| 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
Chimie
|
| Tags : |
Chimie organique Imidazole halogénation poly-hétérocycles Maladie d’Alzheimer analogues de la
Tacrine hépatotoxicité ORAC activité biologique ????????? ????? ????? ??????? ????? ??????? ??? ???????? ????????????? ???? ORAC?????? ????????
Imidazole halogenation poly-heterocyclic compounds Alzheimer's disease
tacrine analogues hepatotoxicity biological activity |
| Index. 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 : |
pdf |
| 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 . - [S.l.] : جامعة الإخوة منتوري قسنطينة, 2016 . - 257 f. ; 30 cm. 2 copies imprimes disponibles Langues : Français ( fre)
| Catégories : |
Français - Anglais
Chimie
|
| Tags : |
Chimie organique Imidazole halogénation poly-hétérocycles Maladie d’Alzheimer analogues de la
Tacrine hépatotoxicité ORAC activité biologique ????????? ????? ????? ??????? ????? ??????? ??? ???????? ????????????? ???? ORAC?????? ????????
Imidazole halogenation poly-heterocyclic compounds Alzheimer's disease
tacrine analogues hepatotoxicity biological activity |
| Index. 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 : |
pdf |
| Permalink : |
https://bu.umc.edu.dz/md/index.php?lvl=notice_display&id=10125 |
|
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