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Your search keyword '"thiazolo[5,4-f]quinazolin-9(8H)-ones"' showing total 8 results
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8 results on '"thiazolo[5,4-f]quinazolin-9(8H)-ones"'

1. Development of Kinase Inhibitors via Metal-Catalyzed C-H Arylation of 8-Alkyl-thiazolo[5,4-f]-quinazolin-9-ones Designed by Fragment-Growing Studies.

Author

Couly, Florence, Harari, Marine, Dubouilh-Benard, Carole, Bailly, Laetitia, Petit, Emilie, Diharce, Julien, Bonnet, Pascal, Meijer, Laurent, Fruit, Corinne, and Besson, Thierry

Subjects
*KINASE inhibitors, *NILOTINIB, *METAL catalysts, *QUINAZOLINE, *AROMATIC compounds
Abstract

Efficient metal catalyzed C-H arylation of 8-alkyl-thiazolo[5,4-f]-quinazolin-9-ones was explored for SAR studies. Application of this powerful chemical tool at the last stage of the synthesis of kinase inhibitors allowed the synthesis of arrays of molecules inspired by fragment-growing studies generated by molecular modeling calculations. Among the potentially active compounds designed through this strategy, FC162 (4c) exhibits nanomolar IC50 values against some kinases, and is the best candidate for the development as a DYRK kinase inhibitor. [ABSTRACT FROM AUTHOR]

Published
2018
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2. Development of Kinase Inhibitors via Metal-Catalyzed C–H Arylation of 8-Alkyl-thiazolo[5,4-f]-quinazolin-9-ones Designed by Fragment-Growing Studies

Author

Florence Couly, Marine Harari, Carole Dubouilh-Benard, Laetitia Bailly, Emilie Petit, Julien Diharce, Pascal Bonnet, Laurent Meijer, Corinne Fruit, and Thierry Besson

Subjects
thiazolo[5,4-f]quinazolin-9(8H)-ones, microwave-assisted synthesis, C–H arylation, protein kinases, DYRK1A, CDK5, GSK-3, CLK1, CK1, Organic chemistry, QD241-441
Abstract

Efficient metal catalyzed C–H arylation of 8-alkyl-thiazolo[5,4-f]-quinazolin-9-ones was explored for SAR studies. Application of this powerful chemical tool at the last stage of the synthesis of kinase inhibitors allowed the synthesis of arrays of molecules inspired by fragment-growing studies generated by molecular modeling calculations. Among the potentially active compounds designed through this strategy, FC162 (4c) exhibits nanomolar IC50 values against some kinases, and is the best candidate for the development as a DYRK kinase inhibitor.

Published
2018
Full Text
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3. Synthesis of Bioactive 2-(Arylamino)thiazolo[5,4-f]-quinazolin-9-ones via the Hügershoff Reaction or Cu- Catalyzed Intramolecular C-S Bond Formation

Author

Damien Hédou, Carole Dubouilh-Benard, Nadège Loaëc, Laurent Meijer, Corinne Fruit, and Thierry Besson

Subjects
Hügershoff reaction, thiazolo[5,4-f]quinazolin-9(8H)-ones, microwave-assisted synthesis, protein kinases, CDK5, GSK-3, CLK1, CK1, DYRK1A, Organic chemistry, QD241-441
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.

Published
2016
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4. Synthesis of Thiazolo[5,4-f]quinazolin-9(8H)-ones as Multi-Target Directed Ligands of Ser/Thr Kinases

Author

Damien Hédou, Julien Godeau, Nadège Loaëc, Laurent Meijer, Corinne Fruit, and Thierry Besson

Subjects
thiazolo[5,4-f]quinazolin-9(8H)-ones, multi-target-directed ligand, protein kinases, microwave-assisted synthesis, CDK5, GSK-3, CLK1, CK1, DYRK1A., Organic chemistry, QD241-441
Abstract

A library of thirty novel thiazolo[5,4-f]quinazolin-9(8H)-one derivatives belonging to four series designated as 12, 13, 14 and 15 was efficiently prepared, helped by microwave-assisted technology when required. The efficient multistep synthesis of methyl 6-amino-2-cyano- benzo[d]thiazole-7-carboxylate (1) has been reinvestigated and performed on a multigram scale. The inhibitory potency of the final products against five kinases involved in Alzheimer’s disease was evaluated. This study demonstrates that some molecules of the 12 and 13 series described in this paper are particularly promising for the development of new multi-target inhibitors of kinases.

Published
2016
Full Text
View/download PDF

5. Development of Kinase Inhibitors via Metal-Catalyzed C–H Arylation of 8-Alkyl-thiazolo[5,4-f]-quinazolin-9-ones Designed by Fragment-Growing Studies

Author

Laetitia Bailly, Emilie Petit, Corinne Fruit, Marine Harari, Thierry Besson, Julien Diharce, Laurent Meijer, Carole Dubouilh-Benard, Florence Couly, Pascal Bonnet, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Nice (ICN), Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Côte d'Azur (UCA), Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans (UO)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut de Chimie du CNRS (INC)-Institut National de la Santé et de la Recherche Médicale (INSERM), ManRos Therapeutics, Institut de Chimie Organique Fine (IRCOF), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Nice Sophia Antipolis (1965 - 2019) (UNS), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Models, Molecular, thiazolo[5,4-f]quinazolin-9(8H)-ones, Molecular model, C-H arylation, Pharmaceutical Science, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 01 natural sciences, microwave-assisted synthesis, Analytical Chemistry, CLK1, GSK-3, Drug Discovery, Microwaves, chemistry.chemical_classification, thiazolo[5, Molecular Structure, Kinase, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Protein-Tyrosine Kinases, 3. Good health, Molecular Docking Simulation, Chemistry (miscellaneous), Molecular Medicine, Casein kinase 1, C–H arylation, CK1, CDK5, Protein Serine-Threonine Kinases, Article, lcsh:QD241-441, Structure-Activity Relationship, lcsh:Organic chemistry, Molecule, Physical and Theoretical Chemistry, Protein Kinase Inhibitors, Alkyl, 4-f ]quinazolin-9(8H)-ones, protein kinases, 010405 organic chemistry, Cyclin-dependent kinase 5, Organic Chemistry, DYRK1A, Combinatorial chemistry, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, chemistry, Quinazolines
Abstract

