Obesity is a serious health problem that increases the risk of many complications, including diab... more Obesity is a serious health problem that increases the risk of many complications, including diabetes and cardiovascular disease. This study aims to evaluate, for the first time, the effects of oxaziridine 3 on lipoprotein lipase activity in the serum of rats fed with a high-fat diet (HFD) on body weight, lipid profile and liver-kidney functions. The administration of oxaziridine 3 to HFD-rats lowered body weight and inhibited the lipase activity of obese rats leading to notable decrease of T-Ch, TGs and LDL-Ch levels accompanied with an increase in HDL-Ch concentration in serum. Moreover, the findings of this study revealed that oxaziridine 3 helped to protect liver tissue from the appearance of fatty cysts. Additionally, oxaziridine 3 administration to HFD-rats induces antioxidant activity proven by the increase of superoxide dismutase (SOD) and catalase (CAT) activities and the decrease in Thiobarbituric acid reactive substances (TBARS) levels. It also induces the protection of liver-kidney functions confirmed by a decrease in the levels of toxicity parameters in blood. 2016 Elsevier Masson SAS. All rights reserved.
This is a corrigendum to the article 'Inhibition of Key Digestive Enzymes Related to Diabetes and... more This is a corrigendum to the article 'Inhibition of Key Digestive Enzymes Related to Diabetes and Hyperlipidemia and Protection of Liver-Kidney Functions by Trigonelline in Diabetic Rats' [Sci Pharm. 2013; 81: 233-246]. Figure 6 is replaced.
Naturally occurring hydroxamic acid derivatives are biosynthesized by microorganisms (siderophore... more Naturally occurring hydroxamic acid derivatives are biosynthesized by microorganisms (siderophores) and plants (benzoxazinoids). Recent developments in drug related research have highlighted the promising biological and pharmacological properties that the hydroxamic acid function may offer for the enhancement of therapeutic applications. This study reports on the full synthesis of a new dihydroisoquinoline hydroxamic acid (2-Hydroxy-3,3-dimethyl-7-nitro-3,4dihydroisoquinolin-1(2H)-one). It also describes its cytotoxicity with regard to the human hepatocarcinoma cell line Hep3B.
Deux nouveaux sels d'oxaziridinium isoquinoleiques diversement substitues ont ete prepares da... more Deux nouveaux sels d'oxaziridinium isoquinoleiques diversement substitues ont ete prepares dans un premier temps et leurs reactivites ont ete comparees a celle de l'analogue non substitue. Ce dernier a une reactivite principalement electrophile mais aussi acide (en de l'azote) qui se manifeste vis-a-vis des nucleophiles basiques ou dans des milieux basiques. Ces deux nouveaux oxaziridiniums resultent de deux approches mis en uvre pour maitriser la double reactivite et atteindre un maximum de reactivite electrophile (transfert d'oxygene). Les deux nouveaux modeles sont des agents de transfert d'oxygene largement plus efficaces que le modele de reference non substitue et notamment en tant qu'agents d'epoxydation aussi bien dans des reactions stoechiometriques que catalytiques. Un troisieme sel d'oxaziridinium comportant les caracteristiques structurales et cumulant les avantages inherents a chacun des deux precedents a ensuite ete synthetise. C'est ...
Abstract Models of dihydroisoquinoline oxaziridines substituted in position 1 were synthesized fr... more Abstract Models of dihydroisoquinoline oxaziridines substituted in position 1 were synthesized from the peracidic oxidation of imines and characterized through the IR, elemental analysis and NMR spectral studies; the crystal structure of 3d was determined from single crystal X-ray diffraction data. All these compounds were evaluated for their antimicrobial activity.
