Synthesis of 3-Hydroxy-1-(p-methoxyphenyl)-2-methylpyridine-4-one and Spectrophotometric Extraction Studies on its Complexation of Vanadium(V)

In this paper a single step synthesis of 3-hydroxy-1-(p-methoxyphenyl)-2-methylpyridine-4-one (HM) using starting maltol and p-anisidine in the presence of acid catalyst (p-toluenesulfonic acid or HCl) is described. The reaction is carried out by heating the aqueous solution of the reactants and a catalyst in a sealed thick-walled glass tube at 150 °C at different reaction times in order to retrieve an optimal yield. The complexation reactions of vanadium(V) with HM as well as the extraction of V(V) from aqueous to organic phase were studied spectrophotometrically. The optimum conditions for extraction of vanadium(V) from aqueous phase, containing chloride or thiocyanate ions, to chloroform solution of HM and complex formation have been evaluated. Based on the results obtained by Job’s and equilibrium shift methods the composition of the complexes has been found to be V(V) : Cl(SCN) : HM = 1:1:2

Synthesis, Crystal and Molecular Structure of Novel Adamantyl Derivatives of N-Aryl Substituted 3-Hydroxy-2-methylpyridine-4-ones

Two novel potentially bioactive compounds, esters 2-methyl-1-phenylpyridine-4-one-3-yl adamantan-1-ylethanoate (1) and 1-(p-methoxyphenyl)-2-methylpyridine-4-one-3-yl adamantan-1-ylethanoate (2), were synthesized by esterification of adamantan-1-ylacetic acid with appropriate N-aryl substituted 3-hydroxypyridine-4-one derivatives. Both compounds are fully characterized using standard spectroscopic methods. Crystal and molecular structures of 1 and 2 were determined by the single crystal X-ray diffraction method. The crystal packing of both 1 and 2 shows separation of the hydrophobic and hydrophilic regions. The crystal structure of 1 is characterized by the two-dimensional hydrogen bonding layers parallel to (001). The crystal packing of 2 is characterized by hydrogen-bonded chains extended in the direction [010].(doi: 10.5562/cca2339

3-Hydroxypyridin-4-ones (Part II): Biological Application as Iron Chelating Agents

Selektivnost prema keliranju trovalentnih kationa metala, u prvom redu Fe(III), osnova je brojnih bioloških učinaka derivata 3-hidroksipiridin-4-ona. Ti spojevi najviše potencijala pokazuju u liječenju oboljenja uslijed kojih dolazi do nakupljanja željeza u organizmu, kao što su razna krvna oboljenja poput talasemije i hemokromatoze te u liječenju neurodegenerativnih bolesti, primjerice Alzheimerove bolesti. Osim deferiprona, koji je već više od 30 godina u kliničkoj upotrebi kao kelator Fe(III), u ovom radu dan je pregled i ostalih najznačajnijih kelatora 3-hidroksipiridin-4-onske strukture s potencijalnom biološkom primjenom. Ovo djelo je dano na korištenje pod licencom Creative Commons Imenovanje 4.0 međunarodna.Selectivity towards trivalent metal cations, especially Fe(III), is the primary basis of a number of 3-hydroxypyridin-4-ones’ biological activities. These compounds have high potential in the treatment of iron overload diseases, in various blood pathologies such as thalassemia and hemochromatosis, as well as in the treatment of neurodegenerative diseases, such as Alzheimer’s disease. Beside deferiprone, the only 3-hydroxypyridin-4-one based iron(III) chelating agent which has been used clinically for more than 30 years, this review will also present other most significant and potentially biologically active chelators with 3-hydroxypyridin-4-one core. This work is licensed under a Creative Commons Attribution 4.0 International License

Synthesis and Biological Activity of Mannose Conjugates with 1-Adamantamine and Ferrocene Amines

Pure α- and β-anomers of O-mannosyl conjugates with 1-adamantamine and ferrocene amines were prepared. The sugar moiety in these glycoconjugates is connected to the amine by a chiral linker (methyl (R)-3-hydroxy-2-methyl propanoate and/or methyl (S)-3-hydroxy-2-methyl propanoate). The α-D-mannopyranosides with adamantane and ferrocene aglycon parts were tested using the hemagglutination assay (inhibition of the agglutination of guinea pig erythrocytes by type 1 fimbriated E. coli HB101 (pPKl4)). All glycoconjugates showed inhibitory potencies in the mM range

An Efficient Synthesis of Novel Adamantane β-Amino Acid: 2-(Adamant-2-yl)-3-aminopropanoic Acid

Novel adamantane-containing β-amino acid, 2-(adamant-2-yl)-3-aminopropanoic acid, interesting from the aspect of medicinal chemistry, was prepared and characterized. It was synthesized in a sequence of three steps with very good overall yield. In the first step ethyl adamant-2-ylidenecyanoacetate was prepared and its crystal structure was determined. Reduction of this unsaturated cyanoacetate by catalytic hydrogenation gave the ethyl ester of the desired amino acid. 2-(Adamant-2-yl)-3-aminopropanoic acid was obtained following ester hydrolysis. (doi: 10.5562/cca2122