scholarly journals Synthesis, physic and chemical properties of 2-(4-R-5-(thiophene-2-ylmethyl)-4h-1,2,4-triazole-3-ylthio)acetate acids and their salts

2018 ◽  
pp. 48-54
Author(s):  
O. A. Suhak ◽  
О. I. Panasenko ◽  
Ye. G. Knysh
Keyword(s):  
Biological Activity ◽  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Chemical Properties ◽  
Biological Action ◽  
Biologically Active ◽  
Physico Chemical ◽  
Methods Of Synthesis ◽  
Medicinal Drugs

Derivatives of 1,2,4-triazole are inherent in various types of biological activity. They can be used as pesticide and medicinal drugs (anticonvulsants, analgetics, antitumor and antibacterial). In this regard the search of new methods of synthesis and investigation of biological activity of 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acids and their salts is relevant nowadays. With the aim of finding the new biologically active compounds 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acids and their salts are synthesized, where R is methyl, ethyl, phenyl. The interaction of 4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-thions with monochloracetate acid in the medium of i-propyl alcohol in the presence of an equivalent amount of alkali the corresponding 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4 triazole-3-ylthio)acetate acids are obtained on the basis of which the corresponding salts of morpholine, dimethylamine, monoethanolamine, pteridine, ZnSO4 , CuSO4, NaOH and KOH are obtained and the structure of the received compounds was confirmed on the basis of the data of elemental, IR-, 1H-NMR-spectroscopy. The synthesis of 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio) acetate acids and their salts was conducted. With the help of modern physico-chemical methods: elemental analysis, IR, 1H-NMR-spectroscopy the structure of synthesized compounds, and their individuality by HPLC-MS is proved. In the IR spectrum of the compound 2-(4-phenyl-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acid Ic available band fluctuations groups characteristic for the nucleus of 1,2,4-triazole: NH– in the range of 3 400–3 100 cm-1,–C=N– – 1 690–1 620 cm-1. Also present band fluctuations groups –C–S– at 691 cm-1. Available band fluctuations characteristic of the group –CH2 within 1496.59 cm-1 and group –COO-H– – 1722.70 cm-1. This suggests the possibility to further study the biological action of the synthesized compounds.

scholarly journals Synthesis and properties of 1-aminocarbonylmethyl-5-aryl- 4-aroyl-3-hydroxy-3-pyrroline-2-ones

2020 ◽  
Vol 64 (10) ◽  
pp. 28-32
Author(s):  
Vladimir L. Gein ◽  
◽  
Evgenia V. Pastukhova ◽  
Keyword(s):  
Acetic Acid ◽  
Nmr Spectroscopy ◽  
Physicochemical Properties ◽  
Hydrazine Hydrate ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Glacial Acetic Acid ◽  
Spectral Characteristics ◽  
Biologically Active ◽  
Three Component Reaction