Palladium-catalyzed oxidative C−H halogenation and acetoxylation reactions of S-unprotected sulfi... more Palladium-catalyzed oxidative C−H halogenation and acetoxylation reactions of S-unprotected sulfides, selectively directed by pyridinyl groups, allows the formation of C−X bonds (X = I, Br, Cl, OAc) by using simple halosuccinimide or phenyliodine diacetate (PIDA) oxidants. The undesired formation of sulfoxides and/or sulfones, which are usually observed under oxidative conditions, is fully obviated. Under the solvent-dependent conditions that we proposed, sulfide C−H functionalization is achieved in less than 1 h without any direct electrophilic halogenation at the pyridine moiety. N-Directed ortho-C−H activation of aryl also facilitates dibromination reactions which are hardly accessible with sulfone and sulfoxide counterparts because of their higher structural rigidity. This general method gives a straightforward access to polyhalide sulfides, without an organosulfur reduction step or protection−deprotection sequence. Polyhalide sulfides are valuable synthons that give a practical entry to new constrained polyaromatic and biphenyl sulfides, including synthetically challenging unsymmetrical examples.
Oleuropein is the major phenolic compound extracted from olive leaves and it is also present in o... more Oleuropein is the major phenolic compound extracted from olive leaves and it is also present in olive fruits and virgin olive oil. It has already demonstrated a wide range of pharmacological activities, but new derivatives have to be designed in order to obtain useful Structure-Activity Relationships for this family of products, as well as new analogs with improved and/or different biological properties. However, taking into account the multiple OH groups (catechol and sugar) present in oleuropein, the selective modification of this natural product is a challenging problem. In this paper, we present an efficient strategy allowing the selective modification at the primary alcohol position of this natural product. Using appropriate protection/deprotection sequences, we prepared by hemisynthesis several triazoles linked to the oleuropein core, as representative examples for the development of such an approach.
Gaillonia eriantha is a member of family Paederieae (Rubiaceae). The essential oil of G. eriantha... more Gaillonia eriantha is a member of family Paederieae (Rubiaceae). The essential oil of G. eriantha growing wild in south of Iran was obtained by hydrodistillation and analysed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). Antioxidante activity and polyphenolic content were identified by DPPH microplate method and HPLC-DAD, respectively. Twenty-two compounds were identified in the oil. The major volatile compounds were camphor (14.8%), octyl formate (14.7%), 1,8-cineole (10.9%), n-decane (8.1%), n-undecane (6.8%), n-dodecane (6.1%), n-nonane(5.4%) and α-agarofuran (5.2%). The antioxidant activity of the extract of G. eriantha was found to be 786.57 μg/mL. It was found that the predominant phenolic constituents were chlorogenic acid (2.23 mg/g), catechin (0.37 mg/g), hesperidin (0.13 mg/g), trans-ferulic acid (0.12 mg/g), caffeic acid (0.051 mg/g), carvacrol (0.028 mg/g) and vanillin (0.021 mg/g), respectively.
The title salt, C13H17N2O2+·BF4−, was prepared by the methylation of the imine with Meerwein salt... more The title salt, C13H17N2O2+·BF4−, was prepared by the methylation of the imine with Meerwein salt in dichloromethane. The asymmetric unit comprises a 1,3,3-trimethyl-7-nitro-3,4-dihydroisoquinolinium cation and a tetrafluoroborate anion. The coordination around the boron atom in the tetrafluoroborate anion is tetrahedral. The heterocyclic ring adopts a half-chair conformation. The crystal packing is governed by means of C—H...F contacts, which lead to the formation of a three-dimensional network.
The heck reaction of aryl bromide with styrene in N,N-dimethyl formamide/water as solvent has bee... more The heck reaction of aryl bromide with styrene in N,N-dimethyl formamide/water as solvent has been studied using different catalysts under ultrasonic irradiation at room temperature. The effect of the solvent, the base, and the catalyst of the transfer phase were studied. The results show that ultrasonic irradiation increases the heck reaction yield and becomes faster with the amount of aliquat-336.
