Oussama Dehbi - Academia.edu (original) (raw)
Papers by Oussama Dehbi
ChemInform, Feb 12, 2013
Two sequential cross-coupling reactions of substrate (I) with arylboronic acids allow the approac... more Two sequential cross-coupling reactions of substrate (I) with arylboronic acids allow the approach to the desired target compounds.
Products belonging to the pyridopyrimidine family are characterized by their intense use in pharm... more Products belonging to the pyridopyrimidine family are characterized by their intense use in pharmacology. The increase of interest for this heterocyclic scaffold prompted different research teams around the world to study their chemically and biologically properties. In this work, we are interested in the functionalization of pyridopyrimidines and, more specifically, of the less described regioisomer, namely pyrido[3,2-d]pyrimidines. The target compounds were synthesized from 2,7-dichloropyrido[3,2-d]pyrimidine via nucleophilic aromatic substitution and palladium-catalyzed couplings and, in order to obtain potent kinases inhibitors. Our goal has been achieved with several elaborate molecules. These bioactive compounds inhibit kinases such as Cyclin Dependant Kinases (CDK), Glycogen Synthase 3 (GSK3) or Dual specificity tYRosine-phosphorylation-regulated Kinase 1A (DYRK1A) in the nanomolar range. These biological targets are mainly involved in degenerative process or down syndrome. These pharmacological results led us to extend our studies to other pyridopyrimidines, namely pyrido[2,3-d]pyrimidines as well as other types of polynitrogenated bicycles, namely imidazo[1,2- a]pyridine and imidazo[1,2-b]pyridazine.
Polycyclic Aromatic Compounds, Apr 19, 2022
The hydroxyapatite nanoparticles (HANPs) were prepared by microwave assisted coprecipitation meth... more The hydroxyapatite nanoparticles (HANPs) were prepared by microwave assisted coprecipitation method and assessed their efficacy on flocculation of microalga, Chlorella vulgaris. The co-precipitation was initiated by mixing the Ca(OH) 2 and H 3 PO 4 and allowed 2 them to form the HANPs through exposure of microwave irradiation at 10 min (HA1) and 15 min (HA2). In which the 15 min (HA2) exposure showed the better and stable formation of the HANPs. The results showed the both HANPs was found to be needle-shaped and size from 15 to 50 nm evident by TEM analysis and its crystallinity was confirmed by XRD analysis. The addition of 300 mg. mL-1 of HA2 enhanced the flocculation of C. vulgaris with the efficiency of 90% in 60 min. Hence, this work proposed that use of HANPs in flocculation procedures is a more promising and cost-effective method for microalgal biomass harvesting.
![Research paper thumbnail of Synthesis, antimicrobial evaluation, crystal structure, Hirschfeld surface analysis and docking studies of 4-[2-(1-methyl-1H-imidazol-2-ylsulfanyl)-acetylamino]-benzenesulfonic acid](https://attachments.academia-assets.com/109637926/thumbnails/1.jpg)
](Journal of Molecular Structure, Oct 1, 2022
HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific re... more HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.
![Research paper thumbnail of Regioselective Syntheses of 2,7-(Het)Arylpyrido[2,3-d]pyrimidines by an Orthogonal Cross-Coupling Strategy](https://attachments.academia-assets.com/109639922/thumbnails/1.jpg)
](Synlett, Sep 13, 2012
Regioselective syntheses of 1,4,5-trisubstituted 1,2,3-triazoles were accomplished by three diffe... more Regioselective syntheses of 1,4,5-trisubstituted 1,2,3-triazoles were accomplished by three different strategies, relying on (i) the interception of stoichiometrically formed 5-cuprated-1,2,3-triazoles, (ii) the use of stoichiometrically functionalized alkynes or (iii) catalytic C-H bond functionalizations. This perspective article summarizes progress in this research area until June 2010.
