| 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
Chimie
|
| Tags : |
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 : |
pdf |
| Permalink : |
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
Chimie
|
| Tags : |
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 : |
pdf |
| Permalink : |
index.php?lvl=notice_display&id=11058 |
|
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