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Auteur Ali Belfaitah |
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Titre : Les dérivés poly-hétérocycliques : les halogénoimidazoles et benzimidazole-hétérocycles : synthèse, réactivité et evaluation biologique Type de document : texte imprimé Auteurs : Sana Zama, Auteur ; Ali Belfaitah, Directeur de thèse Editeur : جامعة الإخوة منتوري قسنطينة Année de publication : 2015 Importance : 221 f. Format : 30 cm. Note générale : 2 copies imprimées disponibles
Langues : Français (fre) Catégories : Français - Anglais
ChimieTags : imidazole, halogénation, benzimidazole, N-méthylation, réaction d’additionhétérocyclisation, poly-hétérocycles, activité biologique
imidazole, halogenation, benzimidazole, addition-heterocyclisation reaction, polyheterocycles, Tacrine, biological activity.
إيميدازول، الهلجنة ، النترتة، أملاح الإيميدازوليوم ، النشاطر المضاد للجراثيم ، بنزيميدازول، التاكرينIndex. décimale : 540 Chimie et sciences connexes Résumé : A number of halo-1 -methyl-1 H-imidazole derivatives as basis materials such as 2-bromo-1 - methylimidazole (3), 2-bromo-5-nitro-1 -methylimidazole (6), 2,4,5-tribromoimidazole (7), and 4,5- dibromo(diiodo)-N-alkyl-1 -méthylimidazoles differently substituted at position 2 (8a-d), were prepared using various and appropriate methods as halogenation reaction (bromination and iodination), nitration, N-alkylation, and selective bromination.
A quaternization reaction allowed us to prepare a variety of imidazolium salts carriers an electron-withdrawing group on the quaternary nitrogen, such as bromides of 4,5-dibromo (diiodo)-1 - methyl-1 H-imidazolium (16a-d), and a range of 2-bromo-1 -methyl-1 H-imidazolium bromide (17a-g), using as starting material 2-bromo-1 -methyl-1 H-imidazole. No evolution of the reaction was observed
during the quaternization reaction of 2-bromo-5-nitro-1 -methyl-1 H-imidazole (6).The reactivity of these imidazolium salts has been then studied.
The addition of CS2 in the presence of Et3Nt o the 4,5-dihalo-1 -methyl-1 H-imidazolium salts in acetonitrile ordioxane, shows no progress of the reaction, recovering the starting material as amajor product.The same procedure applied to 2-bromo-1 -methyl-1 H-imidazolium salts (CS2/Et3N, CH3CN, 25 °C) was successful and resulted in the synthesis of a series oforiginalbi-cyclic meso-ionic compounds: thethiazolo[3,2-a]imidazoles (18a-h),while the addition of KSCN in the presence of Et3N leads to a product corresponding to the substitution of the bromine at the 2-position by sulfur,the 2-(1 - méthyl-2-thio-1,2-dihydroimidazol-3-yl)-1 -aryléthanone (19a-b). Addition of arylamine provides the corresponding 2-arylamino-1 -methyl-1 H-imidazolium bromide (20a-e) along as econd minor product
(<10%) identified to the N-phenacyl-2-imidazolone (21).
Similarly, several series of highly functionalized poly-substituted imidazole derivatives (22a-f, 23a-c, 24a-c, 25a-cand26a-c) were prepared by N-alkylation reaction of 4,5-dihalo-1 -methyl-1 Himidazoles, and then subjected to evaluation of their antimicrobial activity.
A variety of original poly-heterocyclic compounds as 1 -methyl-1 H-benzo[d]imidazole
derivatives associated at 2-position with highlyunctionalized heterocycles such as 4H-pyrans (31-33), chromene (34), benzochromenes (35-36), 1,4-dihydropyridines (38-39), quinazolines (40-41), pyridines(42a-c), and pyrrolidines (44-45) were prepared from 1 -methyl-1 H-benzo[d]imidazole-2- carbaldehyde (29) using adequate and appropriate methods. Similarly, the preparation of structural analogues of Tacrine (a drug used in the treatment of Alzheimer's disease) has been explored, and three hybrid benzimidazole-tacrine compounds (46-48) have been prepared.
Yields are good in most cases. All prepared compounds were identified by usual spectroscopic methods (IR, 1H NMR and13C), and for some of them additional analyzes were carried out (X-ray diffraction, and/or elemental analysis).Diplôme : Doctorat En ligne : ../theses/chimie/ZAM6822.pdf Format de la ressource électronique : Permalink : https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=10092 Les dérivés poly-hétérocycliques : les halogénoimidazoles et benzimidazole-hétérocycles : synthèse, réactivité et evaluation biologique [texte imprimé] / Sana Zama, Auteur ; Ali Belfaitah, Directeur de thèse . - جامعة الإخوة منتوري قسنطينة, 2015 . - 221 f. ; 30 cm.
2 copies imprimées disponibles
Langues : Français (fre)
Catégories : Français - Anglais
ChimieTags : imidazole, halogénation, benzimidazole, N-méthylation, réaction d’additionhétérocyclisation, poly-hétérocycles, activité biologique
imidazole, halogenation, benzimidazole, addition-heterocyclisation reaction, polyheterocycles, Tacrine, biological activity.
