- Synthesis, molecular docking, and antimycotic evaluation of some 3-acyl imidazo[1,2-a]pyrimidines
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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.
- Gómez-García, Omar,Andrade-Pavón, Dulce,Campos-Aldrete, Elena,Ballinas-Indilí, Ricardo,Méndez-Tenorio, Alfonso,Villa-Tanaca, Lourdes,álvarez-Toledano, Cecilio
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- Aminothiazole compound as well as preparation method and application thereof in resisting enterovirus 71
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The invention discloses an aminothiazole compound as well as a preparation method and application thereof in resisting enterovirus 71. The invention belongs to the technical field of medicines. Specifically, 2-chloro-1-(imidazo[1,2-a]pyrimidin-3-yl)ethan-
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Paragraph 0034-0037
(2020/01/03)
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- Kinetic and mechanistic investigations on the oxidation of N'-heteroaryl unsymmetrical formamidines by permanganate in aqueous alkaline medium
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Kinetic studies on the oxidation of two substituted azinyl formamidines (Azn-Fs), namely N,N-dimethyl-N'-(pyrimidin-2-yl) formamidine (Pym-F) and N,N-dimethyl-N'-(pyridin-2-yl) formamidine (Py-F), by alkaline permanganate have been performed by spectrophotometry. The spectroscopic and kinetic evidence reveals the formation of 1:1 intermediate complexes between the oxidant and substrates. The influence of pH on the oxidation rates indicated that the reactions are base-catalyzed. The reactions show identical kinetics, being first order each in [MnO4 -]0 and [Azn-F] 0, but with a fractional first-order dependence on [OH-]. The effect of temperature on the reaction rate has been studied. Increasing ionic strength has no significant effect on the rate. The final oxidation products of Pym-F and Py-F were identified as 2-aminopyrimidine and 2-aminopyridine, respectively, in addition to dimethyl amine and carbon dioxide. Under comparable experimental conditions, the oxidation rate of Py-F is higher than that of Pym-F. A reaction mechanism adequately describing the observed kinetic behavior is proposed, and the reaction constants involved in the different steps of the mechanism have been evaluated. The activation parameters with respect to the rate-limiting step of the reactions, along with thermodynamic quantities, are presented and discussed.
- Fawzy, Ahmed,Shaaban, Mohamed R.
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p. 379 - 386
(2014/05/20)
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- Facile access to novel 3-acylimidazo[1,2-a]pyrimidines under microwave irradiation
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Treatment of mono-, bis- and tris(ω-bromoacetophenone) derivatives with N,N-dimethylformamidine derivative of 2-aminopyrimidine, afforded the novel 3-aroyl or heteroyl derivatives of imidazo[1,2-α]pyrimidine, bis(imidazo[1,2-α]pyrimidine) and tris(imidazo
- Shaaban, Mohamed R.
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p. 1775 - 1783
(2013/09/12)
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- New adenosine receptor ligands and uses thereof
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The present invention provides new compounds with high affinity for adenosine A2A receptors. It also provides antagonists of adenosine A2A receptors and their use as medicaments for the treatment and/or prophylaxis of diseases and di
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Page/Page column 75
(2010/08/07)
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- One-pot synthesis of new imidazo[1,2-a]pyridine and midazo[1,2-a]pyrimidine derivatives
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New imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine derivatives were easily obtained by an one-pot synthesis that implies the reaction of the corresponding 2-aminoheterocycles with N,N-dimethylformamide dimethylacetal (DMFDMA), followed by the reactio
- Georgescu, Florentina,Georgescu, Emilian,Drǎghici, Constantin,Iuhas, Paula C.,Filip, Petru I.
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p. 349 - 352
(2007/10/03)
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- The transformations of 4-heteroarylaminomethylene-5(4H)-oxazolones into dehydropeptide derivatives
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2-Phenyl-4-heteroarylaminomethylene-5(4H)-oxazolones 3, which were prepared from the corresponding N,N-dimethyl-N'-heteroarylformamidines 1 and hippuric acid 2 in acetic anhydride, react with amino acids giving dehydropeptide derivatives 4, 5, and 6 as products. Dehydration of N-protected peptides 7-10, containing glycine at the C-terminal, followed by the reaction with formamidines 1 gave 2-substituted-4-heteroarylaminomethylene-5(4H)-oxazolones 11-14.
- Aljaz-Rozic,Svete,Stanovnik
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p. 1605 - 1611
(2007/10/03)
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- Synthesis of (aryloxy)alkylamines. 2. Novel imidazo-fused heterocycles with calcium channel blocking and local anesthetic activity
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A series of imidazo-fused heterocycles substituted with an (aryloxy)alkylamine side chain were prepared as modifications to butoprozine (I) and found to possess calcium channel blocking activity similar in potency to that of bepridil in trachea smooth mus
- Sanfilippo,Urbanski,Press,Dubinsky,Moore Jr.
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p. 2221 - 2227
(2007/10/02)
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- TRANSFORMATION OF AMINES AND N-HETEROARYLFORMAMIDINES INTO ESTERS OF SUBSTITUTED β-AMINO-α,β-DEHYDRO-α-AMINO ACIDS
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Esters of substituted β-amino-α,β-dehydro-α-amino acids 5 were prepared either by transformation of N-heteroaryl-N,N-dimethylformamidines 2 with 3 into 4, followed by ring opening, or by treatment of primary or secondary amines 1 with 9.
- Stanovnik, Branko,Svete, Jurij,Tisler, Miha,Zorz, Lilijana,Hvala, Ales,Simonic, Igor
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p. 903 - 910
(2007/10/02)
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- Reactions of N-Heteroarylformamide Oximes and N-Heteroarylacetamide Oximes with N,N-Dimethylformamide Dimethyl Acetal. Synthesis of 2-Methyl-s-triazoloazines and N-Methylcyanoaminoazines
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N-Heteroarylformamide oximes 3 (R = H) were converted with N,N-dimethylformamide dimethyl acetal (DMFDMA) into N-heteroaryl-N-methylcyanoamino compounds 5, as the main products.In some instances N-heteroarylcyanoamino compounds 4, cyanoimino compounds 7, and some other products, such as 9 and 10 were also formed.On the other hand, N-heteroarylacetamide oximes 3 (R = CH3) were cyclized under the same reaction conditions into 2-methyl-s-triazoloazines (6).N-Heteroarylacetamide O-methyl oximes 11 and 12 were prepared from the corresponding acetamidines 2 (R = CH3) and O-methylhydroxylamine.
- Stanovnik, Branko,Stimac, Anton,Tisler, Miha,Vercek, Bojan
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p. 577 - 583
(2007/10/02)
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