3-Hydroxy-3-pyrrolin-2-ones are fully hydrogenated heterocyclic compounds, the base of which is included in a number of biologically active substances and drugs. Scientists' interest in 3-Hydroxy-3-pyrrolin-2-ones is due to the fact that, with their availability and high stability, they also have high reactivity due to the active carbonyl group in the third position of the heterocycle and easily interact with moconucleophiles. In addition, the presence of acyl and ethoxycarbonyl groups in the fourth position of the heterocycle makes it possible to obtain various condensed systems in reactions with binucleophiles, thereby making it possible to expand the range of the indicated compounds. We set the task to prepare 5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones containing an amino-carbonylmethyl substituent in the first position of the heterocycle, which were not previously described in the literature. It was also supposed to establish how the obtained compounds react with hydrazine hydrate. A series of 1-aminocarbonylmethyl-5-aryl-4-aroyl-3-hydroxy-3-pyrrolin-2-ones was obtained by setting up a three-component reaction of aroylpyruvic acid methyl ester with aromatic aldehydes and glycinamide hydrochloride in glacial acetic acid. The structure of the obtained compounds was established on the basis of IR and 1H NMR spectroscopy data. Based on the data of 1H NMR spectroscopy and a positive reaction with an alcoholic solution of iron(III) chloride, the predominant existence of the obtained compounds in the enol form was established. The article describes the mechanism of three-component reactions, the structural formulas of the obtained compounds, their physicochemical properties and spectral characteristics, as well as the yields of the reaction products. We have also studied the interaction of 1-substituted 5-aryl-4-acyl-3-hydroxy-3-pyrrolin- 2-ones with such a binucleophilic reagent as hydrazine hydrate. As a result of refluxing 1-amino-carbonylmethyl-3-hydroxy-4-(4-methoxybenzoyl)-5-(2-chlorophenyl)-3-pyrrolin-2-one and hydrazine hydrate in glacial acetic acid, 2-[4-(2-chlorophenyl)-3-(4-methoxyphenyl)-6-oxo-4,6-dihydropyrrolo [3,4-c] pyrazol-5(1H)-yl] acetamide. The article describes the proposed reaction mechanism, product yield, its physicochemical properties and spectral characteristics.

Synthesis of new photobactericidal polymers by “click chemistry” and a study of their biological activity

e-Polymers ◽  
2012 ◽  
Vol 12 (1) ◽  
Author(s):  
Abdelmajid Memmi ◽  
Robert Granet ◽  
Mahjoub Aouni ◽  
Amina Bakhrouf ◽  
Pierre Krausz
Keyword(s):  
Biological Activity ◽  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Addition Reaction ◽  
Fatty Ester ◽  
E Coli ◽  
Plastic Materials ◽  
Covalently Linked ◽  
High Yields

AbstractPhotobactericidal plastic materials have been synthesized from cellulose and natural or synthetic porphyrins. The photosensitizer was covalently linked to a cellulose fatty ester by means of a Huisgen cyclo addition reaction resulting in high yields and degrees of substitution (DS). The polymers obtained were characterized by UV vis., IR and 1H NMR spectroscopy. Photobactericidal properties were evaluated on the three pathogenic strains E. coli, S. aureus and P. aeruginosa. A total killing of the bacteria was achieved with plastics with DS values higher than 1% upon illumination.

scholarly journals Synthesis of new 3-(2-aminothiazol-4-yl)-4-hydroxy-2H-chromen-2-one derivatives

2006 ◽  
Vol 71 (6) ◽  
pp. 581-585 ◽  
Author(s):  
S. Sukdolak ◽  
N. Vukovic ◽  
S. Solujic ◽  
M. Milosev ◽  
N. Manojlovic ◽  
...  
Keyword(s):  
Biological Activity ◽  
Nmr Spectroscopy ◽  
Structural Analysis ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Chemical Structure ◽  
High Yield ◽  
Thiourea Derivatives ◽  
Starting Compound ◽  
Derivatives Of

Aminothiazole derivatives of 4-hydroxy-2H-chromen-2-one were prepared by the Hantzsch reaction1 using 3-(2-bromoacetyl)-4-hydroxy-2H-chromen-2-one and thiourea derivatives. Starting compound for this synthesis 3-(2-bromoacetyl)-4-hydroxy- 2H-chromen-2-one (1) was prepared previously.2 Also, for this synthesis we used thiourea derivatives (2a-j) as compounds which possess groups with biological activity. Reactions are carried out in refluxing ethanol for a period of 30 - 45 min. Final products (3a-j) are obtained in a high yield. Chemical structure of the obtained compounds was confirmed by elemental and structural analysis (IR and 1H NMR spectroscopy).

scholarly journals Direct CH/CH functionalization of 1,3-dihydroxy-9H-xanthen-9-one and 1,3-dimethoxy-9H-xanthen-9-one with 1,2,4-triazines and quinazoline