إيميدازول، الهلجنة ، النترتة، أملاح الإيميدازوليوم ، النشاطر المضاد للجراثيم ، بنزيميدازول، التاكرينIndex. décimale : 540 Chimie et sciences connexes Résumé : A number of halo-1 -methyl-1 H-imidazole derivatives as basis materials such as 2-bromo-1 - methylimidazole (3), 2-bromo-5-nitro-1 -methylimidazole (6), 2,4,5-tribromoimidazole (7), and 4,5- dibromo(diiodo)-N-alkyl-1 -méthylimidazoles differently substituted at position 2 (8a-d), were prepared using various and appropriate methods as halogenation reaction (bromination and iodination), nitration, N-alkylation, and selective bromination.
A quaternization reaction allowed us to prepare a variety of imidazolium salts carriers an electron-withdrawing group on the quaternary nitrogen, such as bromides of 4,5-dibromo (diiodo)-1 - methyl-1 H-imidazolium (16a-d), and a range of 2-bromo-1 -methyl-1 H-imidazolium bromide (17a-g), using as starting material 2-bromo-1 -methyl-1 H-imidazole. No evolution of the reaction was observed
during the quaternization reaction of 2-bromo-5-nitro-1 -methyl-1 H-imidazole (6).The reactivity of these imidazolium salts has been then studied.
The addition of CS2 in the presence of Et3Nt o the 4,5-dihalo-1 -methyl-1 H-imidazolium salts in acetonitrile ordioxane, shows no progress of the reaction, recovering the starting material as amajor product.The same procedure applied to 2-bromo-1 -methyl-1 H-imidazolium salts (CS2/Et3N, CH3CN, 25 °C) was successful and resulted in the synthesis of a series oforiginalbi-cyclic meso-ionic compounds: thethiazolo[3,2-a]imidazoles (18a-h),while the addition of KSCN in the presence of Et3N leads to a product corresponding to the substitution of the bromine at the 2-position by sulfur,the 2-(1 - méthyl-2-thio-1,2-dihydroimidazol-3-yl)-1 -aryléthanone (19a-b). Addition of arylamine provides the corresponding 2-arylamino-1 -methyl-1 H-imidazolium bromide (20a-e) along as econd minor product
(<10%) identified to the N-phenacyl-2-imidazolone (21).
Similarly, several series of highly functionalized poly-substituted imidazole derivatives (22a-f, 23a-c, 24a-c, 25a-cand26a-c) were prepared by N-alkylation reaction of 4,5-dihalo-1 -methyl-1 Himidazoles, and then subjected to evaluation of their antimicrobial activity.
A variety of original poly-heterocyclic compounds as 1 -methyl-1 H-benzo[d]imidazole
derivatives associated at 2-position with highlyunctionalized heterocycles such as 4H-pyrans (31-33), chromene (34), benzochromenes (35-36), 1,4-dihydropyridines (38-39), quinazolines (40-41), pyridines(42a-c), and pyrrolidines (44-45) were prepared from 1 -methyl-1 H-benzo[d]imidazole-2- carbaldehyde (29) using adequate and appropriate methods. Similarly, the preparation of structural analogues of Tacrine (a drug used in the treatment of Alzheimer's disease) has been explored, and three hybrid benzimidazole-tacrine compounds (46-48) have been prepared.
Yields are good in most cases. All prepared compounds were identified by usual spectroscopic methods (IR, 1H NMR and13C), and for some of them additional analyzes were carried out (X-ray diffraction, and/or elemental analysis).Diplôme : Doctorat En ligne : ../theses/chimie/ZAM6822.pdf Format de la ressource électronique : Permalink : https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=10092 Exemplaires (1)
Code-barres Cote Support Localisation Section Disponibilité ZAM/6822 ZAM/6822 Thèse Bibliothèque principale Thèses Disponible Les liquides ioniques dans la réaction d’hétéro-cyclisation intramoléculaire de 2-aminochalcones et 2-époxychalcones / Meryem Chelghoum
Titre : Les liquides ioniques dans la réaction d’hétéro-cyclisation intramoléculaire de 2-aminochalcones et 2-époxychalcones : Synthése et évaluation biologique de dérivés de l’imidazole quaternairisés hautement fonctionnalisés. Type de document : texte imprimé Auteurs : Meryem Chelghoum, Auteur ; Ali Belfaitah, Directeur de thèse Editeur : جامعة الإخوة منتوري قسنطينة Année de publication : 2018 Importance : 165 f. Format : 30 cm. Note générale : Doctorat 3éme CYCLE LMD.