Polycyclic Aromatic Compounds
Les produits appartenant à la famille des pyridopyrimidines sont caractérisés par leur intense ut... more Les produits appartenant à la famille des pyridopyrimidines sont caractérisés par leur intense utilisation dans le domaine pharmacologique, ce qui a poussé différentes équipes de recherche, de par le monde, à les étudier chimiquement et biologiquement. Dans ce travail, nous nous sommes intéressés au groupe des pyridopyrimidines et, plus particulièrement, à l’isomère le moins décrit dans la littérature, à savoir les pyrido[3,2-d]pyrimidines. Les composés ciblés sont synthétisés à partir de la 2,7-dichloropyrido[3,2-d]pyrimidine, via des substitutions nucléophiles aromatiques et des couplages pallado-catalysés et ce, dans le but d’obtenir de puissants inhibiteurs de kinases. Ce but a été atteint puisqu’en effet plusieurs des molécules élaborées inhibent les kinases testées avec des concentrations de l’ordre du nanomolaire. Des résultats pharmacologiques aussi concluants nous ont amenés à étendre nos études à d’autres pyridopyrimidines, à savoir les pyrido[2,3-d]pyrimidines ainsi qu’à ...
![Research paper thumbnail of Synthesis, antimicrobial evaluation, crystal structure, Hirschfeld surface analysis and docking studies of 4-[2-(1-methyl-1H-imidazol-2-ylsulfanyl)-acetylamino]-benzenesulfonic acid](https://attachments.academia-assets.com/109637983/thumbnails/1.jpg)
](Journal of Molecular Structure
HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific re... more HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.
An efficient synthesis of 1,3-oxazine and 1,3-thiazine derivatives has been demonstrated through ... more An efficient synthesis of 1,3-oxazine and 1,3-thiazine derivatives has been demonstrated through a one-pot multicomponent condensation reaction (MCR). Urea and thiourea have been used as reagent and catalyst system for this reaction. The method produced good to excellent product yields. The synthesized compounds were evaluated for their antibacterial and antifungal activities in vitro against four bacteria and two fungi.
Products belonging to the pyridopyrimidine family are characterized by their intense use in pharm... more Products belonging to the pyridopyrimidine family are characterized by their intense use in pharmacology. The increase of interest for this heterocyclic scaffold prompted different research teams around the world to study their chemically and biologically properties. In this work, we are interested in the functionalization of pyridopyrimidines and, more specifically, of the less described regioisomer, namely pyrido[3,2-d]pyrimidines. The target compounds were synthesized from 2,7-dichloropyrido[3,2-d]pyrimidine via nucleophilic aromatic substitution and palladium-catalyzed couplings and, in order to obtain potent kinases inhibitors. Our goal has been achieved with several elaborate molecules. These bioactive compounds inhibit kinases such as Cyclin Dependant Kinases (CDK), Glycogen Synthase 3 (GSK3) or Dual specificity tYRosine-phosphorylation-regulated Kinase 1A (DYRK1A) in the nanomolar range. These biological targets are mainly involved in degenerative process or down syndrome. T...
The present invention relates to a compound of the following general formula (I): embedded image ... more The present invention relates to a compound of the following general formula (I): embedded image in which: R 1 is in particular H, a halogen atom or an aryl group; R 2 is in particular a halogen atom or an aryl group, R 3 is in particular a halogen atom or an aryl or heteroaryl group, as well as its pharmaceutically acceptable salts, its hydrates or its polymorphic crystalline structures, its racemates, diastereoisomers or enantiomers.
Polycyclic Aromatic Compounds, 2021
Journal of Environmental Chemical Engineering, 2021
Abstract Solvents and catalysts are among the key factors in achieving the green chemical synthes... more Abstract Solvents and catalysts are among the key factors in achieving the green chemical synthesis of bioactive compounds. In this regard, metal-doped nanoparticles, as a heterogeneous catalyst, in urea-based deep eutectic mixtures were used to prepare a series of pyrrolidinone-substituted benzothiazoles. In the strategy developed herein, pyrrolidinone derivatives were synthesized by reacting different arylamines with dimethyl itaconate using water as the solvent in a microwave. Then, the as-obtained pyrrolidinone derivatives were reacted with 2-aminothiophenol under microwave irradiation with the assistance of a deep eutectic mixture (CuCl2 or NiCl2/urea) and Cu- or Ni-doped TiO2 nanoparticles to afford the final derivative incorporating both pyrrolidin-2-one and benzothiazole rings. To determine the optimum reaction conditions, the effect of temperature, solvent nature, and reaction time was investigated. Under the optimal operation conditions, high reaction yields were achieved. The developed strategy exhibited advantages of a short reaction time, eco-friendliness, and high productivity. Finally, the obtained derivatives were examined in terms of their antibacterial potential against selected Gram-negative and Gram-positive bacterial strains: Eight of the derivatives exhibited activity against the tested bacteria.
