ABSTRACT
Spired by the chemical structure of Cilostazol, a selective phosphodiesterase 3A (PDE3A) inhibitor, several novel hybrid compounds of nucleobases (uracil, 6-azauracil, 2-thiuracil, adenine, guanine, theophylline and theobromine) and tetrazole were designed and successfully synthesized and their inhibitory effects on PDE3A as well as their cytotoxicity on HeLa and MCF-7 cancerous cell lines were studied. Obtained results show the linear correlation between the inhibitory effect of synthesized compounds and their cytotoxicity. In some cases, the PDE3A inhibitory effects of synthesized compounds are higher than the Cilostazol. Besides, compared to a standard anticancer drug methotrexate, some of the synthesized compounds showed the higher cytotoxicity against the HeLa and MCF-7 cancerous cell lines.
Subject(s)
Antineoplastic Agents/chemical synthesis , Cyclic Nucleotide Phosphodiesterases, Type 3/metabolism , Nucleotides/chemistry , Phosphodiesterase 3 Inhibitors/chemistry , Tetrazoles/chemistry , Antineoplastic Agents/metabolism , Antineoplastic Agents/pharmacology , Binding Sites , Cell Line, Tumor , Cell Survival/drug effects , Cyclic Nucleotide Phosphodiesterases, Type 3/chemistry , Humans , Kinetics , Molecular Docking Simulation , Phosphodiesterase 3 Inhibitors/metabolism , Quinolones/chemistry , Structure-Activity RelationshipABSTRACT
In the current study, glycerol was successfully employed as a nonvolatile, non-toxic, non-flammable, biodegradable, very cheap, easily accessible, and efficient reaction medium for the microwave-enhanced diastereoselective synthesis of 2-(N-carbamoylacetamide)-substituted 2,3-dihydrothiophenes via a catalyst-free one-pot four-component reaction. A versatile range of starting materials were used, and diverse products were obtained in good to excellent yields and very short reaction times. Moreover, the reaction medium was recovered and reused several times without any loss of the efficiency.
Subject(s)
Acetamides/chemistry , Microwaves , Thiophenes/chemistry , Thiophenes/chemical synthesis , Triglycerides/chemistry , Chemistry Techniques, Synthetic , Kinetics , StereoisomerismABSTRACT
γ-Spiroiminolactone derivatives can be synthesized through an one-pot three-component reaction of cyclic carbonyl compounds (isatin, acenaphthoquinone, ninhydrin), activated α-methylene carbonyl groups and isocyanides in water using sodium dodecyl sulfate (SDS) as a commercially available and cheap surfactant compound. All products were obtained in good to excellent yields without formation of any by-products in water as a green and benign reaction medium. Moreover, presented method was successfully applied for the synthesis of some novel bis(spiroiminolactone) derivatives.
ABSTRACT
CaCl(2) is applied as an efficient reusable and eco-friendly bifunctional catalyst for the one-pot three-component synthesis of 4H-pyrans under ultrasonic irradiation. A broad range of substrates including the aromatic and heteroaromatic aldehydes, indoline-2,3-dione (isatin) derivatives, acenaphthylene-1,2-dione (acenaphthenequinone) and 2, 2-dihydroxy-2H-indene-1,3-dione (ninhydrin) were condensed with carbonyl compounds possessing a reactive α-methylene group and alkylmalonates. All reactions are completed in short times, and the products are obtained in good to excellent yields. The catalyst could be recycled and reused several times without any loss of efficiency.
Subject(s)
Anti-Bacterial Agents/chemical synthesis , Calcium Chloride/chemistry , Pyrans/chemical synthesis , Ultrasonics , Acenaphthenes/chemical synthesis , Aldehydes/chemical synthesis , Catalysis , Isatin/chemical synthesis , Molecular Structure , Ninhydrin/chemical synthesis , RadiationABSTRACT
A catalyst-free one-pot four component methodology for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under ultrasonic irradiation at room temperature using 1-butyl-3-methylimidazolium bromide, [Bmim]Br, as a neutral reaction medium is described. A broad range of structurally diverse aldehydes (aromatic aldehydes bearing electron withdrawing and/or electron releasing groups as well as heteroaromatic aldehydes) were applied successfully, and corresponding products were obtained in good to excellent yields without any byproduct.
Subject(s)
Chemistry Techniques, Synthetic/methods , Imidazoles/chemistry , Ionic Liquids/chemistry , Phthalazines/chemistry , Phthalazines/chemical synthesis , Ultrasonics , TemperatureABSTRACT
A catalyst-free one-pot four component methodology for the synthesis of 1,2,4,5-substituted imidazoles under conventional heating and microwave irradiation using 1-butyl-3-methylimidazolium bromide, [Bmim]Br, as a neutral reaction media is described. A broad range of structurally diverse aldehydes (aromatic aldehydes bearing electron withdrawing and/or electron releasing groups as well as heteroaromatic aldehydes) and primary amines (aromatic and aliphatic) were applied successfully, and corresponding products were obtained in good to excellent yields without any byproduct.