2020 ◽  
Vol 7 (4) ◽  
pp. 233-236
Author(s):  
A. D. Sharapov ◽  
R. F. Fatykhov ◽  
I. A. Khalymbadzha ◽  
O. N. Chupakhin
Keyword(s):  
Biological Activity ◽  
Nmr Spectroscopy ◽  
Nucleophilic Substitution ◽  
1H Nmr ◽  
Nucleophilic Addition ◽  
1H Nmr Spectroscopy ◽  
Wide Spectrum ◽  
Oxidation Products ◽  
Nucleophilic Substitution Of Hydrogen ◽  
Dehydrogenative Coupling

An electron-deficient series of 1,2,4-triazines and quinazoline have been used for cross-dehydrogenative coupling with 1,3-dihydroxy and 1,3-dimethoxyxanthones to give stable nucleophilic addition products. The adducts and their subsequent oxidation products were obtained in good yields and the structures of the compounds were confirmed by 1H NMR spectroscopy. These results expand the scope of the methodology of nucleophilic substitution of hydrogen with the participation of xanthones with azines. Moreover, this methodology makes it possible to obtain new organic materials based on xanthones, which have a wide spectrum of biological activity.

scholarly journals Synthesis of 5-aryl-4-acyl-3-hydroxy- 1-carboxymethyl-3-pyrrolin-2-ones

2020 ◽  
Vol 64 (11) ◽  
pp. 9-12
Author(s):  
Vladimir L. Gein ◽  
◽  
Evgenia V. Pastukhova ◽  
Keyword(s):  
Nmr Spectroscopy ◽  
Carbonyl Group ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Spectral Characteristics ◽  
Alcoholic Solution ◽  
Biologically Active ◽  
Acyl Residue ◽  
Reaction Products ◽  
Three Component Reaction

5-Aryl-1,4-disubstituted terahydropyrrole-2,3-diones are five-membered nitrogen heterocycles containing in the first alkyl position or an aryl functionalized substituent and in the fourth position in another state of nature an acyl residue. Trahydropyrrole-2,3-diones constitute a significant class of available and stable substances. Along with this, they easily enter into reactions with various nucleophilic reagents due to the highly reactive carbonyl group in the third position of the heterocycle. The presence of the latter, as well as the carbonyl group of the side chain, makes it possible to form various condensed systems from heterocycles in reactions with binucleophilic reagents. The synthesis of biologically active substances based on 1,4,5-trisubstituted tetrahydropyrrole-2,3-diones is one of the promising ways of using this class of compounds. Previously, it was found that 1,4,5-trisubstituted 3-hydroxy-3-pyrin-2-ones have anti-inflammatory, analgesic, antimicrobial, nootropic, antiplatelet and antiviral activity. We set the task to obtain 5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones, in the first position of the heterocycle there is a carboxymethyl substituent. By setting up a three-component reaction of acylpyruvic acid ether with aromatic aldehydes and glycine in dioxane in dioxane. The structure of the compound was established on the basis of IR and 1H NMR spectroscopy data. Based on the data of 1H NMR spectroscopy and a positive reaction with an alcoholic solution of iron(III) chloride, the predominant presence of compounds in the enol form was established. The article presents the proposed mechanism and schemes of the formula for the synthesis of 5-aryl-4-acyl-3-hydroxy-1-carboxymethyl-3-pyrrolin-2-ones, their physicochemical and spectral characteristics, as well as the yields of the reaction products.

scholarly journals Identification and Quantitation of Ursolic and Oleanolic Acids in Ilex aquifolium L. Leaf Extracts Using 13C and 1H-NMR Spectroscopy

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4413
Author(s):  
Doreen Palu ◽  
Ange Bighelli ◽  
Joseph Casanova ◽  
Mathieu Paoli
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
13C Nmr ◽  
1H Nmr Spectroscopy ◽  
Limit Of Detection ◽  
Biologically Active ◽  
Leaf Extracts ◽  
Simple Method ◽  
Ilex Aquifolium ◽  
Limit Of Quantitation

