Anis Romdhane
University of Monastir
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Featured researches published by Anis Romdhane.
Tetrahedron Letters | 2000
Abdallah Harizi; Anis Romdhane; Zine Mighri
Abstract The reaction of aromatic primary amines 1 with carbon disulfide in the presence of a catalytic amount of triethylamine followed by treatment with aqueous hydrogen peroxide leads to the corresponding benzoxa(thia)zol-2-thiones 3a – c which can be transformed with iminoethers into 2-alkylthiobenzoxa(thia)zoles 5a – h in good yields (64–85%).
Bioorganic Chemistry | 2016
Ameur Rahmouni; Sawssen Souiei; Mohamed Amine Belkacem; Anis Romdhane; Jalloul Bouajila; Hichem Ben Jannet
A novel series of 6-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-ones 3a-h were synthesized in a single step via condensation of carboxamide 2 with some aromatic aldehydes (presence of iodine). Treatment of aminopyrazole 1a with acetic anhydride afforded pyrazolopyrimidines 4 which on treatment with ethyl chloroacetate in refluxing dry DMF furnished a single product identified as ethyl 2-(3,6-dimethyl-4-oxo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-5(4H)-yl) acetate 5. On the other hand, esterification of compound 6 with different alcohol, led to the formation of new esters linked pyrazolo[3,4-d]pyrimidinones hybrids 7a-f. The reaction of compound 2 with 3-propargyl bromide gave the compound 8 used as a dipolarophile to access to triazoles (4- and 5-regioisomers (9a-e) and (10a-e), respectively) via the 1,3-dipoar cycloaddition reaction. Finally, condensation reaction of aminopyrazole 1b with α-cyanocinnamonitiles gave the new pyrazolo[1,5-a]pyrimidine-3,6-dicarbonitriles 11a-e. Structures of compounds were established on the basis of (1)H/(13)C NMR and ESI-HRMS. Compounds were screened for their cytotoxic (HCT-116 and MCF-7) and 5-lipoxygenase inhibition activities. The structure-activity relationship (SAR) was discussed.
Medicinal Chemistry | 2016
Insaf Filali; Anis Romdhane; Mansour Znati; Hichem Ben Jannet; Jalloul Bouajila
Harmine 1 was extracted from the seeds of Peganum harmala. From this natural molecule, a new series of isoxazole derivatives with complete regiospecificity were prepared using 1,3-dipolar cycloaddition reactions with various arylnitrile oxides. Harmine and its derivatives were characterized by (1)H NMR, (13)C NMR and HRMS. The evaluation of their anti-acetylcholinesterase (AChE), anti-5-lipoxygenase (5-LOX), anti-xanthine oxidase (XOD) and anticancer activities were studied in vitro against AChE, 5-LOX and XOD enzymes, respectively, and in HTC-116, MCF7 and OVCAR-3 cancer cell lines. The prepared derivatives were shown to be inactive against the XOD enzyme (0-38.3 ± 1.9% at 100 µM). Compound 2 exhibited the best anti-AChE activity (IC50=1.9 ± 1.5 µM). Derivatives 3a, 3b and 3d had moderate cytotoxic activities (IC50=5.0 ± 0.3 µM (3a) and IC50=6.3 ± 0.4 µM (3b) against HCT 116 cells, IC50=5.0 ± 1.0 µM (3d) against MCF7 cells).
Medicinal Chemistry Research | 2015
Sined Medimagh-Saidana; Anis Romdhane; Mejda Daami-Remadi; Haifa Jabnoun-Khiareddine; David Touboul; Hichem Ben Jannet; M’hamed Ali Hamza
AbstractConsidering the potential interest of heterocyclic compounds, the aim of the present study is to synthesize new coumarin derivatives, to provide their full chemical characterization and to evaluate their antimicrobial activities. The reaction of ethyl 2-(4-methyl-2-oxo-2H-chromen-7-yloxy) acetate 2 with sodium hydroxide afforded the corresponding 2-(2-oxo-4-methyl-2H-chromen-7-yloxy) acetic acid 3 which was esterified using a series of alcohols in the presence of iodine to yield a new series of coumarin esters 4a–j. On the other hand, treatment of the key intermediate 2 with an aqueous solution of hydrazine in ethanol at reflux gave the corresponding hydrazide 5 which further converted into coumarin derivatives 6a–f and 7a–c by condensation with a series of aromatic aldehydes and cyclic anhydrides, respectively. The synthesized compounds were completely characterized by 1H NMR, 13C NMR, IR and HRMS. The antibacterial and antifungal activities of the new synthesized compounds were evaluated using the disc diffusion method and seemed to be significant.