2 copies imprimées disponibles
Langues : Français (fre) Catégories : Français - Anglais
ChimieTags : Chimie: chimie organique Liquides ioniques Aza-analogues de flavonoïdes Cyclisation intramoléculaire Imidazole O834 Fonctionnalisation Sels d’imidazolium Activité biologique ionic liquid intramolecular hetero-cyclization imidazolium salt antibacterial activity سوائل أيونية مشابهات الفلافونويدات تفاعل حرلقي داخل الجزيء ايميدازول املاح ايميدازول نشاط البيولوجي Index. décimale : 540 Chimie et sciences connexes Résumé :
Two distinct themes were discussed during this thesis. The first concerns the synthesis and the use of ionic liquids in the intramolecular hetero-cyclization reaction of 2-aminochalcones and 1,2-epoxy-2-aminochalcones, while the second relates to the preparation and evaluation of antibacterial activity of quaternized poly-functionalized imidazolium salts. In the first part dedicated (reserved) to the isomerization reaction of 2-aminochalcones and 2- aminochalcones epoxides in ionic liquid environment, we have shown that the reaction proceeds correctly, and it is applicable to a wide range of substrates, without the use of an additional catalyst. the cyclization of The derivatives of (E) -1- (2-aminophenyl) -3-phenylpropen-2- en-1-one were tested in Three ionic liquids [bPy] [BF4], [bmim] [BF4] and [bmim] [PF6], among these [bmim] [BF4] is the most efficient (ratio LI / substrate: 10/1, temperature: 150 ° C, reaction time: 2.5 h). The 2-aryl-2,3-dihydroquinolin-4 (1H) -ones have been obtained with satisfactory yields (70-92%) in ionic liquid [bmim] [BF4], the (this) latter is recyclable three times with a slight decrease in its catalytic activity (83 → 64%). We also reported a practical and effective protocol for the synthesis of 2-aryl-3-hydroxy-1,2,3,4- tetrahydroquinolin-4 (1H) -ones by an intramolecular cyclization reaction of epoxyde 2- aminochalcone in ionic liquid at 120 ° C (LI ratio / substrate: 5/1, temperature: 120 ° C, reaction time: 6 h) of the four ionic liquids investigated, [bmim] [OTf] gave the best results in terms of cyclized product yield (35-93%). The structures of the compounds prepared were elucidated by the usual spectroscopic methods (IR, 1H NMR and C-13), and other elemental analysis and Xray diffraction for some of them. In the second part, a whole series of highly functionalized imidazolium salt derivatives were prepared (12 compounds) and their structures elucidated by the usual spectroscopic methods (IR, 1H NMR and C-13) and by X-ray diffraction for some of them. Most of these compounds were evaluated for their inhibitory capacity against four pathogenic strains: three Gramnegative (Escherichia coli, Salmonella thipymurium and Pseudomonas aeruginosa) and one Gram-positive (Staphylococcus aureus) using two methods: the inhibition zone and the determination of the minimum inhibitory concentration (MIC). The MIC results shows that iodine derivatives have inhibitory activity against Gram-negative strains, superior to brominated derivatives and compounds bearing a nitro group. Staphylococcus aureus (Grampositive bacteria) are significantly less sensitive to the action of the substrates used.
Note de contenu :
Annexes.Diplôme : Doctorat En ligne : ../theses/chimie/CHE7406.pdf Format de la ressource électronique : Permalink : https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=11058 Les liquides ioniques dans la réaction d’hétéro-cyclisation intramoléculaire de 2-aminochalcones et 2-époxychalcones : Synthése et évaluation biologique de dérivés de l’imidazole quaternairisés hautement fonctionnalisés. [texte imprimé] / Meryem Chelghoum, Auteur ; Ali Belfaitah, Directeur de thèse . - جامعة الإخوة منتوري قسنطينة, 2018 . - 165 f. ; 30 cm.
Doctorat 3éme CYCLE LMD.
2 copies imprimées disponibles
Langues : Français (fre)
Catégories : Français - Anglais
ChimieTags : Chimie: chimie organique Liquides ioniques Aza-analogues de flavonoïdes Cyclisation intramoléculaire Imidazole O834 Fonctionnalisation Sels d’imidazolium Activité biologique ionic liquid intramolecular hetero-cyclization imidazolium salt antibacterial activity سوائل أيونية مشابهات الفلافونويدات تفاعل حرلقي داخل الجزيء ايميدازول املاح ايميدازول نشاط البيولوجي Index. décimale : 540 Chimie et sciences connexes Résumé :
Two distinct themes were discussed during this thesis. The first concerns the synthesis and the use of ionic liquids in the intramolecular hetero-cyclization reaction of 2-aminochalcones and 1,2-epoxy-2-aminochalcones, while the second relates to the preparation and evaluation of antibacterial activity of quaternized poly-functionalized imidazolium salts. In the first part dedicated (reserved) to the isomerization reaction of 2-aminochalcones and 2- aminochalcones epoxides in ionic liquid environment, we have shown that the reaction proceeds correctly, and it is applicable to a wide range of substrates, without the use of an additional catalyst. the cyclization of The derivatives of (E) -1- (2-aminophenyl) -3-phenylpropen-2- en-1-one were tested in