One-pot three-component Biginelli-type reaction to synthesize 3,4-dihydropyrimidine-2-(1H)-ones catalyzed by Co phthalocyanines: Synthesis, characterization, aggregation behavior and antibacterial activity.
The synthesis of a novel phthalonitrile derivative with pyridine-2-thiol and 2,4,6-trimethylphenylamine substituents functionalized groups and its peripherally tetrasubstituted cobalt phthalocyanine and cationic phthalocyanines complexes were reported. The aggregation investigations carried out in different concentrations indicate that Co Phthalocyanines compounds 3,4 do not have any aggregation behavior for the concentration range of 6×10(-4)-14×10(-6)M in DMSO. The ion binding properties of Co Phthalocyanines compounds 3,4 show the formation of stable complex with Co(2+). In addition 3,4-Dihydropyrimidin-2(1H)-one derivatives were synthesized by modified Biginelli cyclocondensation reaction catalyzed by MPc as Lewis base. The structures of the synthesized compounds have been successfully characterized by the spectroscopic methods (IR, (1)H NMR, (13C)NMR, UV-Vis, mass spectrometry, elemental analysis and NMR 2D). The influence of substrate/catalyst ratio, solvent was also investigated to find optimal reaction on this synthesis for getting the highest conversion. Different parameters were examined for finding optimal conditions of catalysis. In addition; the compounds 3-11 were investigated for antimicrobial activity. Most of them exhibited important antimicrobial activity.
Heterocyclic and Organometallic Chemistry Laboratory, Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif, 2050, Tunisia.
Rawdha
R
Medyouni
Heterocyclic and Organometallic Chemistry Laboratory, Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif, 2050, Tunisia.
Wissal
W
Elgabsi
Laboratory of Applied Chemistry and Natural Substances Resources and Environment, Faculty of Sciences, University of Carthage, Zarzouna-Bizerta, 7021, Tunisia.
Olfa
O
Naouali
Área de Química Inorgánica, Universidad d'Almeria 04120, Almería, Spain.
Antonio
A
Romerosa
Chemistry Department, College of Science and Arts, Qassim University, Al-Rass, Kingdom of Saudi Arabia.
Abdullah
A
Sulaiman Al-Ayed
Chemistry Department, College of Science and Arts, Qassim University, Al-Rass, Kingdom of Saudi Arabia; Laboratory of Applied Chemistry and Natural Substances Resources and Environment, Faculty of Sciences, University of Carthage, Zarzouna-Bizerta, 7021, Tunisia.
Lasaad
L
Baklouti
Heterocyclic and Organometallic Chemistry Laboratory, Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif, 2050, Tunisia; Chemistry Department, College of Science and Arts, Qassim University, Al-Rass, Kingdom of Saudi Arabia. Electronic address: naceur.hamdi@isste.rnu.tn.
Naceur
N
Hamdi
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D001424:Bacterial Infections / Q000188:drug therapy; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011744:Pyrimidinones / Q000737:chemistry / Q000494:pharmacology*; D013056:Spectrophotometry, Ultraviolet; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D007211:Indoles; D009942:Organometallic Compounds; D011725:Pyridines; D011744:Pyrimidinones; D013438:Sulfhydryl Compounds; C000613706:pyridine-2-thiol; C063633:cobalt phthalocyanine
Aggregation; Characterization; Complexation; Metallophthalocyanine derivatives; Phthalocyanine