Synthesis and properties of azoles and their derivatives. 36. Synthesis of 2-amino-1,3,4-oxadiazoles, 2-amino-1,3,4-thiadiazoles, and 1,2,4-triazoline-3-thiones containing indolyl radicals

Келарев, В. И.; Shvekhgeimer, G. A.; Lunin, A. F.

doi:10.1007/bf00506406

Cited by 6 publications

(2 citation statements)

References 4 publications

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“…In an attempt to obtain α-aceto-bromo-glucose, D-glucose was first treated with acetic anhydride in pyridin at room temperature, resulting in the produciton of 1,2,3,4,6-penta-O-acetylβ-glucose, then anomeric bromination of this compound with hydrogen bromide in acetic acid resulted in 2,3,4,6-tetra-O-acetylα-gluco-pyranosyl-bromide production. The presence of thiol-thione tautomerism is known for the compounds 3(a-c), and generally one form is predominant [25][26][27] . Thioglycosides of S-triazoles (7a-f) were synthesized by the reaction of 3-alkyl-4- amino-S-triazole-5-thione Schiff bases (5a-f) with the peracetylated β-pyranosyl-bromide [6] in the presence of potassium carbonate as a weak base in dry acetone (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

In Vitro Evaluation of Antimicrobial Properties of Some Newly Synthesized S-Triazole Thioglycosides

Firoozi

Dilmaghani

Ghezelbash

et al. 2021

IEM

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Backgrounds: Nowadays, the need for replacement of new drug structures is felt more than ever due to the spread of microbial resistance. S-triazoles are significant five-membered heterocyclic scaffolds due to their wide range of biological activities. Materials & Methods:A new series of Schiff bases (5a-f) were synthesized by the reaction of 4-amino-S-triazoles (3a-c) with furan and benzaldehyde 4(d-e). Then a novel series of triazole thioglycosides (7a-f) were synthesized by the reaction of Schiff bases (5a-f) and T-O-acetyle-α-D-glucopyranosyle-Br in the presence of potassium carbonate as a weak base in acetone. The structure of the products was confirmed by FT-IR, H-NMR, and C-NMR assays. The antimicrobial properties of the newly synthesized compounds were studied against four bacterial strains, including Bacillus cereus, Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli, and two fungal strains, including Aspergillus niger and Candida albicans. Findings: The synthesized compounds exhibited better antifungal activity than antibacterial activity, espetially 7d. Among all the compounds, the compound 7d was found to have the highest activity against C. albicans with IZ=18±0.7 mm, MIC=250 mg/mL, and MFC= 250 mg/mL. Conclusion:The present study results indicated that compounds containing S-triazole had the potential to be used in a wide variety of new antifungal formulations.

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Section: Resultsmentioning

confidence: 99%

In Vitro Evaluation of Antimicrobial Properties of Some Newly Synthesized S-Triazole Thioglycosides

Firoozi

Dilmaghani

Ghezelbash

et al. 2021

IEM

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“…В качестве синтонов были использованы N-ацил-тиосемикарбазиды различного строения, которые легко образуются из гидразида фенозан-кислоты. Из литературных данных известно, что N-ацил-тиосемикарбазиды в присутствии оснований цик-лизуются в 4-R-1,2,4-триазолин-5-тионы [15,16]. Этот метод был использован нами для синтеза 1,2,4-триазолин-5-тионов, содержащих фенольный заме-ститель в положении 3.…”

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Synthesis of Novel 4-R-1,2,4-Triazolin-5-Thiones Containing Space-Hindered Fragment of Phenol

Кошелев¹,

Ivanova²,

Alasadi³

et al. 2017

IVUZKKT

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Using of additives inhibiting free radical processes is necessary at production of the lubricating oils. In given article such kind target compounds were obtained from the number of new 1-acyl-4-R-thiosemicarbazides which were synthesized on the base of 3- (4-hydroxy-3,5-di-tert-butyl) propanoic acid hydrazide. The starting hydrazide was prepared from commercially available methyl ester (methylox) by refluxing in ethanol with a slight excess of hydrazine hydrate for 8 h. The best yields of the 1-acyl-4-R-isothiocyanates were achieved by refluxing equimolar amounts of isothiocyanates and hydrazide in isopropanol for 4-5 h. Under these conditions the yield was 75-85%. At further cyclization of intermediates obtained at a first step in aqueous sodium hydroxide for 1.5 h the corresponding 3-acyl-4-R-1,2,4-triazolin-5-thiones were obtained with the yield of 70-90%. Also, this method has absolute advantages due to a simple isolation of target compounds. Based on the IR-spectroscopy data in middle region and 1H NMR spectroscopy it was established that the substances obtained in the crystalline state and in DMSO solution exist in a form of thiones. The composition of obtained substances was determined with elemental analysis whereas the structures of the synthesized compounds were confirmed with FT-IR spectroscopy methods, 1H NMR spectroscopy and mass spectrometry.Forcitation:Koshelev V.N., Ivanova L.V., Alasadi R.T.Kh., Primerova O.V. Synthesis of novel 4-R-1,2,4-triazolin-5-thiones containing space-hindered fragment of phenol. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 3. P. 43-47.

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New 2,4-dihydro-1H-1,2,4-triazole-3-selones and 3,3′-di(4H-1,2,4-triazolyl)diselenides. Synthesis, biological evaluation, and in silico studies as antibacterial and fungicidal agents

oglu Askerov,

eL Bakri,

Osmanov

et al. 2023

Bioorganic Chemistry

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Synthesis and properties of azoles and their derivatives. 36. Synthesis of 2-amino-1,3,4-oxadiazoles, 2-amino-1,3,4-thiadiazoles, and 1,2,4-triazoline-3-thiones containing indolyl radicals

Cited by 6 publications

References 4 publications

In Vitro Evaluation of Antimicrobial Properties of Some Newly Synthesized S-Triazole Thioglycosides

In Vitro Evaluation of Antimicrobial Properties of Some Newly Synthesized S-Triazole Thioglycosides

Synthesis of Novel 4-R-1,2,4-Triazolin-5-Thiones Containing Space-Hindered Fragment of Phenol

New 2,4-dihydro-1H-1,2,4-triazole-3-selones and 3,3′-di(4H-1,2,4-triazolyl)diselenides. Synthesis, biological evaluation, and in silico studies as antibacterial and fungicidal agents

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