Cycloalkanecarbaldehydes in synthesis of novel 1,2-benzoxathiin-4(3H)-on 2,2-dioxide derivatives and study of the antimicrobial activity of synthesized compounds
| Autor: | Leonid A. Shemchuk, Dmytry Lega, Tetyana Osolodchenko, Galyna V. Grygoriv, Valentine P. Chernykh |
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| Rok vydání: | 2017 |
| Předmět: |
2-аміно-4Н-піран
багатокомпонентні реакції food.ingredient 2-діоксид циклоалканкарбальдегіди lcsh:RS1-441 2-бензоксатіїн-4(3Н)-он 2 антимікробна активність амонієві солі Antimicrobial Narrow spectrum lcsh:Pharmacy and materia medica chemistry.chemical_compound food chemistry Proton NMR Organic chemistry Agar Organic synthesis Ammonium General Pharmacology Toxicology and Pharmaceutics Methylene Malononitrile |
| Zdroj: | ScienceRise: Pharmaceutical Science, Vol 0, Iss 6 (10), Pp 4-10 (2017) |
| ISSN: | 2519-4852 2519-4844 |
| DOI: | 10.15587/2519-4852.2017.119279 |
| Popis: | Purpose: This paper is dedicated to the investigation of cycloalkanecarbaldehydes, 1,2-benzoxathiin-4(3H)-on 2,2-dioxide and active methylene nitriles interaction and to studying antimicrobial properties of the obtained compounds. Methods: As initial products were used cycloalkanecarbaldehydes 1,2-benzoxathiin-4(3H)-on 2,2-dioxide and active methylene nitriles. During the course of the research were applied the methods of organic synthesis. The structures of the obtained compounds were confirmed by elemental analysis and 1 H NMR spectroscopy. The antimicrobial activity was measured with the agar “well” diffusion method. Results: New 2-amino-4H-pyrans were synthesized by three-component reaction of cycloalkanecarbaldehydes, 1,2-benzoxathiin-4(3H)-on 2,2-dioxide and malononitrile. The replacement of the latter with ethylcyanoacetate in the case of cyclohexanecarbaldehyde led to the isolation of triethylammonium3-[(4-hydroxy-2,2-dioxido-2,1-benzoxathiin-3-yl)(cyclohexyl)methyl]-2,1-benzoxathiin-5-olat 2,2-dioxide. Based on this result and considering originality of such ammonium salts the latter were purposefully synthesized with two-component approach using a range of secondary and tertiary amines. The synthesized compounds demonstrated higher antimicrobial activity than the reference drugs against the gram-positive strains. Conclusions: The current research showed the prospective pathway for the expanding of the existing 2-amino-4H-pyrans diversity by utilizing in their synthesis such enolnucleophile and carbonyl compounds as 1,2-benzoxathiin-4(3H)-one 2,2-dioxide and cycloalkanecarbaldehydes respectively. The revealed antimicrobial activity of the obtained compounds against gram-positive microorganisms gives the opportunity for further investigations of narrow spectrum antibiotics among this group |
| Databáze: | OpenAIRE |
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