Materials Chemistry and Physics, 2021
• Copper and nickel single-doped TiO 2 nanostructures were successfully prepared. • Structures, e... more • Copper and nickel single-doped TiO 2 nanostructures were successfully prepared. • Structures, elemental compositions and morphologies were characterized. • The catalytic performance of the Cu-doped and Ni-doped TiO 2 nanostructures were evaluated. • The pyridopyrimidine derivatives was prepared using doped TiO 2 nanostructures.
Green Chemistry Letters and Reviews, 2018
An efficient and ecofriendly method for the synthesis of disubstituted 5-aminopyrimidines from vi... more An efficient and ecofriendly method for the synthesis of disubstituted 5-aminopyrimidines from vinyl azides and urea or thiourea was developed. This reaction proceeds under microwave irradiation conditions in the presence of water as a solvent. The remarkable features of this new protocol are high conversion, short reaction times, cleaner reaction profiles and straightforward procedure.
Current Organic Chemistry, 2018
Green Chemistry Letters and Reviews, 2018
An eco-friendly and efficient method was developed for the preparation of a new series of sulfurc... more An eco-friendly and efficient method was developed for the preparation of a new series of sulfurcontaining quinolinthiones. Compounds 6a-o were synthesized from 4-methyl-2-thiocoumarin and arylhydrazides using water as a solvent under microwave irradiation. Some noteworthy features of our novel method are its cleanliness, short reaction time and high conversion rate, and the reaction proceeds (profiles) using a simple procedure. All of the prepared compounds were screened for their antibacterial efficacy in vitro using the disc diffusion method against bacterial strains. Compound (6j) showed the greatest potency with a 16 and 19 mm inhibition zone against Klebsiella pneumonia and Staphylococcus aureus, respectively.
Green Chemistry Letters and Reviews, 2017
Animal-bone-meal-supported palladium (0) was prepared and used as catalyst in the Suzuki coupling... more Animal-bone-meal-supported palladium (0) was prepared and used as catalyst in the Suzuki coupling reaction in water, under sunlight as an alternative source of energy. This palladium has showed a high catalytic activity than tetrakis(triphenylphosphine) palladium (Pd(PPh 3) 4) in the Suzuki cross-coupling reaction (the reaction of 4-halogenopyridopyrimidine with boronic acids) in water via sunlight as the light source, with no addition of ligands. This green method affords heteroaryls with excellent yields in comparison with the classical method using tetrakis (triphenylphosphine) palladium. The green catalyst did not show any significant loss of activity, even when used up to five times.
ChemInform, Feb 12, 2013
Two sequential cross-coupling reactions of substrate (I) with arylboronic acids allow the approac... more Two sequential cross-coupling reactions of substrate (I) with arylboronic acids allow the approach to the desired target compounds.
Products belonging to the pyridopyrimidine family are characterized by their intense use in pharm... more Products belonging to the pyridopyrimidine family are characterized by their intense use in pharmacology. The increase of interest for this heterocyclic scaffold prompted different research teams around the world to study their chemically and biologically properties. In this work, we are interested in the functionalization of pyridopyrimidines and, more specifically, of the less described regioisomer, namely pyrido[3,2-d]pyrimidines. The target compounds were synthesized from 2,7-dichloropyrido[3,2-d]pyrimidine via nucleophilic aromatic substitution and palladium-catalyzed couplings and, in order to obtain potent kinases inhibitors. Our goal has been achieved with several elaborate molecules. These bioactive compounds inhibit kinases such as Cyclin Dependant Kinases (CDK), Glycogen Synthase 3 (GSK3) or Dual specificity tYRosine-phosphorylation-regulated Kinase 1A (DYRK1A) in the nanomolar range. These biological targets are mainly involved in degenerative process or down syndrome. These pharmacological results led us to extend our studies to other pyridopyrimidines, namely pyrido[2,3-d]pyrimidines as well as other types of polynitrogenated bicycles, namely imidazo[1,2- a]pyridine and imidazo[1,2-b]pyridazine.
