A series of benzotriazole, cyclic amides and pyrimidine derivatives, containing 2,6-di-tert-butyl-phenol fragments, were synthesized. The redox properties of obtained compounds were studied using the cyclic voltammetry on a platinum electrode in acetonitrile. The oxidation potentials of all substances were comparable to those of BHT. The obtained compounds were tested for their antibacterial activity, and N-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl)isatin (32 μg/mL) exerted good activity against Staphylococcus aureus.
In this work we suggest the new method for the synthesis of novel phenolic derivatives, containing lactamomethyl substituents. Oxidation processes of fuels and mineral oils lead to losing of their properties, so the search for new and effective inhibitors of these processes is very actuel. We suggest a facile system for lactamomethylation reaction. Heating in the water some of phenols (resorcinol, phloroglucinol, methylphloroglucinol, pyrogallol, salicylic, resorcilic and gallic acids) with N-hydroxymethyl derivatives of pyrrolidone, valerolactam, caprolactam and 4-phenylpyrrolidone in the presence of catalytic amounts of acetic acid led to the target compounds with nearly quantitative yields. Time of the reaction ranged 1.5-2 h. As the products have low solubility in water, in contrast with the reagents, filtration was used for their extraction. The advantages of this method are also that it is eco-friendly because of small amounts of wastes and low toxicity of the reagents and solvent, and cheapness of starting compounds. Eighteen novel compounds were obtained. The composition of target substances was determined by elemental analysis whereas the structures of the synthesized compounds were confirmed by FT-IR spectroscopy methods, 1H- and 13C-NMR spectroscopy. In IR spectra there are carbonyl group stretching vibrations peaks in lower frequencies (about 1600 cm-1) than expected due to the formation of inter- and intramolecular hydrogen bonds between this group and phenolic hydroxyl group.
Compounds with hindered phenolic moiety are known to be effective inhibitors of oxidative processes in different materials, moreover a number of phenols found to show wide spectrum of biological activity. At the same time, five-membered heterocycles exhibit unique properties, including antioxidant activity. One of the ways to create new effective antioxidants with a set of useful properties is to combine hindered phenol and a heterocyclic fragment in one molecule. In this work new 1-acyl-4-R-thiosemicarbazides were obtained during the reaction between 3-(4hydroxy-3,5-di-tert-butylphenyl)propanoic acid hydrazide and a number of isothiocyanates. 2-Amino-5-R-1,3,4-oxadiazoles were prepared in good yelds by heterocyclization of 1-acyl-4-Rthiosemicarbazides in presence of iodoxybenzoic acid and triethylamine. The antioxidant activity of 1,3,4-oxadiazoles was studied in vitro and was found to be higher than that of 4-methyl-2,6-ditert-butylphenol.
In recent decades, the chemistry of functionally substituted 1,2,4-triazoles and the fused heterocyclic systems based on them have received significant attention due to their structural and biological characteristics. The 1,2,4-triazole ring is a fragment of many fungicides such as fluconazole, intraconazole, and voriconazole. 1 3-R-4-Amino-1,2,4-triazole-5-thiones were found to exhibit antimicrobial and anti-inflammatory activity. 2-5 Fused heterocyclic triazoles also possess important clinical applications; thus, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles were reported as antiviral, antifungal, and antitumor agents. 6-8 Anti-HIV activity was also found. 9 Sterically hindered phenols were reported to possess anti-inflammatory and antimicrobial properties, 10,11 in addition to their well-known antioxidant activity. 12 As a continuation of our studies on the synthesis of azoles containing a hindered phenol moiety, 13,14 in the present work we have synthesized a number of novel compounds: substituted arylideneamino-2,4-dihydro-3H-1,2,4-triazole-3-thiones, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 6-aryl/alkyl-amino[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazoles, based on 3-(4-hydroxy-2,6-di-tert-butylphenyl) propanoic acid hydrazide, in search of new structures potentially exhibiting useful properties. In this study two different approaches were used to prepare the starting 4-amino-3-[2-(4-hydroxy-3,5-di-tert-butylphenyl)ethyl]-1,2,4-triazole-5-thione 3 (Scheme 1). In the first case, 15,16 the reaction of the hydrazide 1 with carbon disulfide and methyl iodide took place in ethanol to give the methyl ester of dithiocarbazic acid 2 in two stages over 24 hours (see Experimental section). Heterocyclization of the compound 2 with hydrazine hydrate lead to the formation of 3-R-4-amino-1,2,4-triazol-5-thione 3 in 55% yield. In the second case the 1,2,4-triazole 3 was obtained by the interaction of equimolar amounts of 3-(4-hydroxy-3,5-di-tert-butylphenyl)propanoic acid 4 and thiocarbohydrazide. According to the published data, 17,18 this approach involves, in most cases, a short-term fusion of the initial reagents, but, in our case, even short heating of the reaction mixture above the melting point led to the destruction of the starting acid. So the reaction was carried out by refluxing
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.