ChemInform Abstract: Synthesis and Antifungal Activity Evaluation of 3‐Hydroxyimidazo(1,2‐a) pyridine and 3‐Hydroxyimidazo(1,2‐a)pyrimidine Derivatives.
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“…However, a large number of strains have shown resistance to azoles [ 18 , 19 , 20 ], making it necessary to seek alternatives for treatment of fungal infections. Although there are reports on the application of imidazo[1,2- a ]pyrimidine derivatives as antifungal agents [ 21 , 22 ], they still do not display the pharmacological profile sought. Hence, it is necessary to design and synthesize new compounds with a better pharmacological profile.…”
A series of 3-benzoyl imidazo[1,2-a]pyrimidines, obtained from N-heteroarylformamidines in good yields, was tested in silico and in vitro for binding and inhibition of seven Candida species (Candida albicans (ATCC 10231), Candida dubliniensis (CD36), Candida glabrata (CBS138), Candida guilliermondii (ATCC 6260), Candida kefyr, Candida krusei (ATCC 6358) and Candida tropicalis (MYA-3404)). To predict binding mode and energy, each compound was docked in the active site of the lanosterol 14α-demethylase enzyme (CYP51), essential for fungal growth of Candida species. Antimycotic activity was evaluated as the 50% minimum inhibitory concentration (MIC50) for the test compounds and two reference drugs, ketoconazole and fluconazole. All test compounds had a better binding energy (range: −6.11 to −9.43 kcal/mol) than that found for the reference drugs (range: 48.93 to −6.16 kcal/mol). In general, the test compounds showed greater inhibitory activity of yeast growth than the reference drugs. Compounds 4j and 4f were the most active, indicating an important role in biological activity for the benzene ring with electron-withdrawing substituents. These compounds show the best MIC50 against C. guilliermondii and C. glabrata, respectively. The current findings suggest that the 3-benzoyl imidazo[1,2-a]pyrimidine derivatives, herein synthesized by an accessible methodology, are potential antifungal drugs.
“…However, a large number of strains have shown resistance to azoles [ 18 , 19 , 20 ], making it necessary to seek alternatives for treatment of fungal infections. Although there are reports on the application of imidazo[1,2- a ]pyrimidine derivatives as antifungal agents [ 21 , 22 ], they still do not display the pharmacological profile sought. Hence, it is necessary to design and synthesize new compounds with a better pharmacological profile.…”
A series of 3-benzoyl imidazo[1,2-a]pyrimidines, obtained from N-heteroarylformamidines in good yields, was tested in silico and in vitro for binding and inhibition of seven Candida species (Candida albicans (ATCC 10231), Candida dubliniensis (CD36), Candida glabrata (CBS138), Candida guilliermondii (ATCC 6260), Candida kefyr, Candida krusei (ATCC 6358) and Candida tropicalis (MYA-3404)). To predict binding mode and energy, each compound was docked in the active site of the lanosterol 14α-demethylase enzyme (CYP51), essential for fungal growth of Candida species. Antimycotic activity was evaluated as the 50% minimum inhibitory concentration (MIC50) for the test compounds and two reference drugs, ketoconazole and fluconazole. All test compounds had a better binding energy (range: −6.11 to −9.43 kcal/mol) than that found for the reference drugs (range: 48.93 to −6.16 kcal/mol). In general, the test compounds showed greater inhibitory activity of yeast growth than the reference drugs. Compounds 4j and 4f were the most active, indicating an important role in biological activity for the benzene ring with electron-withdrawing substituents. These compounds show the best MIC50 against C. guilliermondii and C. glabrata, respectively. The current findings suggest that the 3-benzoyl imidazo[1,2-a]pyrimidine derivatives, herein synthesized by an accessible methodology, are potential antifungal drugs.
“…Reaction of EMCA with 4,5-dihydro-1 H -imidazol-2-amines leads to 2,3-dihydroimidazo[1,2- a ]pyrimidines [ 1 – 4 ] and represents one of the synthetic methods of this heterocyclic system by reaction of imidazol-2-amine derivatives with electrophilic compounds (the main alternative involves the imidazole ring closure by condensation of pyrimidin-2-amines with an appropriate compound) [ 5 ]. The imidazo[1,2- a ]pyrimidine system is present in many biologically active compounds which have been reported to exhibit anti-inflammatory and analgesic [ 6 – 9 ], antibacterial [ 10 – 14 ], antiviral [ 15 ], antifungal [ 16 , 17 ], insectidal, acaricidal, and nematocidal [ 18 ], central nervous system (CNS) [ 19 – 23 ], hormonal [ 24 ], mutagenic [ 25 ], anticancer [ 26 , 27 ], and cardiovascular [ 28 ] activity. …”
The pseudo-Michael reaction of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl 2-cyano-3-methoxyprop-2-enoate (ethyl ethoxymethylenecyanoacetate) is investigated. At −10 °C reaction takes place on the exocyclic nitrogen atom, giving exclusively ethyl esters of 2-cyano-3-[(1-phenyl-4,5-dihydro-1H-imidazol-2-yl)amino]prop-2-enoic acid. The formation of isomeric enamines which may be a theoretical product of the reaction on N3 ring nitrogen atom is not observed. The N6 enamines, heated in boiling acetic acid, yield cyclic 1-aryl-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles. Heating of the enamines to the temperature of 120–140 °C without a solvent makes it possible to obtain a mixture of 1-aryl-5-oxo-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles and ethyl 1-aryl-5-imino-2,3-dihydroimidazo[1,2-a]pyrimidine-6-carboxylates. The reaction of the respective hydrobromides of 1-aryl-4,5-dihydro-1H-imidazol-2-amines with ethyl ethoxymethylenecyanoacetate in the presence of triethylamine gives selectively 1-aryl-5-oxo-1,2,3,5-dihydroimidazo[1,2-a]pyrimidine-6-carbonitriles.Graphical Abstract
“…This methodology afforded the C -3 position functionalized imidazopyridines due to its nucleophilicity. The pharmacological activities of these heterocycles are dependent on the nature of the substituent on the imidazo ring. , Among them, structures related to imidazo[1,2- a ]pyridin-3-ol with 2-aryl substituents are biologically active with both antifungal and anthelmintic activity. , Unfortunately, very limited procedures have been developed to make such compounds with special properties . Actually, there is still no catalytic, efficient, green method for synthesis of C -3 oxo-substituted imidazo[1,2- a ]pyridines (Scheme , eqs 2 and 3).…”
A catalytic oxidative cyclization of 2-aminopyridines or 2-aminobenzothiazole with 2-phenoxyacetophenones (a kind of lignin platform compound) was developed, efficiently providing valuable 3-phenoxy imidazo[1,2-a]pyridines or 3-phenoxy benzo[d]imidazo[2,1-b]thiazoles. The reaction was realized under oxygen by simply using inexpensive CuI as the catalyst.
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