Three ionic liquids [bPy] [BF4], [bmim] [BF4] and [bmim] [PF6], among these [bmim] [BF4] is the most efficient (ratio LI / substrate: 10/1, temperature: 150 ° C, reaction time: 2.5 h). The 2-aryl-2,3-dihydroquinolin-4 (1H) -ones have been obtained with satisfactory yields (70-92%) in ionic liquid [bmim] [BF4], the (this) latter is recyclable three times with a slight decrease in its catalytic activity (83 → 64%). We also reported a practical and effective protocol for the synthesis of 2-aryl-3-hydroxy-1,2,3,4- tetrahydroquinolin-4 (1H) -ones by an intramolecular cyclization reaction of epoxyde 2- aminochalcone in ionic liquid at 120 ° C (LI ratio / substrate: 5/1, temperature: 120 ° C, reaction time: 6 h) of the four ionic liquids investigated, [bmim] [OTf] gave the best results in terms of cyclized product yield (35-93%). The structures of the compounds prepared were elucidated by the usual spectroscopic methods (IR, 1H NMR and C-13), and other elemental analysis and Xray diffraction for some of them. In the second part, a whole series of highly functionalized imidazolium salt derivatives were prepared (12 compounds) and their structures elucidated by the usual spectroscopic methods (IR, 1H NMR and C-13) and by X-ray diffraction for some of them. Most of these compounds were evaluated for their inhibitory capacity against four pathogenic strains: three Gramnegative (Escherichia coli, Salmonella thipymurium and Pseudomonas aeruginosa) and one Gram-positive (Staphylococcus aureus) using two methods: the inhibition zone and the determination of the minimum inhibitory concentration (MIC). The MIC results shows that iodine derivatives have inhibitory activity against Gram-negative strains, superior to brominated derivatives and compounds bearing a nitro group. Staphylococcus aureus (Grampositive bacteria) are significantly less sensitive to the action of the substrates used.
Note de contenu :
Annexes.Diplôme : Doctorat En ligne : ../theses/chimie/CHE7406.pdf Format de la ressource électronique : Permalink : https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=11058 Exemplaires (1)
Code-barres Cote Support Localisation Section Disponibilité CHE/7406 CHE/7406 Thèse Bibliothèque principale Thèses Disponible
Titre : Préparation et évaluation biologique de composés polycycliques hybrides quinoléine-hétérocycles à visée thérapeutique Type de document : texte imprimé Auteurs : Hasna Haiour, Auteur ; Ali Belfaitah, Directeur de thèse Editeur : Constantine : Université Mentouri Constantine Année de publication : 2015 Importance : 182 f. Format : 30 cm. Note générale : 2 copies imprimées disponibles
Langues : Français (fre) Catégories : Français - Anglais
ChimieTags : Quinoléine réaction d’addition-hétéro-cyclisation hybride quinoléine-hétérocycle Maladie ’Alzheimer Tacrine activité biologique "Quinoline, addition-heterocyclisation reaction poly-heterocyclic compounds Alzheimer's disease Tacrine’s analog biological activity كينولين تفاعلات الاضافة مشتقات الكينولين ذات الحلقات غير التجانسة مرض ألزهايمر تاكرين فعالية بيولوجية Index. décimale : 540 Chimie et sciences connexes Résumé : A number of original hybrids as (2-chloroquinolin-3-yl)-heterocyclic compounds were prepared from differently substituted 2-chloroquinolin-3-carbaldehydes. A series of4H-pyrans derivatives carriers an ester or ketone (aliphatic and cyclic), a nitrile and an amine functions linked in position 4 with variously substituted(2-chloroquinolin-3-yl) patterns (4a-4i) were prepared in very good yields (82-92%). Two series of (2-chloroquinolin-3-yl)-pyridine hybrids such as 2-amino-4-(2-chloroquinolin-3-yl)-6-substituted-nicotinonitriles (compounds
13-20), and 2-amino-4-(2-chloroquinolin-3-yl)-5,6,7,8-tetrahydroquinolin-3-carbonitrile derivatives (21-24) were prepared in variable yields (24-46%) from 3-(2-chloro-quinolin-3- yl)-2-cyanoacrylonitriles (3a-3d) as key intermediates in moderate yields (43-47%).
The same approach was used to access to new highly functionalized (quinolin-6-yl)- heterocycles with various structures such as (quinolin-6-yl)-4H-pyran (32a-b, 33a et 34a-b), - 2-aminobenzochromene (35 et 36), and -1,4-dihydropyridine (compound 37), and that from a single intermediate the ethyl 2-chloro-6-formylquinolin-3-carboxylate (30). Yields are relatively low (10-20%) to acceptable (41-58%).
A ""recovery"" hybrid derivatives (quinoline-3-yl)-4H-pyran was undertaken and resulted in the preparation of some series of highly original and diversely functionalized structural analogues of Tacrine (a bioactive compound used in the treatment of Alzheimer's disease).
These pyranotacrines (quinolin-3-yl)-4H-pyran-tacrine) carriers in position 5 of 4H-pyran ring an electron-withdrawing group (series 5, 6, 7, 8; and compounds 9-12) were prepared under the standard conditions of the Friedländer’s reaction in satisfactory yields for most (39- 70%). The same conditions apply to (2-chloroquinolin-3-yl)-pyridine derivatives (13-20) do not appear altered these substrates (no evolution of the reaction).