Polycyclic Aromatic Compounds, Apr 19, 2022
The hydroxyapatite nanoparticles (HANPs) were prepared by microwave assisted coprecipitation meth... more The hydroxyapatite nanoparticles (HANPs) were prepared by microwave assisted coprecipitation method and assessed their efficacy on flocculation of microalga, Chlorella vulgaris. The co-precipitation was initiated by mixing the Ca(OH) 2 and H 3 PO 4 and allowed 2 them to form the HANPs through exposure of microwave irradiation at 10 min (HA1) and 15 min (HA2). In which the 15 min (HA2) exposure showed the better and stable formation of the HANPs. The results showed the both HANPs was found to be needle-shaped and size from 15 to 50 nm evident by TEM analysis and its crystallinity was confirmed by XRD analysis. The addition of 300 mg. mL-1 of HA2 enhanced the flocculation of C. vulgaris with the efficiency of 90% in 60 min. Hence, this work proposed that use of HANPs in flocculation procedures is a more promising and cost-effective method for microalgal biomass harvesting.
Journal of Molecular Structure, Oct 1, 2022
HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific re... more HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.
Synlett, Sep 13, 2012
Regioselective syntheses of 1,4,5-trisubstituted 1,2,3-triazoles were accomplished by three diffe... more Regioselective syntheses of 1,4,5-trisubstituted 1,2,3-triazoles were accomplished by three different strategies, relying on (i) the interception of stoichiometrically formed 5-cuprated-1,2,3-triazoles, (ii) the use of stoichiometrically functionalized alkynes or (iii) catalytic C-H bond functionalizations. This perspective article summarizes progress in this research area until June 2010.
Polycyclic Aromatic Compounds
Les produits appartenant à la famille des pyridopyrimidines sont caractérisés par leur intense ut... more Les produits appartenant à la famille des pyridopyrimidines sont caractérisés par leur intense utilisation dans le domaine pharmacologique, ce qui a poussé différentes équipes de recherche, de par le monde, à les étudier chimiquement et biologiquement. Dans ce travail, nous nous sommes intéressés au groupe des pyridopyrimidines et, plus particulièrement, à l’isomère le moins décrit dans la littérature, à savoir les pyrido[3,2-d]pyrimidines. Les composés ciblés sont synthétisés à partir de la 2,7-dichloropyrido[3,2-d]pyrimidine, via des substitutions nucléophiles aromatiques et des couplages pallado-catalysés et ce, dans le but d’obtenir de puissants inhibiteurs de kinases. Ce but a été atteint puisqu’en effet plusieurs des molécules élaborées inhibent les kinases testées avec des concentrations de l’ordre du nanomolaire. Des résultats pharmacologiques aussi concluants nous ont amenés à étendre nos études à d’autres pyridopyrimidines, à savoir les pyrido[2,3-d]pyrimidines ainsi qu’à ...
Journal of Molecular Structure
HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific re... more HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.
An efficient synthesis of 1,3-oxazine and 1,3-thiazine derivatives has been demonstrated through ... more An efficient synthesis of 1,3-oxazine and 1,3-thiazine derivatives has been demonstrated through a one-pot multicomponent condensation reaction (MCR). Urea and thiourea have been used as reagent and catalyst system for this reaction. The method produced good to excellent product yields. The synthesized compounds were evaluated for their antibacterial and antifungal activities in vitro against four bacteria and two fungi.
Products belonging to the pyridopyrimidine family are characterized by their intense use in pharm... more Products belonging to the pyridopyrimidine family are characterized by their intense use in pharmacology. The increase of interest for this heterocyclic scaffold prompted different research teams around the world to study their chemically and biologically properties. In this work, we are interested in the functionalization of pyridopyrimidines and, more specifically, of the less described regioisomer, namely pyrido[3,2-d]pyrimidines. The target compounds were synthesized from 2,7-dichloropyrido[3,2-d]pyrimidine via nucleophilic aromatic substitution and palladium-catalyzed couplings and, in order to obtain potent kinases inhibitors. Our goal has been achieved with several elaborate molecules. These bioactive compounds inhibit kinases such as Cyclin Dependant Kinases (CDK), Glycogen Synthase 3 (GSK3) or Dual specificity tYRosine-phosphorylation-regulated Kinase 1A (DYRK1A) in the nanomolar range. These biological targets are mainly involved in degenerative process or down syndrome. T...