Efficient metal catalyzed C&ndash, H arylation of 8-alkyl-thiazolo[5,4-f]-quinazolin-9-ones was explored for SAR studies. Application of this powerful chemical tool at the last stage of the synthesis of kinase inhibitors allowed the synthesis of arrays of molecules inspired by fragment-growing studies generated by molecular modeling calculations. Among the potentially active compounds designed through this strategy, FC162 (4c) exhibits nanomolar IC50 values against some kinases, and is the best candidate for the development as a DYRK kinase inhibitor.

Published
2018

6. Synthesis of Thiazolo[5,4-f]quinazolin-9(8H)-ones as Multi-Target Directed Ligands of Ser/Thr Kinases

Author

Laurent Meijer, Damien Hédou, Nadège Loaëc, Corinne Fruit, Thierry Besson, Julien Godeau, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Phophorylation de protéines et Pathologies Humaines (P3H), Station biologique de Roscoff [Roscoff] (SBR), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), ManRos Therapeutics, Institut de Chimie Organique Fine (IRCOF), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), and Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
0301 basic medicine, thiazolo[5,4-f]quinazolin-9(8H)-ones, Swine, Pharmaceutical Science, Ligands, 01 natural sciences, microwave-assisted synthesis, Analytical Chemistry, CLK1, Multi target, multi-target-directed ligand, Drug Discovery, GSK-3, thiazolo[5, Molecular Structure, Kinase, Chemistry, 4-f]quinazolin-9(8H)-ones, Inhibitory potency, Chemistry (miscellaneous), Molecular Medicine, DYRK1A, Casein kinase 1, Stereochemistry, CK1, CDK5, Protein Serine-Threonine Kinases, Article, lcsh:QD241-441, 03 medical and health sciences, lcsh:Organic chemistry, Alzheimer Disease, Animals, Humans, [CHIM]Chemical Sciences, Physical and Theoretical Chemistry, Protein Kinase Inhibitors, Quinazolinones, 4-f ]quinazolin-9(8H)-ones, protein kinases, Protein-Serine-Threonine Kinases, 010405 organic chemistry, Organic Chemistry, Combinatorial chemistry, 0104 chemical sciences, Thiazoles, 030104 developmental biology
Abstract

International audience; A library of thirty novel thiazolo[5,4-f]quinazolin-9(8H)-one derivatives belonging to four series designated as 12, 13, 14 and 15 was efficiently prepared, helped by microwave-assisted technology when required. The efficient multistep synthesis of methyl 6-amino-2-cyano- benzo[d]thiazole-7-carboxylate (1) has been reinvestigated and performed on a multigram scale. The inhibitory potency of the final products against five kinases involved in Alzheimer’s disease was evaluated. This study demonstrates that some molecules of the 12 and 13 series described in this paper are particularly promising for the development of new multi-target inhibitors of kinases

Published
2016

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

Author

Hédou D, Dubouilh-Benard C, Loaëc N, Meijer L, Fruit C, and Besson T

Subjects
Alzheimer Disease enzymology, Barbiturates chemistry, Catalysis, Copper chemistry, Humans, Molecular Structure, Protein Kinase Inhibitors chemical synthesis, Protein Kinase Inhibitors isolation & purification, Protein Kinase Inhibitors therapeutic use, Quinazolinones chemical synthesis, Quinazolinones therapeutic use, Structure-Activity Relationship, Alzheimer Disease drug therapy, Protein Kinase Inhibitors chemistry, Quinazolinones chemistry
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.

Published
2016
Full Text
View/download PDF

8. Synthesis of Thiazolo[5,4-f]quinazolin-9(8H)-ones as Multi-Target Directed Ligands of Ser/Thr Kinases.

Author

Hédou D, Godeau J, Loaëc N, Meijer L, Fruit C, and Besson T

Subjects
Animals, Humans, Ligands, Molecular Structure, Protein Kinase Inhibitors metabolism, Protein Kinase Inhibitors therapeutic use, Protein Serine-Threonine Kinases metabolism, Quinazolinones metabolism, Quinazolinones therapeutic use, Swine, Thiazoles metabolism, Thiazoles therapeutic use, Alzheimer Disease drug therapy, Protein Kinase Inhibitors chemical synthesis, Protein Serine-Threonine Kinases antagonists & inhibitors, Quinazolinones chemical synthesis, Thiazoles chemical synthesis
Abstract

A library of thirty novel thiazolo[5,4-f]quinazolin-9(8H)-one derivatives belonging to four series designated as 12, 13, 14 and 15 was efficiently prepared, helped by microwave-assisted technology when required. The efficient multistep synthesis of methyl 6-amino-2-cyano- benzo[d]thiazole-7-carboxylate (1) has been reinvestigated and performed on a multigram scale. The inhibitory potency of the final products against five kinases involved in Alzheimer's disease was evaluated. This study demonstrates that some molecules of the 12 and 13 series described in this paper are particularly promising for the development of new multi-target inhibitors of kinases.

Published
2016
Full Text
View/download PDF

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