Synthesis and antimicrobial activity of N-(4-chlorophenyl)-β-alanine derivatives with an azole moiety

Anusevičius, Kazimieras; Jonuškienė, Ilona; Mickevičius, Vytautas

doi:10.1007/s00706-013-1074-8

Cited by 13 publications

(8 citation statements)

References 18 publications

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“…N -Aryl-β-alanines and their esters, upon treatment with carbamide or potassium/sodium thiocyanates in acidic medium, form the N-substituted ureido and thioureido acids which undergo facile cyclization to the corresponding hexahydropyrimidine derivatives [27,28]. Thus, β-alanine 3 was transformed to 4-(2,4-dioxo-1,3-diazinan-1-yl)benzene-1-sulfonamide ( 5 ) and the corresponding thio analogue 6 .…”

Section: Resultsmentioning

confidence: 99%

“…The formation of dihydropyrimidinedione and dihydropyrimidinonethione rings in compounds 5 and 6 has been determined by the presence of the NH group proton singlets at 10.52 ppm for the oxo derivatives and 11.42 ppm for the thio derivatives in the corresponding 1 H-NMR spectra. Carboxyhydrazides are convenient precursors for the synthesis of heterocyclic compounds [27,28,29,30,31,32]. In the reaction with hydrazine, carboxylic acid esters form hydrazides much easier than acids themselves.…”

Section: Resultsmentioning

confidence: 99%

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4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases

et al. 2014

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A series of N-aryl-β-alanine derivatives and diazobenzenesulfonamides containing aliphatic rings were designed, synthesized, and their binding to carbonic anhydrases (CA) I, II, VI, VII, XII, and XIII was studied by the fluorescent thermal shift assay and isothermal titration calorimetry. The results showed that 4-substituted diazobenzenesulfonamides were more potent CA binders than N-aryl-β-alanine derivatives. Most of the N-aryl-β-alanine derivatives showed better affinity for CA II while diazobenzenesulfonamides possessed OPEN ACCESSMolecules 2014, 19 17357 nanomolar affinities towards CA I isozyme. X-ray crystallographic structures showed the modes of binding of both compound groups.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases

et al. 2014

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“…They are perfect precursors for the synthesis of four-membered [1][2][3], five-membered [4], six-membered [5][6][7][8][9][10][11], and seven-membered [12,13] heterocycles possessing valuable practical properties. Oxohydropyridines, one class of the cyclization products of N-substituted b-amino acids, are very important intermediates in the synthesis of a large number of biologically active heterocyclic compounds [14,15].…”

Section: Introductionmentioning

confidence: 99%

Unexpected transformation of ethyl 1-(4-chlorophenyl)-2-methyl-4-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate and antibacterial activity of the products

et al. 2014

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The cyclization reaction of N-(4-chlorophenyl)-b-alanine, in the presence of piperidine as a catalyst, provided ethyl 1-(4-chlorophenyl)-2-methyl-4-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate, which reactions with different hydrazines were carried out resulting in formation of a variety of tetrahydropyridine, dihydropyrazolone, and oxazole derivatives in good yields. 5-[2-[(4-Chlorophenyl) amino]ethyl]-4-(1-hydrazinylethylidene)-2,4-dihydro-3H-pyrazol-3-one was converted into a series of hydrazones, which provided tetrahydro-3H-pyrazolo[4,3-c]pyridin-3-one under treatment with acids. The structures of all synthesized compounds were confirmed by IR, 1 H NMR, and 13 C NMR spectroscopy. The structures of three compounds were unambiguously assigned by means of X-ray analysis data. Some of the synthesized compounds exhibited weak antibacterial activity.

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“…Amino acids, their derivatives and products of their cyclization are important in the synthesis of biologically active compounds, for example pharmaceuticals, protecting agents of field plants and plant regulators. N Substituted B-alanine have been widely studied for many different purposes because of their biological activity, for example as growth stimulators of agricultural crops (1), (2) (8) , Amino acids play central roles both as building blocks of proteins and as intermediates in metabolism. They are classified as essential and non-essential amino acids, which is an amino acid in which the amino group is attached to the β-carbon (the carbon two atoms away from the carboxylate group) instead of the more usual αcarbon for alanine (α-alanine).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and spectroscopic study of new ligand 3-(acetylthioureido)propanoic acid with their metal complexes

Kader

Sarhan

2022

ijhs

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A new ligand 3-(3-acetylthioureido)propanoic acid (ATA) was prepared through the reaction of acetyl chloride, ammonium thiocyanate and b- alanine. For this study the following methods were used: FT-IR, 1H-NMR 13C-NMR spectra and the Elemental analysis. complexesis of M+2=Mn,Cu,Ni,Co,Zn,Cd and Hg derived from3-(3-acetylthioureido) propanoic acid have been synthesized and characterized by elemental analyses, molar conductance, magnetic suscpility, FT-IR, UV Vis spectra, The results have shown complexation with b-alanine derivative with metal ion in a 1:2 ratio. The spectral characterization confirms the formation of ligand and complexes. The evidences from the above results suggest the ligand to be abi dentate ion.

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Synthesis and antimicrobial activity of N-(4-chlorophenyl)-β-alanine derivatives with an azole moiety

Cited by 13 publications

References 18 publications

4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases

4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases

Unexpected transformation of ethyl 1-(4-chlorophenyl)-2-methyl-4-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate and antibacterial activity of the products

Synthesis and spectroscopic study of new ligand 3-(acetylthioureido)propanoic acid with their metal complexes

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