Without phosphine and base, palladium catalysts such as PdCl 2 , Pd(OAc) 2 and PdCl 2 (PhCN) 2 in... more Without phosphine and base, palladium catalysts such as PdCl 2 , Pd(OAc) 2 and PdCl 2 (PhCN) 2 in water/ DMF mixtures with Aliquat-336 proved to be excellent catalytic systems for Heck reactions involving several aryl bromides with styrene and acrylic compounds. Yields are remarkably improved under ultrasonic irradiation and the products show a high purity.
ABSTRACT N-Alkyl-oxaziridines react in the presence of a nucleophile as an oxygenating agent; in ... more ABSTRACT N-Alkyl-oxaziridines react in the presence of a nucleophile as an oxygenating agent; in the absence of a nucleophile, an isomerization reaction is observed. This study describes the synthesis of two new dihydroisoquinoline oxaziridines and their reactivity in an acid-promoted reaction in the presence and absence of sulfides.
N-Alkyl oxaziridines react as oxygenating reagents in the presence of a nucleophile. In this work... more N-Alkyl oxaziridines react as oxygenating reagents in the presence of a nucleophile. In this work, we describe the synthesis of new dihydroisoquinoline oxaziridines, and their reactivity in an acid-promoted reaction both in presence and in absence of sulfides. In the absence of sulfides, a new nitrone is produced.
This paper describes the synthesis of a series of dihydroisoquinoline nitrones by isomerization o... more This paper describes the synthesis of a series of dihydroisoquinoline nitrones by isomerization of the corresponding oxaziridines. Nitrones4a–cwere obtained in excellent yields and high purity by a simple and effective method from the isomerization of oxaziridines. The synthesized compounds were also evaluated for their antibacterial activity against Gram-positive and Gram-negative bacteria and fungus.
The nicely crystalline, easily prepared and handled, 3,3-dimethyl-3,4-dihydroisoquinolinium salt ... more The nicely crystalline, easily prepared and handled, 3,3-dimethyl-3,4-dihydroisoquinolinium salt 6, is a convenient catalyst for the oxaziridinium-mediated epoxidation of alkenes by Oxone ® .
Obesity is a serious health problem that increases the risk of many complications, including diab... more Obesity is a serious health problem that increases the risk of many complications, including diabetes and cardiovascular disease. This study aims to evaluate, for the first time, the effects of oxaziridine 3 on lipoprotein lipase activity in the serum of rats fed with a high-fat diet (HFD) on body weight, lipid profile and liver-kidney functions. The administration of oxaziridine 3 to HFD-rats lowered body weight and inhibited the lipase activity of obese rats leading to notable decrease of T-Ch, TGs and LDL-Ch levels accompanied with an increase in HDL-Ch concentration in serum. Moreover, the findings of this study revealed that oxaziridine 3 helped to protect liver tissue from the appearance of fatty cysts. Additionally, oxaziridine 3 administration to HFD-rats induces antioxidant activity proven by the increase of superoxide dismutase (SOD) and catalase (CAT) activities and the decrease in Thiobarbituric acid reactive substances (TBARS) levels. It also induces the protection of liver-kidney functions confirmed by a decrease in the levels of toxicity parameters in blood. 2016 Elsevier Masson SAS. All rights reserved.
This is a corrigendum to the article 'Inhibition of Key Digestive Enzymes Related to Diabetes and... more This is a corrigendum to the article 'Inhibition of Key Digestive Enzymes Related to Diabetes and Hyperlipidemia and Protection of Liver-Kidney Functions by Trigonelline in Diabetic Rats' [Sci Pharm. 2013; 81: 233-246]. Figure 6 is replaced.
Naturally occurring hydroxamic acid derivatives are biosynthesized by microorganisms (siderophore... more Naturally occurring hydroxamic acid derivatives are biosynthesized by microorganisms (siderophores) and plants (benzoxazinoids). Recent developments in drug related research have highlighted the promising biological and pharmacological properties that the hydroxamic acid function may offer for the enhancement of therapeutic applications. This study reports on the full synthesis of a new dihydroisoquinoline hydroxamic acid (2-Hydroxy-3,3-dimethyl-7-nitro-3,4dihydroisoquinolin-1(2H)-one). It also describes its cytotoxicity with regard to the human hepatocarcinoma cell line Hep3B.