The present invention relates to a compound of the following general formula (I): embedded image ... more The present invention relates to a compound of the following general formula (I): embedded image in which: R 1 is in particular H, a halogen atom or an aryl group; R 2 is in particular a halogen atom or an aryl group, R 3 is in particular a halogen atom or an aryl or heteroaryl group, as well as its pharmaceutically acceptable salts, its hydrates or its polymorphic crystalline structures, its racemates, diastereoisomers or enantiomers.
Polycyclic Aromatic Compounds, 2021
Journal of Environmental Chemical Engineering, 2021
Abstract Solvents and catalysts are among the key factors in achieving the green chemical synthes... more Abstract Solvents and catalysts are among the key factors in achieving the green chemical synthesis of bioactive compounds. In this regard, metal-doped nanoparticles, as a heterogeneous catalyst, in urea-based deep eutectic mixtures were used to prepare a series of pyrrolidinone-substituted benzothiazoles. In the strategy developed herein, pyrrolidinone derivatives were synthesized by reacting different arylamines with dimethyl itaconate using water as the solvent in a microwave. Then, the as-obtained pyrrolidinone derivatives were reacted with 2-aminothiophenol under microwave irradiation with the assistance of a deep eutectic mixture (CuCl2 or NiCl2/urea) and Cu- or Ni-doped TiO2 nanoparticles to afford the final derivative incorporating both pyrrolidin-2-one and benzothiazole rings. To determine the optimum reaction conditions, the effect of temperature, solvent nature, and reaction time was investigated. Under the optimal operation conditions, high reaction yields were achieved. The developed strategy exhibited advantages of a short reaction time, eco-friendliness, and high productivity. Finally, the obtained derivatives were examined in terms of their antibacterial potential against selected Gram-negative and Gram-positive bacterial strains: Eight of the derivatives exhibited activity against the tested bacteria.
Materials Chemistry and Physics, 2021
• Copper and nickel single-doped TiO 2 nanostructures were successfully prepared. • Structures, e... more • Copper and nickel single-doped TiO 2 nanostructures were successfully prepared. • Structures, elemental compositions and morphologies were characterized. • The catalytic performance of the Cu-doped and Ni-doped TiO 2 nanostructures were evaluated. • The pyridopyrimidine derivatives was prepared using doped TiO 2 nanostructures.
Green Chemistry Letters and Reviews, 2018
An efficient and ecofriendly method for the synthesis of disubstituted 5-aminopyrimidines from vi... more An efficient and ecofriendly method for the synthesis of disubstituted 5-aminopyrimidines from vinyl azides and urea or thiourea was developed. This reaction proceeds under microwave irradiation conditions in the presence of water as a solvent. The remarkable features of this new protocol are high conversion, short reaction times, cleaner reaction profiles and straightforward procedure.
Current Organic Chemistry, 2018
Green Chemistry Letters and Reviews, 2018
An eco-friendly and efficient method was developed for the preparation of a new series of sulfurc... more An eco-friendly and efficient method was developed for the preparation of a new series of sulfurcontaining quinolinthiones. Compounds 6a-o were synthesized from 4-methyl-2-thiocoumarin and arylhydrazides using water as a solvent under microwave irradiation. Some noteworthy features of our novel method are its cleanliness, short reaction time and high conversion rate, and the reaction proceeds (profiles) using a simple procedure. All of the prepared compounds were screened for their antibacterial efficacy in vitro using the disc diffusion method against bacterial strains. Compound (6j) showed the greatest potency with a 16 and 19 mm inhibition zone against Klebsiella pneumonia and Staphylococcus aureus, respectively.
Green Chemistry Letters and Reviews, 2017
Animal-bone-meal-supported palladium (0) was prepared and used as catalyst in the Suzuki coupling... more Animal-bone-meal-supported palladium (0) was prepared and used as catalyst in the Suzuki coupling reaction in water, under sunlight as an alternative source of energy. This palladium has showed a high catalytic activity than tetrakis(triphenylphosphine) palladium (Pd(PPh 3) 4) in the Suzuki cross-coupling reaction (the reaction of 4-halogenopyridopyrimidine with boronic acids) in water via sunlight as the light source, with no addition of ligands. This green method affords heteroaryls with excellent yields in comparison with the classical method using tetrakis (triphenylphosphine) palladium. The green catalyst did not show any significant loss of activity, even when used up to five times.