The crude oil of Parthenocissus quinquefolia (L.) Planch seed was extracted by soxhlet method usi... more The crude oil of Parthenocissus quinquefolia (L.) Planch seed was extracted by soxhlet method using hexane. The physicochemical properties, fatty acid composition and DPPH radical-scavenging capacity of seed oil were evaluated. The fatty acids profile was obtained using gas chromatography and physicochemical properties were determined using standard methods. The fatty acid profile revealed twenty compounds with linoleic acid (48.23%), palmitic acid (20.61%) and oleic acid (21.96%) as predominant compounds. H and C NMR spectroscopy analysis of the oil were also carried out and they served to confirm the existence of fatty acid chains as glycerides. Physicochemical characteristics of the oil were determined as follows: moisture (1.37%), clour (dark yellowish green), specific extinction coefficient K232, K268 (0.51 and 1.08, respectively), iodine value (95.59 g I2/100g), peroxide value (5.13 mEq/Kg). These characteristics are very vital in considering the oil quality. Also, a saponific...
To explore a new set of anticancer agents, a novel series of pyrazolo[4,3-e]pyrido[1,2-a]pyrimidi... more To explore a new set of anticancer agents, a novel series of pyrazolo[4,3-e]pyrido[1,2-a]pyrimidine derivatives 7a-l have been designed and synthesized via cyclocondensation reactions of pyrazolo-enaminone 5 with a series of arylidene malononitriles; compound 5 was obtained from 5-amino-4-cyanopyrazole (3). The structures of the target compounds 7a-l were investigated by spectral techniques and elemental analysis (IR, UV-Vis, 1H NMR, 13C NMR and ESI-MS). All compounds were evaluated for their in vitro cytotoxicity employing a panel of different human tumor cell lines, A375, HT29, MCF7, A2780, FaDu as well as non-malignant NIH 3T3 and HEK293 cells. It has been found that the conjugate 7e was the most active towards many cell lines with EC50 values ranging between 9.1 and 13.5 µM, respectively. Moreover, in silico docking studies of 7e with six anticancer drug targets, i.e. DHFR, VEGFR2, HER-2/neu, hCA-IX, CDK6 and LOX also was performed, in order to gain some insights into their puta...
Abstract Carbohydrates are the main source of calories in most diets, and α-amylase is considered... more Abstract Carbohydrates are the main source of calories in most diets, and α-amylase is considered one of the main enzymes that initiate their digestion. The inhibition of α-amylase is therefore considered to be a therapeutic strategy for the treatment of disorders of glucose absorption, such as dental caries, periodontal disease, overweight, obesity and diabetes. On the other hand, flavonoids, isoxazoles and halogenated derivatives are of great interest in medicinal chemistry due to their considerable bioactivities. Therefore, this work describes the design, the synthesis and the α-amylase inhibitory potential of new halogenated flavonoid-based isoxazoles, and their biological properties. In fact, the condensation of a previously synthesized halogenated flavonol with different aryl nitrile oxides afford thirteen new hybrid cycloadducts (2a-m). Their structures were characterized by 1H NMR, 13C NMR and HRMS analysis. The physicochemical properties of these compounds (2a-m) were also evaluated. The newly synthesized cycloadducts were evaluated in vitro for their α-amylase inhibitory activity and excellent results were noted. The compound 2b (IC50 = 16.2 ± 0.3 µM) exhibited the highest anti-α-amylase activity comparable to that of the standard substance (Acarbose, IC50 = 15.7 ± 0.2 µM). The study of the Structure-Activity Relationship (SAR) was sufficiently discussed based on the Molecular Docking analysis and the Density Functional Theory (DFT) studies.
A series of N-tosyl α-amino acids 2a-e, prepared using a tosyl chloride protecting group, was con... more A series of N-tosyl α-amino acids 2a-e, prepared using a tosyl chloride protecting group, was condensed with (±)-vasicinone 1, isolated from the seeds of the plant Peganum harmala, to generate the corresponding esters 3a-e and 3b′-e′. (±)-Vasicinone 1 was also reacted with chloroacetic acid chloride to afford a new chlorinated ester 4 which was refluxed with trialkyl phosphites to give 2 new phosphonates 5a,b. All synthesized compounds were characterized with the help of spectroscopic means, including NMR (1H, 13C, and 31P) and ES-HRMS, and then screened for their in vitro anti-acetylcholinesterase (AChE), anti-5-lipoxygenase (5-LOX), and cytotoxic activities (MCF-7, OVCAR-3, and HCT-116 cell lines). Most synthesized derivatives exhibited a cytotoxic activity against 3 cell lines used. The phosphonate derivative 5b was found to be the most active one (IC50 = 63.7 ± 1.4 µM) against AChE enzyme. Only 2 diastereoisomers 3e and 3e′ exhibited activity against 5-LOX enzyme with IC50 value...