Deux nouveaux sels d'oxaziridinium isoquinoleiques diversement substitues ont ete prepares da... more Deux nouveaux sels d'oxaziridinium isoquinoleiques diversement substitues ont ete prepares dans un premier temps et leurs reactivites ont ete comparees a celle de l'analogue non substitue. Ce dernier a une reactivite principalement electrophile mais aussi acide (en de l'azote) qui se manifeste vis-a-vis des nucleophiles basiques ou dans des milieux basiques. Ces deux nouveaux oxaziridiniums resultent de deux approches mis en uvre pour maitriser la double reactivite et atteindre un maximum de reactivite electrophile (transfert d'oxygene). Les deux nouveaux modeles sont des agents de transfert d'oxygene largement plus efficaces que le modele de reference non substitue et notamment en tant qu'agents d'epoxydation aussi bien dans des reactions stoechiometriques que catalytiques. Un troisieme sel d'oxaziridinium comportant les caracteristiques structurales et cumulant les avantages inherents a chacun des deux precedents a ensuite ete synthetise. C'est ...
Abstract Models of dihydroisoquinoline oxaziridines substituted in position 1 were synthesized fr... more Abstract Models of dihydroisoquinoline oxaziridines substituted in position 1 were synthesized from the peracidic oxidation of imines and characterized through the IR, elemental analysis and NMR spectral studies; the crystal structure of 3d was determined from single crystal X-ray diffraction data. All these compounds were evaluated for their antimicrobial activity.
Palladium-catalyzed oxidative C−H halogenation and acetoxylation reactions of S-unprotected sulfi... more Palladium-catalyzed oxidative C−H halogenation and acetoxylation reactions of S-unprotected sulfides, selectively directed by pyridinyl groups, allows the formation of C−X bonds (X = I, Br, Cl, OAc) by using simple halosuccinimide or phenyliodine diacetate (PIDA) oxidants. The undesired formation of sulfoxides and/or sulfones, which are usually observed under oxidative conditions, is fully obviated. Under the solvent-dependent conditions that we proposed, sulfide C−H functionalization is achieved in less than 1 h without any direct electrophilic halogenation at the pyridine moiety. N-Directed ortho-C−H activation of aryl also facilitates dibromination reactions which are hardly accessible with sulfone and sulfoxide counterparts because of their higher structural rigidity. This general method gives a straightforward access to polyhalide sulfides, without an organosulfur reduction step or protection−deprotection sequence. Polyhalide sulfides are valuable synthons that give a practical entry to new constrained polyaromatic and biphenyl sulfides, including synthetically challenging unsymmetrical examples.
Oleuropein is the major phenolic compound extracted from olive leaves and it is also present in o... more Oleuropein is the major phenolic compound extracted from olive leaves and it is also present in olive fruits and virgin olive oil. It has already demonstrated a wide range of pharmacological activities, but new derivatives have to be designed in order to obtain useful Structure-Activity Relationships for this family of products, as well as new analogs with improved and/or different biological properties. However, taking into account the multiple OH groups (catechol and sugar) present in oleuropein, the selective modification of this natural product is a challenging problem. In this paper, we present an efficient strategy allowing the selective modification at the primary alcohol position of this natural product. Using appropriate protection/deprotection sequences, we prepared by hemisynthesis several triazoles linked to the oleuropein core, as representative examples for the development of such an approach.