Leaves of Ilex aquifolium L. have been used for their therapeutic properties. In previous studies, components contained in the leaves were first isolated by various chromatographic techniques. Then, quantitation of oleanolic and ursolic acids, which are responsible for the biological and therapeutic activities of the plant, was performed by HPLC, HPTLC, and somewhat by GC-MS. Our objective was to develop a simple method that allows the identification of compounds contained in the leaves of Corsican I. aquifolium and to quantify ursolic and oleanolic acids. Leaves were successively extracted with hexane and dichloromethane. The extracts were chromatographed on silica gel and the fractions of column chromatography submitted to 13C-NMR analysis, following a computerized method developed in the laboratory. 13C-NMR allowed the identification of various triterpenes including ursolic acid and oleanolic acid. Quantitation of both acids was achieved, for the first time, by 1H-NMR after validation of the method (accuracy, precision, linearity, limit of detection and limit of quantitation). Ursolic and oleanolic acids accounted for 55.3% and 20.8% of the dichloromethane extract, respectively. This represents 1.3% and 0.5% of the mass of dried leaves. 1H-NMR spectroscopy appeared as a powerful tool for a rapid quantitation of biologically active compounds from I. aquifolium.

Preparation of copper pectate preparation for use in medical practice

2021 ◽  
Author(s):  
L.A. Mikheeva ◽  
S.A. Shchelkaev ◽  
A.V. Mikheeva
Keyword(s):  
Complex Formation ◽  
Metal Complexes ◽  
Human Body ◽  
Structural Parameters ◽  
Chemical Properties ◽  
Biologically Active ◽  
Physico Chemical ◽  
Methods Of Synthesis ◽  
Negative Effect ◽  
Pectin Substances

Currently, the processes of complexation of various ligands, including biopolymers with metals, attract the attention of scientists from different countries not only in order to obtain new data on the methods of synthesis and properties of metal complexes, but also in connection with the search for ways to obtain new effective biologically active drugs among them. Since the life around us is oversaturated with various artificially produced drugs that have a negative effect on the human body, today, more than ever before, the question arises of using natural, environmentally friendly ingredients instead of synthetic ones, for example, such as pectin. The study of the structural parameters and physico-chemical properties of complexes of pectin substances with metals will significantly expand the scope of their practical use. Key words: metal complexes, pectin, copper pectate, complex formation.

scholarly journals Synthesis and characterization of some heterocyclic including oxazoles,Thiazoles, Pyridazines, phthalizines and Pyrazoles with evaluating of biological activity.

2013 ◽  
Vol 10 (3) ◽  
pp. 818-827
Author(s):  
Baghdad Science Journal
Keyword(s):  
Acetic Acid ◽  
Biological Activity ◽  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Acid Hydrazide ◽  
Synthesis And Characterization ◽  
Ft Ir ◽  
New Compounds

A series of new compounds including p-bromo methyl pheno acetate [2]. N-( aminocarbonyl)–p-bromo pheno acetamide [3] , N-( aminothioyl) -p-bromo phenoacetyl amide [4], N-[4-(p-di phenyl)-1,3-oxazol-2-yl]-p-bromopheno acetamide [5],N-[4-p-di phenyl]-1,3-thiazol-2-yl-p-bromo phenoacet amide [6], p-bromopheno acetic acid hydrazide [7] , 1-N-(p-bromo pheno acetyl)-1,2-dihydro-pyridazin-3,6- dione [8], 1-N-(p-bromo pheno acetyl)-1,2-dihydro-phthalazin-3,8- dione[ 9], 1-(p-bromo pheno acetyl)-3-methylpyrazol-5-one [10] and 1-(p-bromo phenol acetyl)- 3,5-dimethyl pyrazole [11] have been synthesized. The prepared compounds were characterized by m.p.,FT-IR and 1H-NMR spectroscopy. Also ,the biological activity was evaluated .

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