Interesting biological activities (anti-inflammatory, anticancer, antiviral, antioxidant, antidia... more Interesting biological activities (anti-inflammatory, anticancer, antiviral, antioxidant, antidiabetic…) have been reported for maslinic acid (MA) and MA-based compounds. In continuation of our previous work on MA, herbicide potential of Tunisian plant extracts and 1,4-triazolyl derivatives of MA, we now wish to report semisynthesis of new MA-based triazole hybrid compounds with herbicide potential. These compounds were synthesized through Cu-catalyzed azide-alkyne cycloaddition (CuAAC) under microwave irradiation conditions between propargylated MA and a series of phthalimide azides. Here, the first partner of CuAAC reaction (propargylated MA) resulted from propargylation of C-28 carboxylic acid group of isolated MA from the well-known Mediterranean plant Olea europaea L. (Oleaceae). So far, phthalimide azide derivatives were achieved by trapping of N-acyliminium ion, in-situ generated under catalytic condition of Bi(OTf), by aromatic nucleophiles. The cycloaddition reaction afford...
Journal of Enzyme Inhibition and Medicinal Chemistry, 2014
Abstract In our study, a series of new harmine derivatives has been prepared by cycloaddition rea... more Abstract In our study, a series of new harmine derivatives has been prepared by cycloaddition reaction using various arylnitrile oxides and evaluated in vitro against acetylcholinesterase and 5-lipoxygenase enzymes, MCF7 and HCT116 cancer cell lines. Some of these molecules have been shown to be potent inhibitors of acetylcholinesterase and MCF7 cell line. The greatest activity against acetylcholinesterase (IC50 = 10.4 µM) was obtained for harmine 1 and cytotoxic activities (IC50 = 0.2 µM) for compound 3a. Two derivatives 3e and 3f with the thiophene and furan systems, respectively, showed good activity against 5- lipoxygenase enzyme (IC50 = 29.2 and 55.5 µM, respectively).
The crude oil of Parthenocissus quinquefolia (L.) Planch seed was extracted by soxhlet method usi... more The crude oil of Parthenocissus quinquefolia (L.) Planch seed was extracted by soxhlet method using hexane. The physicochemical properties, fatty acid composition and DPPH radical-scavenging capacity of seed oil were evaluated. The fatty acids profile was obtained using gas chromatography and physicochemical properties were determined using standard methods. The fatty acid profile revealed twenty compounds with linoleic acid (48.23%), palmitic acid (20.61%) and oleic acid (21.96%) as predominant compounds. H and C NMR spectroscopy analysis of the oil were also carried out and they served to confirm the existence of fatty acid chains as glycerides. Physicochemical characteristics of the oil were determined as follows: moisture (1.37%), clour (dark yellowish green), specific extinction coefficient K232, K268 (0.51 and 1.08, respectively), iodine value (95.59 g I2/100g), peroxide value (5.13 mEq/Kg). These characteristics are very vital in considering the oil quality. Also, a saponific...
To explore a new set of anticancer agents, a novel series of pyrazolo[4,3-e]pyrido[1,2-a]pyrimidi... more To explore a new set of anticancer agents, a novel series of pyrazolo[4,3-e]pyrido[1,2-a]pyrimidine derivatives 7a-l have been designed and synthesized via cyclocondensation reactions of pyrazolo-enaminone 5 with a series of arylidene malononitriles; compound 5 was obtained from 5-amino-4-cyanopyrazole (3). The structures of the target compounds 7a-l were investigated by spectral techniques and elemental analysis (IR, UV-Vis, 1H NMR, 13C NMR and ESI-MS). All compounds were evaluated for their in vitro cytotoxicity employing a panel of different human tumor cell lines, A375, HT29, MCF7, A2780, FaDu as well as non-malignant NIH 3T3 and HEK293 cells. It has been found that the conjugate 7e was the most active towards many cell lines with EC50 values ranging between 9.1 and 13.5 µM, respectively. Moreover, in silico docking studies of 7e with six anticancer drug targets, i.e. DHFR, VEGFR2, HER-2/neu, hCA-IX, CDK6 and LOX also was performed, in order to gain some insights into their puta...