The in vitro biological evaluation (anti-Alzheimer's tests) of products of series 5,6,7, and compounds 9-12 as the determination of hepatotoxicity, measurement of inhibitory power toward acetylcholinesterase, butyrylcholinesterase, and induced aggregation of -amyloïd A1-40, neuroprotection and neurotoxicity, have shown that these new pyranotacrines are multipotent, non-hepatotoxic, non competitive acetylcholinesterase inhibitors, A1-40 antiaggregants, neuroprotective, and non-neurotoxic agents for Alzheimer’s disease.
All prepared compounds were identified by usual spectroscopic methods (IR, 1H NMR and13C), and for some of them additional analyzes were carried out (X-ray diffraction, elemental analysis, MS and/or HRMS).
Diplôme : Doctorat En ligne : ../theses/chimie/HAI6748.pdf Format de la ressource électronique : Permalink : https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=9867 Préparation et évaluation biologique de composés polycycliques hybrides quinoléine-hétérocycles à visée thérapeutique [texte imprimé] / Hasna Haiour, Auteur ; Ali Belfaitah, Directeur de thèse . - Constantine : Université Mentouri Constantine, 2015 . - 182 f. ; 30 cm.
2 copies imprimées disponibles
Langues : Français (fre)
Catégories : Français - Anglais
ChimieTags : Quinoléine réaction d’addition-hétéro-cyclisation hybride quinoléine-hétérocycle Maladie ’Alzheimer Tacrine activité biologique "Quinoline, addition-heterocyclisation reaction poly-heterocyclic compounds Alzheimer's disease Tacrine’s analog biological activity كينولين تفاعلات الاضافة مشتقات الكينولين ذات الحلقات غير التجانسة مرض ألزهايمر تاكرين فعالية بيولوجية Index. décimale : 540 Chimie et sciences connexes Résumé : A number of original hybrids as (2-chloroquinolin-3-yl)-heterocyclic compounds were prepared from differently substituted 2-chloroquinolin-3-carbaldehydes. A series of4H-pyrans derivatives carriers an ester or ketone (aliphatic and cyclic), a nitrile and an amine functions linked in position 4 with variously substituted(2-chloroquinolin-3-yl) patterns (4a-4i) were prepared in very good yields (82-92%). Two series of (2-chloroquinolin-3-yl)-pyridine hybrids such as 2-amino-4-(2-chloroquinolin-3-yl)-6-substituted-nicotinonitriles (compounds
13-20), and 2-amino-4-(2-chloroquinolin-3-yl)-5,6,7,8-tetrahydroquinolin-3-carbonitrile derivatives (21-24) were prepared in variable yields (24-46%) from 3-(2-chloro-quinolin-3- yl)-2-cyanoacrylonitriles (3a-3d) as key intermediates in moderate yields (43-47%).
The same approach was used to access to new highly functionalized (quinolin-6-yl)- heterocycles with various structures such as (quinolin-6-yl)-4H-pyran (32a-b, 33a et 34a-b), - 2-aminobenzochromene (35 et 36), and -1,4-dihydropyridine (compound 37), and that from a single intermediate the ethyl 2-chloro-6-formylquinolin-3-carboxylate (30). Yields are relatively low (10-20%) to acceptable (41-58%).
A ""recovery"" hybrid derivatives (quinoline-3-yl)-4H-pyran was undertaken and resulted in the preparation of some series of highly original and diversely functionalized structural analogues of Tacrine (a bioactive compound used in the treatment of Alzheimer's disease).
These pyranotacrines (quinolin-3-yl)-4H-pyran-tacrine) carriers in position 5 of 4H-pyran ring an electron-withdrawing group (series 5, 6, 7, 8; and compounds 9-12) were prepared under the standard conditions of the Friedländer’s reaction in satisfactory yields for most (39- 70%). The same conditions apply to (2-chloroquinolin-3-yl)-pyridine derivatives (13-20) do not appear altered these substrates (no evolution of the reaction).
The in vitro biological evaluation (anti-Alzheimer's tests) of products of series 5,6,7, and compounds 9-12 as the determination of hepatotoxicity, measurement of inhibitory power toward acetylcholinesterase, butyrylcholinesterase, and induced aggregation of -amyloïd A1-40, neuroprotection and neurotoxicity, have shown that these new pyranotacrines are multipotent, non-hepatotoxic, non competitive acetylcholinesterase inhibitors, A1-40 antiaggregants, neuroprotective, and non-neurotoxic agents for Alzheimer’s disease.
All prepared compounds were identified by usual spectroscopic methods (IR, 1H NMR and13C), and for some of them additional analyzes were carried out (X-ray diffraction, elemental analysis, MS and/or HRMS).
