Авторы: Krupnova I.A., Sukhanov G.T.
Название публикации: Synthesis and Properties of Products of Nucleophilic Substitution of the Nitro Group in 1-Methyl-5-nitro-3R-1,2,4 Triazoles with O-Nucleophiles
Название источника: Chemistry for Sustainable Development
Библиографическая ссылка: Krupnova I.A., Sukhanov G.T. Synthesis and Properties of Products of Nucleophilic Substitution of the Nitro Group in 1-Methyl-5-nitro-3R-1,2,4 Triazoles with O-Nucleophiles // Chemistry for Sustainable Development. - 2017. - Iss.5. - P.?-?.
Ссылки: DOI: 10.15372/KhUR20170511; РИНЦ: 30510252;
Реферат: Modern medical science widely uses the following drugs that include 1,2,4-triazole structure: fluconazole, ribavirin, trazodone etc . In terms of fundamental research, the interest to 1,2,4-triazole derivatives is driven by great opportunities of structural design, which in turn opens up prospects to develop new generation functional materials with predetermined properties. Nucleophilic substitution may become one of the methods of functionalisation of 1,2,4-triazole ring at a carbon atom. 1-Methyl-5-nitro-3R-1,2,4-triazoles enter into a substitution reaction of the nitro group (SNipso) with mono- and diatomic alcohols (tyrosol, phenylethanol, resorcin, hydroquinone) producing conjugates in 63.0-83.0 % yields, as demonstrated. Interaction process monitoring of initial substrates with O-nucleophiles and analysis of the resulting reaction products are carried out using 1H NMR spectroscopy. The rate and direction of nucleophilic substitution reaction depend on both the structure of the initial substrate and the nature of the O-nucleophile, as established. The process is accompanied by competitive reactions of the substrate with hydroxide anion and triazolone formed in this reaction. Consequently, the same N-C triazolyltriazolone structure, i.e . 2,2'-dimethyl-2Н,2'Н-[3,4']bi([1,2,4]triazolyl)-3'-one is recorded in reaction products, regardless of the alcohol used. Products of nucleophilic substitution of the nitro group in 1-methyl-5-nitro-3R-1,2,4-triazoles by mono- and dibasic alcohols show activity (antiischemic, antihypertensive, and antiarrhythmic) that is currently of high interest in Russia and abroad for treatment and prevention of cardiovascular diseases, as demonstrated using PASS Online computer program. By using the method of holes, it is experimentally found that 1,3-dimethyl-5-(2-phenylethoxy)-1H-1,2,4-triazole displays antimicrobial activity against phytopathogenic fungi of the Fusarium oxysporum species.
Ключевые слова: 1-метил-5-нитро-3R-1,2,4-триазолы, конъюгаты, ароматические спирты, нуклеофильное замещение, бифункциональный О-нуклеофил, биологическая активность, 1-methyl-5-nitro-3R-1,2,4-triazoles, conjugates, aromatic alcohols, nucleophilic substitution, bifunctional O-nucleophile, biological activity
Год опуликования: 2017
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