Abstract Carbohydrates are the main source of calories in most diets, and α-amylase is considered... more Abstract Carbohydrates are the main source of calories in most diets, and α-amylase is considered one of the main enzymes that initiate their digestion. The inhibition of α-amylase is therefore considered to be a therapeutic strategy for the treatment of disorders of glucose absorption, such as dental caries, periodontal disease, overweight, obesity and diabetes. On the other hand, flavonoids, isoxazoles and halogenated derivatives are of great interest in medicinal chemistry due to their considerable bioactivities. Therefore, this work describes the design, the synthesis and the α-amylase inhibitory potential of new halogenated flavonoid-based isoxazoles, and their biological properties. In fact, the condensation of a previously synthesized halogenated flavonol with different aryl nitrile oxides afford thirteen new hybrid cycloadducts (2a-m). Their structures were characterized by 1H NMR, 13C NMR and HRMS analysis. The physicochemical properties of these compounds (2a-m) were also evaluated. The newly synthesized cycloadducts were evaluated in vitro for their α-amylase inhibitory activity and excellent results were noted. The compound 2b (IC50 = 16.2 ± 0.3 µM) exhibited the highest anti-α-amylase activity comparable to that of the standard substance (Acarbose, IC50 = 15.7 ± 0.2 µM). The study of the Structure-Activity Relationship (SAR) was sufficiently discussed based on the Molecular Docking analysis and the Density Functional Theory (DFT) studies.
A series of N-tosyl α-amino acids 2a-e, prepared using a tosyl chloride protecting group, was con... more A series of N-tosyl α-amino acids 2a-e, prepared using a tosyl chloride protecting group, was condensed with (±)-vasicinone 1, isolated from the seeds of the plant Peganum harmala, to generate the corresponding esters 3a-e and 3b′-e′. (±)-Vasicinone 1 was also reacted with chloroacetic acid chloride to afford a new chlorinated ester 4 which was refluxed with trialkyl phosphites to give 2 new phosphonates 5a,b. All synthesized compounds were characterized with the help of spectroscopic means, including NMR (1H, 13C, and 31P) and ES-HRMS, and then screened for their in vitro anti-acetylcholinesterase (AChE), anti-5-lipoxygenase (5-LOX), and cytotoxic activities (MCF-7, OVCAR-3, and HCT-116 cell lines). Most synthesized derivatives exhibited a cytotoxic activity against 3 cell lines used. The phosphonate derivative 5b was found to be the most active one (IC50 = 63.7 ± 1.4 µM) against AChE enzyme. Only 2 diastereoisomers 3e and 3e′ exhibited activity against 5-LOX enzyme with IC50 value...
Interesting biological activities (anti-inflammatory, anticancer, antiviral, antioxidant, antidia... more Interesting biological activities (anti-inflammatory, anticancer, antiviral, antioxidant, antidiabetic…) have been reported for maslinic acid (MA) and MA-based compounds. In continuation of our previous work on MA, herbicide potential of Tunisian plant extracts and 1,4-triazolyl derivatives of MA, we now wish to report semisynthesis of new MA-based triazole hybrid compounds with herbicide potential. These compounds were synthesized through Cu-catalyzed azide-alkyne cycloaddition (CuAAC) under microwave irradiation conditions between propargylated MA and a series of phthalimide azides. Here, the first partner of CuAAC reaction (propargylated MA) resulted from propargylation of C-28 carboxylic acid group of isolated MA from the well-known Mediterranean plant Olea europaea L. (Oleaceae). So far, phthalimide azide derivatives were achieved by trapping of N-acyliminium ion, in-situ generated under catalytic condition of Bi(OTf), by aromatic nucleophiles. The cycloaddition reaction afford...
Journal of Enzyme Inhibition and Medicinal Chemistry, 2014
Abstract In our study, a series of new harmine derivatives has been prepared by cycloaddition rea... more Abstract In our study, a series of new harmine derivatives has been prepared by cycloaddition reaction using various arylnitrile oxides and evaluated in vitro against acetylcholinesterase and 5-lipoxygenase enzymes, MCF7 and HCT116 cancer cell lines. Some of these molecules have been shown to be potent inhibitors of acetylcholinesterase and MCF7 cell line. The greatest activity against acetylcholinesterase (IC50 = 10.4 µM) was obtained for harmine 1 and cytotoxic activities (IC50 = 0.2 µM) for compound 3a. Two derivatives 3e and 3f with the thiophene and furan systems, respectively, showed good activity against 5- lipoxygenase enzyme (IC50 = 29.2 and 55.5 µM, respectively).
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Papers by Hichem Jannet