Multicomponent hot-water synthesis of 7-unsubstituted 4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines and their antimicrobial and antifungal activity

Komykhov, Sergey A.; Tkachenko, Irina G.; Мусатов, Владимир И.; Diachkov, Mikhail V.; Чебанов, Валентин А.; Десенко, С. М.

doi:10.3998/ark.5550190.p009.610

Cited by 15 publications

(5 citation statements)

References 18 publications

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“…Thus, we selected aliphatic aldehydes, i.e., formaldehyde and acetaldehyde, as the starting material and chose a multicomponent approach to minimize the number of reaction steps according to green chemistry principles as well. Based on our recent research [26–28], where water proved to be an effective solvent for the multicomponent synthesis of low-molecular-mass dihydroazolopyrimidines, we decided to use water also in this case.…”

Section: Resultsmentioning

confidence: 99%

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

Tkachenko

Komykhov

Мусатов

et al. 2019

Beilstein J. Org. Chem.

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The three-component reaction of 5-aminotetrazole with aliphatic aldehydes (formaldehyde, acetaldehyde) and acetoacetic ester derivatives in water under microwave irradiation leads to the selective formation of 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives. Under similar conditions using 4,4,4-trifluoroacetoacetic ester 5-hydroxy-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidines are obtained. The analogous reaction with acetylacetone requires scandium(III) triflate as catalyst. The antioxidant activity of selected compounds was assayed with 1,1-diphenyl-2-picrylhydrazyl.

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Section: Resultsmentioning

confidence: 99%

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

Tkachenko

Komykhov

Мусатов

et al. 2019

Beilstein J. Org. Chem.

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“…Komykhov and co‐authors [157] described the microwave‐assisted “in water” synthesis of drug‐like 7‐unsubstituted 4,7‐dihydro‐1,2,4‐triazolo[1,5 ‐a ]pyrimidines by catalyst‐free three‐component reaction of 3‐amino‐1,2,4‐triazole with paraformaldehyde and various 1,3‐dicarbonyl compounds, such as ethyl and 2‐methoxyethyl acetoacetate, ethyl 3‐oxohexanoate, and acetylacetone. The heterocyclization was regio‐ and position‐selective and gave only one type of final compounds.…”

Section: Green Chemistry and Non‐classical Activation Methodsmentioning

confidence: 99%

“…Dihydro‐1,2,4‐triazolo[1,5‐ a ]pyrimidines 253 a – h were synthesized in our research team to evaluate their antibacterial and antifungal activities [157] . Of the seven substances tested, only two compounds showed low activity against Gram‐positive S. aureus ( 253a , 253g MIC=25 μg/mL, MBC=50 μg/mL) and Gram‐negative P. aeruginosa ( 253a MIC=50 μg/mL, MBC=100 μg/mL).…”

Section: Partially Hydrogenated Azolopyrimidines In Drug Designmentioning

confidence: 99%

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Desenko,

Gorobets,

Lipson

et al. 2023

The Chemical Record

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Dihydroazolopyrimidines are an important class of heterocycles that are isosteric to natural purines and are therefore of great interest primarily as drug‐like molecules. In contrast to the heteroaromatic analogs, synthetic approaches to these compounds were developed much later, and their chemical properties and biological activity have not been studied in detail until recently. In the review, different ways to build dihydroazolopyrimidine systems from different building blocks are described – via the initial formation of a partially hydrogenated pyrimidine ring or an azole ring, as well as a one‐pot assembly of azole and azine fragments. Special attention is given to modern approaches: multicomponent reactions, green chemistry, and the use of non‐classical activation methods. Information on the chemical properties of dihydroazolopyrimidines and the prospects for their use in the design of drugs of various profiles are also summarized in this review.

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“…The test tubes with S. aureus, E. coli, P. aeruginosa crops were incubated at 37 ± 1 °C for 16-24 hours, with C. albicans crops -at 28 ± 1 °C for 44-48 hours. Minimum inhibitory concentration (MIC) was determined by visual absence of bacterial growth in the test tube with minimal concentration of investigated compound [10][11][12].…”

Section: Methodsmentioning

confidence: 99%

Clinical and social aspects of dysmenorrhea development

Dolhikh

Романенко

Иванченко

et al. 2019

Current Issues in Pharmacy and Medicine: Science and Practice

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Modern antibiotics and synthetic antimicrobial agents play a leading role in the treatment of bacterial infections. Despite their effectiveness, they cause a number of side effects, and thus the search for new antimicrobial and antifungal agents is currently one of the problems of pharmaceutical science of current interest. Literary data suggest that xanthine derivatives exhibit activity in relation to some strains of pathogenic microorganisms and fungi. The aim of this work is to develop a method for the synthesis of new derivatives of xanthine-8-aminoalkanoic acids and to study their physical and chemical properties, as well as their antimicrobial and antifungal effects. Materials and methods. The melting point has been determined with the help of an open capillary method with PTP-M device. Elemental analysis has been performed with the help of the instrument Elementar Vario L cube, NMR-spectra have been taken on a spectrometer Bruker SF-400 (operating frequency of 400 MHz, solvent DMSO, internal standard-TMS). Study of antimicrobial and antifungal activity of synthesized compounds has been performed by a twofold serial dilution method. Standard test strains have been used for the study:

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Multicomponent hot-water synthesis of 7-unsubstituted 4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines and their antimicrobial and antifungal activity

Cited by 15 publications

References 18 publications

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Clinical and social aspects of dysmenorrhea development

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