Synthesis and antimicrobial activity of copper(ii) non-electrolyte compounds containing imidazole and condensation products of α-amino acids with salicylaldehyde and its derivatives
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2023-05-11 03:25
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GULYA, Aurelian, LOZAN-TYRSHU, K., TSAPKOV, Victor I., RUDIK, V.. Synthesis and antimicrobial activity of copper(ii) non-electrolyte compounds containing imidazole and condensation products of α-amino acids with salicylaldehyde and its derivatives. In: Биологически активные вещества и материалы: фундаментальные и прикладные вопросы получения и применения, Тезисы, 23-28 mai 2011, Kiev. Новый Свет: ФОП Бровко А.А., 2011, p. 44. ISBN 978-966-96879-6-8.
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Биологически активные вещества и материалы: фундаментальные и прикладные вопросы получения и применения, Тезисы 2011
Conferința "Биологически активные вещества и материалы: фундаментальные и прикладные вопросы получения и применения, Тезисы"
Kiev, Ucraina, 23-28 mai 2011

Synthesis and antimicrobial activity of copper(ii) non-electrolyte compounds containing imidazole and condensation products of α-amino acids with salicylaldehyde and its derivatives


Pag. 44-44

Gulya Aurelian1, Lozan-Tyrshu K.2, Tsapkov Victor I.1, Rudik V.2
 
1 Moldova State University,
2 ”Nicolae Testemițanu” State University of Medicine and Pharmacy
 
 
Disponibil în IBN: 29 septembrie 2022



Teza

Amino acids derivatives have a wide range of donor atoms and form with metal ions coordination compounds of various composition and properties. The structure and physicochemical properties of these complexes are determined by the nature of the central atom and ligands. However, since mainly salicylaldehyde and glycine were used as initial substances in the complexes synthesis, it was interesting to find out how the introduction of various substituents and such amine as imidazole in the composition of condensation products will affect the composition, structure and properties of these compounds. The aim of the given work is to find optimum conditions of synthesis, to determine the structure, to study the physicochemical and antimicrobial properties of copper(II) non-electrolyte compounds containing imidazole (Im) and the condensation products (H2L1-9) of glycine, alanine and phenylalanine with salicylic (HL1, H2L7, H2L8), 5- bromo-(H2L2), 5-nitro-(H2L3), 2-hydroxy-1-naphthoic (HL9) aldehydes and 2,5-(HL4), 2,4-(HL5), 2,3-(HL6) dihydroxy-benzaldehydes. N OH O R3 R2 R1 R4 OH H2L1-8 = H2L9 = N OH O OH ; ; NH Im =N H2L1 : R1 = R2 = R3 = R4 = H; H2L2 : R1 = Br, R2 = R3 = R4 = H; H2L3 : R1 = NO2, R2 = R3 = R4 = H; H2L4 : R1 = OH, R2 = R3 = R4 = H; H2L5 : R1 = R3 = R4 = H; R2 = OH; H2L6 : R1 = R2 = R4 = H, R3 = OH; H2L7 : R1 = R2 = R3 = H, R4 = CH3; H2L8 : R1 = R2 = R3 = H, R4 = CH2C6H5 . The experiment has shown that by the interaction of hot (50-55°) ethanolic solutions of glycine, alanine and phenylalanine with salicylaldehyde or its substitutents mentioned above, imidazole (Im) and copper acetate, taken in the molar ratio of 1:1:1:1, microcrystalline substances are obtained (I-IX). By means of the elemental analysis data the following composition has been proposed for these substances: Cu(Im)(L1-9) . nH2O [H2L1-9 = H2L1(I), H2L2(II), H2L3(III), H2L4(IV), H2L5(V), H2L6(VI), H2L7(VII), H2L8(VIII), H2L9(IX), n = 0-2]. By means of the data of Xray analysis of the compound I, magnetochemical, IR spectroscopic and thermogravimetric study of the other substances it has been established that the synthesized coordination compounds form polymer chains with the help of the bridging azomethine carboxyl groups. In these complexes the coordination polyhedron of the copper atom is a distorted tetragonal pyramid. Its base is formed by the phenolic and carboxylic oxygen atoms and also by the azomethinic nitrogen of the condensation product and imidazole. The oxygen atom of the carboxyl group of the neighbouring complex occupies the apical vertex of the coordination pyramid of the first copper central atom. The azomethines Н2L1-9 behave as double deprotonated O,N,O tridentate ligands with bridging carboxyl groups. The thermolysis of the complexes occurs through the stage of complete thermal decomposition (360-530оС). The antimicrobial activity has been studied “in vitro” under liquid nutritive environment (peptonate bullion, pH = 7.0) by means of successive dilutions method. It has been established that the synthesized compounds display selective bacteriostatic and bactericide activity. The antimicrobial activity towards Gram-positive bacteria (Staphylococcus aureus, ATCC 25923 and Bacillus cereus ГИСК 8035) is displayed in the concentration range 75-300 μg/mL. The investigated coordination compounds are less effective for the proliferation of Gram-negative test cultures (Escherichia coli ATCC 25922, Shigela sonnei and Salmonella abony ГИСК 03/03): their minimum inhibitory concentration (MIC) and minimum bactericide concentration (MBC) are displayed in the concentration range 150-300 μg/mL. The experiment has shown that MIC and MBC of the compounds I-IX are influenced by the substituents nature (R1-4) in the azomethines Н2L1-9 and change as follows: NO2 > Br » OH. In addition, the replacement of the salicylaldehyde with the naphtalydene fragment in the coordinated azomethine reduces the antimicrobial activity of the complex.