Diplôme : Doctorat En ligne : ../theses/chimie/HAI6748.pdf Format de la ressource électronique : Permalink : https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=9867 Exemplaires (1)
Code-barres Cote Support Localisation Section Disponibilité HAI/6748 HAI/6748 Thèse Bibliothèque principale Thèses Disponible
Titre : Préparation de nouveaux matériaux à base de (benz)imidazole et bio-activité : synthèse de complexes à base de (benz)imidazole, étude structurale et théorique et préparation d’analogues structuraux de la Tacrine à base de benzimidazole. Type de document : texte imprimé Auteurs : Anfel Benhassine ép Lifa, Auteur ; Ali Belfaitah, Directeur de thèse Editeur : جامعة الإخوة منتوري قسنطينة Année de publication : 2018 Importance : 186 f. Format : 30 cm. Note générale : 2 copies imprimées disponibles
Langues : Français (fre) Catégories : Français - Anglais
ChimieTags : Imidazole Benzimidazole Complexassion Métaux de transition divalents DFT orbitales frontières Tacrine réaction de Friedländer poly-hétérocycles DPPH ABTS activité antimicrobienne Divalent transition metals calculations Frontier orbitals Friedländer's reaction poly-heterocyclic compounds antimicrobial activity إيميدازول بنزيميدازول المعقدات المعادن الانتقالية ثنائية التكافؤ النشاط المضاد للأكسدة التاكرين البنزوبرانوتاكرين النشاط المضاد للميكروبات Index. décimale : 540 Chimie et sciences connexes Résumé : The first part, which is subdivided into two chapters, concerns the synthesis, characterization (IR and UV-Vis, X-ray diffraction, and other elemental analysis) and biological evaluation of divalent transition metal complexes (M = Co , Cu, Cd, Zn, Ni) based on (1-methyl- 1Hbenzo[d]imidazol-2-yl) methanol (L1/Hmbm) (complexes 1-4) and (1-methyl-1H- imidazol-2-yl) methanol (L2/Hmim) (complexes 5-11). In both series of coordination compounds, the ligand (L1 or L2) gives rise to a variety of metal-ligand coordination modes(monodentate or bidentadate) exhibiting tetrahedral or octahedral geometry.The in vitro measurement of the antioxidant activity of the L1 and L2 ligands and their respective metal complexes against the free radical scavenger DPPH at low concentration (100 &g / mL), showed a moderate to significant antioxidant activities, compared to the standard (Asc). The complexes (5-11) and the ligand L2 were submitted to an in vitro evaluation of their antimicrobial activity against five pathogenic strains: animal bacteria:
Gram (+) (S. aureus) and Gram (-) (K pneumonia), a Gram (+) phytopathogenic bacterium (P.
syringae), a yeast (P. caribbica) and a fungus (Trichodermsp), using the disk diffusion method
(agar).The analysis of the results revealed a significant difference in the inhibition profile of the selected strains. The complex 5 and to a lesser extent the complex 6, gave the best results displaying significant inhibitory activities on mostly all pathogenic strains (broad spectrum). In the second part dedicated to the synthesis of structural analogs of Tacrine, a whole series of new poly-heterocyclic compounds (10-14) was prepared from the corresponding 4H-pyrans (5- 9) by an addition-hetero-cyclization reaction of cyclohexanone under the Friedl‰ndler's standard conditions reaction. The in vitro antioxidant tests (DPPH and ABTS) of
benzimidazopyranotacrines, showed that the five compounds have an antioxidant activities, and
the 5-Amino-2-methyl-4-(1-methyl-1H-benzo[d]imidazol-2-yl)-6,7,8,9-tetrahydro-4H-pyrano
[2,3-b]uinolin-3-yl) ethanone (compound 12) is the most efficient, exhibiting a comparable
inhibitory power of free radicals to that of reference compounds (controls). The structure of all the complexes (1-11) was determined by X-ray diffraction, IR, UV and other elemental analysis. For complexes 1-4, theoretical studies using DFT and TD-DFT calculations have been performed and confirmed the experimental results. Benzimidazopyranotacrines (10-14) as structural Tacrine's analogues and their intermediates 4Hpyrans (5-9), were identified by the usual spectroscopic methods (IR, 1H NMR and13C).Diplôme : Doctorat En ligne : ../theses/chimie/LIF7359.pdf Format de la ressource électronique : Permalink : https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=11008 Préparation de nouveaux matériaux à base de (benz)imidazole et bio-activité : synthèse de complexes à base de (benz)imidazole, étude structurale et théorique et préparation d’analogues structuraux de la Tacrine à base de benzimidazole. [texte imprimé] / Anfel Benhassine ép Lifa, Auteur ; Ali Belfaitah, Directeur de thèse . - جامعة الإخوة منتوري قسنطينة, 2018 . - 186 f. ; 30 cm.
