-assisted synthesis; protein kinases; CDK5; GSK-3; CLK1; CK1; DYRK1A
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Hédou, D.; Dubouilh-Benard, C.; Loaëc, N.; Meijer, L.; Fruit, C.; Besson, T. Synthesis of Bioactive 2-(Arylamino)thiazolo[5,4-f]-quinazolin-9-ones via the Hügershoff Reaction or Cu- Catalyzed Intramolecular C-S Bond Formation. Molecules 2016, 21, 794.

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