Phosphorus Sulfur and Silicon and The Related Elements | 2012
Anis Romdhane; Jean-François Gallard; M’hamed Ali Hamza; Hichem Ben Jannet
Abstract The synthesis of new naphthopyranotriazolopyrimidines phosphonates 4a–i in good yields (74%–93%) has been accomplished via Michaelis–Arbusov rearrangement by the reaction of trialkyl phosphite with naphthopyranotriazolopyrimidines chloride 3a–e, which were obtained from α-functionalized iminoethers 1 in two steps. The synthesized compounds 4a–i were completely characterized by IR, 1H, 13C, and 31P NMR and HRMS. Supplemental materials are available for this article. Go to the publishers online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT
Journal of Enzyme Inhibition and Medicinal Chemistry | 2016
Marwa Zayane; Ameur Rahmouni; Mejda Daami-Remadi; Mohamed Ben Mansour; Anis Romdhane; Hichem Ben Jannet
Abstract We designed and synthesized new series of diverse triazoles, isoxazoles, isoxazolines, and aziridines linked 4-methylumbelliferone 1 using intermolecular 1,3-dipolar cycloaddition reactions. Structures of these compounds were established on the basis of 1H NMR, 13C NMR, and ESI-HRMS. All prepared compounds were evaluated for their antimicrobial, anticoagulant, and anticholinesterase activities. Interestingly, among the tested molecules, some of the analogs displayed better activities than the parent 4-methylumbelliferone 1 such as 6a and 6d for their antifungal properties. Moreover, compounds 4, 5, 6, and 7 showed the importance of the added fragments to 4-methylumbelliferone 1 via the linker methylene to have good activity.
Journal of Chemical Sciences | 2015
Marwa Zayane; Anis Romdhane; Mejda Daami-Remadi; Hichem Ben Jannet
AbstractSynthesis of some novel coumarin esters has been accomplished through iodine-catalyzed method using 4-methylumbelliferone as the starting material. Condensation of hydrazide, which was obtained in two steps from 4-methylumbelliferone, with some arylaldhydes provided hydrazone derivatives, while the reaction with phenylthioisocyanate leads to the thiosemicarbazide that evolved into two new compounds. Finally, condensation reaction of hydrazide with three diketones afforded new pyrrole and pyrazole derivatives. Structures of all synthesized compounds were established on the basis of spectroscopic methods including 1H NMR, 13C NMR and ES-HRMS. They were finally tested for their antimicrobial activity and the structure-activity relationship was discussed. Graphical AbstractA new series of compounds were synthesized from 4-methylumbelliferone. All the new compounds were characterized by spectral data and subsequently evaluated for their antimicrobial activity.
Bioorganic Chemistry | 2019
Meriem Debbabi; Vijaykumar D. Nimbarte; Samia Chekir; Sarra Chortani; Anis Romdhane; Hichem Ben Jannet
Pyrimidine-fused compounds are of great interest for the discovery of potent bioactive agents. This study describes the synthesis of novel pyranopyrimidines 3a-f and pyranotriazolopyrimidines 4a-d derivatives via the cyclocondensation reaction of α-functionalized iminoether 2, which was obtained from 2-amino-3-cyanopyrane 1, with a series of primary aromatic amines and hydrazides, respectively. Structures of all synthesized compounds were established on the basis of spectroscopic methods including 1H NMR, 13C NMR and ES-HRMS. They were finally tested for their anticoagulant and anti-tyrosinase activities. Significant results have been obtained and the structure-activity relationship (SAR) was discussed with the help of molecular docking analysis.
Journal of Pharmacy and Pharmacology | 2018
Mansour Znati; Meriem Debbabi; Anis Romdhane; Hichem Ben Jannet; Jalloul Bouajila
This work describes the synthesis, the bioactivity and the structure–activity relationship of new derivatives from a natural coumarin.
Journal of Enzyme Inhibition and Medicinal Chemistry | 2016
Abderrahim Ben Said; Anis Romdhane; Nicolas Elie; David Touboul; Hichem Ben Jannet; Jalloul Bouajila
Abstract The synthesis of 14-(aryl)-14H-naphto[2,1-b]pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-yl) acetamidoximes 2a–e has been accomplished by reaction of 2-acetonitrile derivatives 1a–e with hydroxylamine. Cyclocondensation reaction of precursors 2a–e with some elctrophilic species such as ethylorthoformate, acetic anhydride, and methyl-acetoacetate provided the new oxadiazole derivatives 3a–e, 4a–e, and 5a–e, respectively. On the other hand, the reaction of precursors 2a–e with 2-chloropropanoyl chloride afforded the new acetimidamides 6a–e which evolve under reflux of toluene to the new oxadiazoles 7a–e. The synthetic compounds were screened for their anti-xanthine oxidase, anti-soybean lipoxygenase, and cytotoxic activities. Moderate to weak xanthine oxidase and soybean lipoxygenase inhibitions were obtained but significant cytotoxic activities were noted. The most cytotoxic activities were recorded mainly (i) 5a was the most active (IC50 = 4.0 μM) and selective against MCF-7 and (ii) 2a was cytotoxic against the four cell lines with selectivity for MCF-7 and OVCAR-3 (IC50 = 17 and 12 μM, respectively) while 2e is highly selective against OVCAR-3 (IC50 = 10 μM).