Gaillonia eriantha is a member of family Paederieae (Rubiaceae). The essential oil of G. eriantha... more Gaillonia eriantha is a member of family Paederieae (Rubiaceae). The essential oil of G. eriantha growing wild in south of Iran was obtained by hydrodistillation and analysed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). Antioxidante activity and polyphenolic content were identified by DPPH microplate method and HPLC-DAD, respectively. Twenty-two compounds were identified in the oil. The major volatile compounds were camphor (14.8%), octyl formate (14.7%), 1,8-cineole (10.9%), n-decane (8.1%), n-undecane (6.8%), n-dodecane (6.1%), n-nonane(5.4%) and α-agarofuran (5.2%). The antioxidant activity of the extract of G. eriantha was found to be 786.57 μg/mL. It was found that the predominant phenolic constituents were chlorogenic acid (2.23 mg/g), catechin (0.37 mg/g), hesperidin (0.13 mg/g), trans-ferulic acid (0.12 mg/g), caffeic acid (0.051 mg/g), carvacrol (0.028 mg/g) and vanillin (0.021 mg/g), respectively.
The title salt, C13H17N2O2+·BF4−, was prepared by the methylation of the imine with Meerwein salt... more The title salt, C13H17N2O2+·BF4−, was prepared by the methylation of the imine with Meerwein salt in dichloromethane. The asymmetric unit comprises a 1,3,3-trimethyl-7-nitro-3,4-dihydroisoquinolinium cation and a tetrafluoroborate anion. The coordination around the boron atom in the tetrafluoroborate anion is tetrahedral. The heterocyclic ring adopts a half-chair conformation. The crystal packing is governed by means of C—H...F contacts, which lead to the formation of a three-dimensional network.
The heck reaction of aryl bromide with styrene in N,N-dimethyl formamide/water as solvent has bee... more The heck reaction of aryl bromide with styrene in N,N-dimethyl formamide/water as solvent has been studied using different catalysts under ultrasonic irradiation at room temperature. The effect of the solvent, the base, and the catalyst of the transfer phase were studied. The results show that ultrasonic irradiation increases the heck reaction yield and becomes faster with the amount of aliquat-336.
Without phosphine and base, palladium catalysts such as PdCl 2 , Pd(OAc) 2 and PdCl 2 (PhCN) 2 in... more Without phosphine and base, palladium catalysts such as PdCl 2 , Pd(OAc) 2 and PdCl 2 (PhCN) 2 in water/ DMF mixtures with Aliquat-336 proved to be excellent catalytic systems for Heck reactions involving several aryl bromides with styrene and acrylic compounds. Yields are remarkably improved under ultrasonic irradiation and the products show a high purity.
ABSTRACT N-Alkyl-oxaziridines react in the presence of a nucleophile as an oxygenating agent; in ... more ABSTRACT N-Alkyl-oxaziridines react in the presence of a nucleophile as an oxygenating agent; in the absence of a nucleophile, an isomerization reaction is observed. This study describes the synthesis of two new dihydroisoquinoline oxaziridines and their reactivity in an acid-promoted reaction in the presence and absence of sulfides.
N-Alkyl oxaziridines react as oxygenating reagents in the presence of a nucleophile. In this work... more N-Alkyl oxaziridines react as oxygenating reagents in the presence of a nucleophile. In this work, we describe the synthesis of new dihydroisoquinoline oxaziridines, and their reactivity in an acid-promoted reaction both in presence and in absence of sulfides. In the absence of sulfides, a new nitrone is produced.
This paper describes the synthesis of a series of dihydroisoquinoline nitrones by isomerization o... more This paper describes the synthesis of a series of dihydroisoquinoline nitrones by isomerization of the corresponding oxaziridines. Nitrones4a–cwere obtained in excellent yields and high purity by a simple and effective method from the isomerization of oxaziridines. The synthesized compounds were also evaluated for their antibacterial activity against Gram-positive and Gram-negative bacteria and fungus.
The nicely crystalline, easily prepared and handled, 3,3-dimethyl-3,4-dihydroisoquinolinium salt ... more The nicely crystalline, easily prepared and handled, 3,3-dimethyl-3,4-dihydroisoquinolinium salt 6, is a convenient catalyst for the oxaziridinium-mediated epoxidation of alkenes by Oxone ® .
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