2 copies imprimées disponibles
Langues : Français (fre)
Catégories : Français - Anglais
ChimieTags : Imidazole Benzimidazole Complexassion Métaux de transition divalents DFT orbitales frontières Tacrine réaction de Friedländer poly-hétérocycles DPPH ABTS activité antimicrobienne Divalent transition metals calculations Frontier orbitals Friedländer's reaction poly-heterocyclic compounds antimicrobial activity إيميدازول بنزيميدازول المعقدات المعادن الانتقالية ثنائية التكافؤ النشاط المضاد للأكسدة التاكرين البنزوبرانوتاكرين النشاط المضاد للميكروبات Index. décimale : 540 Chimie et sciences connexes Résumé : The first part, which is subdivided into two chapters, concerns the synthesis, characterization (IR and UV-Vis, X-ray diffraction, and other elemental analysis) and biological evaluation of divalent transition metal complexes (M = Co , Cu, Cd, Zn, Ni) based on (1-methyl- 1Hbenzo[d]imidazol-2-yl) methanol (L1/Hmbm) (complexes 1-4) and (1-methyl-1H- imidazol-2-yl) methanol (L2/Hmim) (complexes 5-11). In both series of coordination compounds, the ligand (L1 or L2) gives rise to a variety of metal-ligand coordination modes(monodentate or bidentadate) exhibiting tetrahedral or octahedral geometry.The in vitro measurement of the antioxidant activity of the L1 and L2 ligands and their respective metal complexes against the free radical scavenger DPPH at low concentration (100 &g / mL), showed a moderate to significant antioxidant activities, compared to the standard (Asc). The complexes (5-11) and the ligand L2 were submitted to an in vitro evaluation of their antimicrobial activity against five pathogenic strains: animal bacteria:
Gram (+) (S. aureus) and Gram (-) (K pneumonia), a Gram (+) phytopathogenic bacterium (P.
syringae), a yeast (P. caribbica) and a fungus (Trichodermsp), using the disk diffusion method
(agar).The analysis of the results revealed a significant difference in the inhibition profile of the selected strains. The complex 5 and to a lesser extent the complex 6, gave the best results displaying significant inhibitory activities on mostly all pathogenic strains (broad spectrum). In the second part dedicated to the synthesis of structural analogs of Tacrine, a whole series of new poly-heterocyclic compounds (10-14) was prepared from the corresponding 4H-pyrans (5- 9) by an addition-hetero-cyclization reaction of cyclohexanone under the Friedl‰ndler's standard conditions reaction. The in vitro antioxidant tests (DPPH and ABTS) of
benzimidazopyranotacrines, showed that the five compounds have an antioxidant activities, and
the 5-Amino-2-methyl-4-(1-methyl-1H-benzo[d]imidazol-2-yl)-6,7,8,9-tetrahydro-4H-pyrano
[2,3-b]uinolin-3-yl) ethanone (compound 12) is the most efficient, exhibiting a comparable
inhibitory power of free radicals to that of reference compounds (controls). The structure of all the complexes (1-11) was determined by X-ray diffraction, IR, UV and other elemental analysis. For complexes 1-4, theoretical studies using DFT and TD-DFT calculations have been performed and confirmed the experimental results. Benzimidazopyranotacrines (10-14) as structural Tacrine's analogues and their intermediates 4Hpyrans (5-9), were identified by the usual spectroscopic methods (IR, 1H NMR and13C).Diplôme : Doctorat En ligne : ../theses/chimie/LIF7359.pdf Format de la ressource électronique : Permalink : https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=11008 Exemplaires (1)
Code-barres Cote Support Localisation Section Disponibilité LIF/7359 LIF/7359 Thèse Bibliothèque principale Thèses Disponible
Titre : Synthèse, caractérisation et évaluation biologique de nouveaux dérivés poly-hétérocycliques à base d’imidazole Type de document : texte imprimé Auteurs : Houssem Boulebd, Auteur ; Ali Belfaitah, Directeur de thèse Editeur : جامعة الإخوة منتوري قسنطينة Année de publication : 2016 Importance : 257 f. Format : 30 cm. Note générale : 2 copies imprimes disponibles Langues : Français (fre) Catégories : Français - Anglais
ChimieTags : Chimie organique Imidazole halogénation poly-hétérocycles Maladie d’Alzheimer analogues de la
Tacrine hépatotoxicité ORAC activité biologique إيميدازول هلجنة متعدد الحلقات الغير متجانسة مرض الزهايمر نظائرالتاكرين سمية ORACفعالية بيولوجية
Imidazole halogenation poly-heterocyclic compounds Alzheimer's disease
tacrine analogues hepatotoxicity biological activityIndex. décimale : 540 Chimie et sciences connexes Résumé : Some 2-halo-(1-methyl-1H-imidazole) derivatives were prepared by selective halogenation
reaction (bromination, chlorination and iodination). The addition of -bromoacetophenone to
2-bromo(chloro)-1-methyl-1H-imidazole allowed us to access to corresponding imidazolium
salts in satisfactory yields (47-64%). The reactivity of 2-halogeno-N-phenyl-1-methyl-1Himidazolium bromide with activated methylene compounds of diverse structures has been
studied.
A series of original heterocyclic products composed of a core 1-methyl-1H-imidazole
associated at 2-position to highly functionalized heterocyclic compounds such as 4H-pyran,
chromene, benzo (pyrido) chromenes, 1,4-dihydropyridine, pyridine, quinazoline, pyrrolidines
and other pyrazolines have been prepared.
It will be noted that upon addition of methyl ketone derivatives, 1-methylimidazole-pyridine
hybrid compounds obtained are accompanied by the formation of corresponding 2,6-
dicyanoaniline derivatives in low yields. The adaptation of the operating conditions enabled us
to selectively direct the reaction towards the formation of new 2,6-dicyanoaniline derivatives
in good yields for aliphatic methyl ketone derivatives (62-70%), and in 45 % of yield for
acetophenone. These compounds are also fluorescent.
