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Journal articles
Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N -Arylation Reactions and Biological Properties
Madani Hedidi
1
Julien Maillard
1
William Erb
1
Frédéric Lassagne
1
Yury Halauko
2
Oleg Ivashkevich
2
Vadim Matulis
2
Thierry Roisnel
1
Vincent Dorcet
1
Monzer Hamze
3
Ziad Fajloun
3
Blandine Baratte
4
Sandrine Ruchaud
4
Stéphane Bach
4
Ghenia Bentabed-Ababsa
5
Florence Mongin
1
Yury S Halauko 2
Author
Oleg A Ivashkevich 2
Author
Vadim E Matulis 2
Author
Thierry Roisnel 1
Author
Sandrine Ruchaud 4
Author
Stéphane Bach 4
Author
Ghenia Bentabed-Ababsa 5
Author
Florence Mongin 1
Author
1
ISCR - Institut des Sciences Chimiques de Rennes (Campus de Beaulieu - Bât. 10 Avenue du Général Leclerc 35042 Rennes Cedex - France)
- INSA Rennes - Institut National des Sciences Appliquées - Rennes (20, avenue des Buttes de Coësmes - CS 70839 - 35708 Rennes cedex 7 - France)
- CNRS - Centre National de la Recherche Scientifique : UMR6226 (France)
- Ecole Nationale Supérieure de Chimie de Rennes (France)
- UR1 - Université de Rennes 1 (2 rue du Thabor - CS 46510 - 35065 Rennes cedex - France)
- UNIV-RENNES - Université de Rennes (France)
2
Belarusian State University (220030 Avenue Nezalezhnasci 4, Minsk (BELARUS) - Belarus)
3
Centre AZM pour la Recherche en Biotechnologie et ses Applications (Laboratoire Microbiologie, Santé et Environnement, Tripoli - Lebanon)
- Université Libanaise (Lebanon)
4
P3H - Phophorylation de protéines et Pathologies Humaines (Station Biologique de Roscoff Place Georges Teissier 29680 Roscoff - France)
- SBR - Station biologique de Roscoff [Roscoff] (Place Georges Teissier - BP 74 29682 ROSCOFF CEDEX - France)
- UPMC - Université Pierre et Marie Curie - Paris 6 (4 place Jussieu - 75005 Paris - France)
- CNRS - Centre National de la Recherche Scientifique : FR2424 (France)
- UPMC - Université Pierre et Marie Curie - Paris 6 (4 place Jussieu - 75005 Paris - France)
- CNRS - Centre National de la Recherche Scientifique : USR3151 (France)
5
LSOA - Laboratoire de Synthèse Organique Appliquée (Département de Chimie, Bp 1524 El M'Naouer, Oran 31000 - Algeria)
- Université d'Oran 1 Ahmed Ben Bella [Oran] (BP 1524 ELM_Naouer 31000 oran - Algeria)
Abstract : Various aromatic ketones were first functionalized next to the carbonyl function by deprotolithiation in the presence of a zinc salt followed by iodolysis. The outcome of the reactions was analyzed, and in particular their regioselectivity in the light of the calculated pKa values. The various halogenated ketones were next involved in copper-catalyzed twofold C-N bond formation in order to obtain fused systems based on 2-aminopyrimidines. Besides potential antibacterial effect, reached 2-aminobenzothiopyrano[4,3,2-de]quinazoline proved to inhibit PIM1 (IC50: 0.61 μM) and CDK2/cyclin A (IC50: 2.0 μM) kinases.
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Journal articles
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01624382
Contributor : Laurent Jonchère <>
Submitted on : Thursday, October 26, 2017 - 11:40:48 AM
Last modification on : Wednesday, January 13, 2021 - 3:39:58 AM
Long-term archiving on: : Saturday, January 27, 2018 - 1:05:36 PM
Contributor : Laurent Jonchère <>
Submitted on : Thursday, October 26, 2017 - 11:40:48 AM
Last modification on : Wednesday, January 13, 2021 - 3:39:58 AM
Long-term archiving on: : Saturday, January 27, 2018 - 1:05:36 PM
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Identifiers
- HAL Id : hal-01624382, version 1
- DOI : 10.1002/ejoc.201701004
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UNIV-RENNES1 | ISCR | CNRS | SCR-CD | ISCR-PRATS | UR1-UFR-SPM | INC-CNRS | P3H | UPMC | ISCR-CORINT | UNIV-RENNES | INSA-GROUPE | SORBONNE-UNIVERSITE | SU-SCIENCES | FR2424 | INSA-RENNES | LBI2M | SU-TI
Citation
Madani Hedidi, Julien Maillard, William Erb, Frédéric Lassagne, Yury Halauko, et al.. Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N -Arylation Reactions and Biological Properties. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2017, 2017 (39), pp.5903-5915. ⟨10.1002/ejoc.201701004⟩. ⟨hal-01624382⟩
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