Synthesis of New 2-Phenylamino-4<i>H</i>-chromene-3-carbonitrile Derivatives and Their Effects on Tumor Cell Lines and against Protein Kinases — Oak Academic Publishing
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Synthesis of New 2-Phenylamino-4<i>H</i>-chromene-3-carbonitrile Derivatives and Their Effects on Tumor Cell Lines and against Protein Kinases
Laboratoire de Chimie Appliquée: Hétérocycles, Corps Gras et Polymères, Faculté des Sciences de Sfax, Université de Sfax, Sfax, Tunisie
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Laboratoire de Chimie Appliquée: Hétérocycles, Corps Gras et Polymères, Faculté des Sciences de Sfax, Université de Sfax, Sfax, Tunisie
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Département de Chimie, Collège des Sciences et des Arts, Université de Jouf, Al Qurayyat, KSA
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Institut des Sciences Chimiques de Rennes (ISCR), UMR CNRS 6226, Université de Rennes 1, Campus de Beaulieu, Rennes, France
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Université de Rennes 1, ImPACcell Platform, Campus Villejean, Rennes, France
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Université de Rennes 1, ImPACcell Platform, Campus Villejean, Rennes, France
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Sorbonne Universités, UPMC Université Paris 06, CNRS USR3151, Protein Phosphorylation and Human Disease Unit, KISSf Platform, Station Biologique, Place Georges Teissier, Roscoff, France
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Sorbonne Universités, UPMC Université Paris 06, CNRS USR3151, Protein Phosphorylation and Human Disease Unit, KISSf Platform, Station Biologique, Place Georges Teissier, Roscoff, France
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S2 Wave Platform, ScanMAT UMS 2001CNRS, Université de Rennes 1, Campus de Beaulieu, Rennes, France
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Laboratoire de Chimie Appliquée: Hétérocycles, Corps Gras et Polymères, Faculté des Sciences de Sfax, Université de Sfax, Sfax, Tunisie
1 Laboratoire de Chimie Appliquée: Hétérocycles, Corps Gras et Polymères, Faculté des Sciences de Sfax, Université de Sfax, Sfax, Tunisie
2 Laboratoire de Chimie Appliquée: Hétérocycles, Corps Gras et Polymères, Faculté des Sciences de Sfax, Université de Sfax, Sfax, Tunisie
3 Département de Chimie, Collège des Sciences et des Arts, Université de Jouf, Al Qurayyat, KSA
4 Institut des Sciences Chimiques de Rennes (ISCR), UMR CNRS 6226, Université de Rennes 1, Campus de Beaulieu, Rennes, France
5 Université de Rennes 1, ImPACcell Platform, Campus Villejean, Rennes, France
6 Université de Rennes 1, ImPACcell Platform, Campus Villejean, Rennes, France
7 Sorbonne Universités, UPMC Université Paris 06, CNRS USR3151, Protein Phosphorylation and Human Disease Unit, KISSf Platform, Station Biologique, Place Georges Teissier, Roscoff, France
8 Sorbonne Universités, UPMC Université Paris 06, CNRS USR3151, Protein Phosphorylation and Human Disease Unit, KISSf Platform, Station Biologique, Place Georges Teissier, Roscoff, France
9 S2 Wave Platform, ScanMAT UMS 2001CNRS, Université de Rennes 1, Campus de Beaulieu, Rennes, France
10 Laboratoire de Chimie Appliquée: Hétérocycles, Corps Gras et Polymères, Faculté des Sciences de Sfax, Université de Sfax, Sfax, Tunisie
The synthesis of 2-phenylimino-4 H -chromene-3-carbonitriles 6(a-d) in good overall yields using an efficient and practical methodology in 3 steps has been implemented in this present work. The first step was a heterocyclization between 2-hydroxybenzaldehyde 1 and propanedinitrile 2 which produced 2-iminocoumarin 3 which was submitted to nitrogen/nitrogen displacement in the presence of aromatic primary amine 4 . In the third step, reduction of 5 led to the desired 2-phenylimino-4 H -chromene-3-carbonitriles 6 . Compounds 5(a-d) and 6(a-d) were evaluated for their potential in vitro cytotoxicity against six selected tumor cell lines (Huh7-D12, Caco2, MDA-MB231, HCT 116, PC3 and NCI-H727) and tested for their protein kinase inhibition on eight selected protein kinases. Among them, compounds 5c and 6b exhibited inhibition on HsCK1e ( 5c : 44% and 6b : 42% at 1 μM) and 5c for cytotoxicity on PC3 cell lines (63% at 25 μM).
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-chromene
Nitrogen/Nitrogen Displacement
Protein Kinase Inhibition
Cytotoxicity
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