Some series of hybrid compounds such as (1-methyl-1H-imidazol-2-yl)-4H-pyran, -
pyridine, -1,4-dihydropyridine and -quinazoline have been subjected to an in vitro assessment
of their antimicrobial, and antioxydante (DPPH) activities, and also for their hepatotoxicity
towards liver cells HepG2 in a gradient concentration from 1M to 300M, and a structureactivity relationship (SAR) has been demonstrated.
A "valorization" of (1-methyl-1H-imidazol-2-yl)-4-pyran hybrid derivatives was undertaken
and resulted in the preparation of some original series of highly and diversely functionalized
Tacrine analogues (Tacrine is a drug used in the treatment of Alzheimer's disease) as
pyranotacrines. These novel racemic Tacrine analogues are siginificantly less hepatotoxic than
Tacrine, retaining potent, and selective EeAChE inhibition with IC50 values in the M range,
with a remarkable antioxydant effect.
Yields are good in most cases. All prepared compounds were identified by the usual
spectroscopic methods (IR, 1H NMR and 13C NMR), and for some of them additional analyzes
were carried out (elemental analysis and / or X-ray diffraction).Diplôme : Doctorat En ligne : ../theses/chimie/BOU6833.pdf Format de la ressource électronique : Permalink : https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=10125 Synthèse, caractérisation et évaluation biologique de nouveaux dérivés poly-hétérocycliques à base d’imidazole [texte imprimé] / Houssem Boulebd, Auteur ; Ali Belfaitah, Directeur de thèse . - جامعة الإخوة منتوري قسنطينة, 2016 . - 257 f. ; 30 cm.
2 copies imprimes disponibles
Langues : Français (fre)
Catégories : Français - Anglais
ChimieTags : Chimie organique Imidazole halogénation poly-hétérocycles Maladie d’Alzheimer analogues de la
Tacrine hépatotoxicité ORAC activité biologique إيميدازول هلجنة متعدد الحلقات الغير متجانسة مرض الزهايمر نظائرالتاكرين سمية ORACفعالية بيولوجية
Imidazole halogenation poly-heterocyclic compounds Alzheimer's disease
tacrine analogues hepatotoxicity biological activityIndex. décimale : 540 Chimie et sciences connexes Résumé : Some 2-halo-(1-methyl-1H-imidazole) derivatives were prepared by selective halogenation
reaction (bromination, chlorination and iodination). The addition of -bromoacetophenone to
2-bromo(chloro)-1-methyl-1H-imidazole allowed us to access to corresponding imidazolium
salts in satisfactory yields (47-64%). The reactivity of 2-halogeno-N-phenyl-1-methyl-1Himidazolium bromide with activated methylene compounds of diverse structures has been
studied.
A series of original heterocyclic products composed of a core 1-methyl-1H-imidazole
associated at 2-position to highly functionalized heterocyclic compounds such as 4H-pyran,
chromene, benzo (pyrido) chromenes, 1,4-dihydropyridine, pyridine, quinazoline, pyrrolidines
and other pyrazolines have been prepared.
It will be noted that upon addition of methyl ketone derivatives, 1-methylimidazole-pyridine
hybrid compounds obtained are accompanied by the formation of corresponding 2,6-
dicyanoaniline derivatives in low yields. The adaptation of the operating conditions enabled us
to selectively direct the reaction towards the formation of new 2,6-dicyanoaniline derivatives
in good yields for aliphatic methyl ketone derivatives (62-70%), and in 45 % of yield for
acetophenone. These compounds are also fluorescent.
Some series of hybrid compounds such as (1-methyl-1H-imidazol-2-yl)-4H-pyran, -
pyridine, -1,4-dihydropyridine and -quinazoline have been subjected to an in vitro assessment
of their antimicrobial, and antioxydante (DPPH) activities, and also for their hepatotoxicity
towards liver cells HepG2 in a gradient concentration from 1M to 300M, and a structureactivity relationship (SAR) has been demonstrated.
A "valorization" of (1-methyl-1H-imidazol-2-yl)-4-pyran hybrid derivatives was undertaken
and resulted in the preparation of some original series of highly and diversely functionalized
Tacrine analogues (Tacrine is a drug used in the treatment of Alzheimer's disease) as
pyranotacrines. These novel racemic Tacrine analogues are siginificantly less hepatotoxic than
Tacrine, retaining potent, and selective EeAChE inhibition with IC50 values in the M range,
with a remarkable antioxydant effect.
Yields are good in most cases. All prepared compounds were identified by the usual
spectroscopic methods (IR, 1H NMR and 13C NMR), and for some of them additional analyzes
were carried out (elemental analysis and / or X-ray diffraction).Diplôme : Doctorat En ligne : ../theses/chimie/BOU6833.pdf Format de la ressource électronique : Permalink : https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=10125 Exemplaires (1)
Code-barres Cote Support Localisation Section Disponibilité BOU/6833 BOU/6833 Thèse Bibliothèque principale Thèses Disponible
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