A new compound tetramethyl 1,1′-(2-[{4,5-bis(methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate) (3) was prepared in two steps starting from 2-((4-methylphenyl)sulfonamido)-2-((tosyloxy)methyl)propane-1,3-diylbis(4-methylbenzenesulfonate) (1), with an overall yield of 74%. The key step being the copper-free Huisgen cycloaddition between N-(1,3-diazido-2-(azidomethyl)propan-2-yl)-4-methylbenzenesulfonamide (2) and commercially available dimethyl acetylenedicarboxylate. The chemical structure of compound 3 was determined by IR, 1D and 2D NMR experiments, and elemental analysis.
In this article, we describe the synthesis of two new triheterocyclic regioisomers, named 4-({4-[(1H-1,2,4-triazol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}methyl)-4-ethyl-2-phenyl-4,5-dihydrooxazole and 4-({5-[(1H-1,2,4-triazol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}methyl)-4-ethyl-2-phenyl-4,5-dihydrooxazole. The action of 1-(propargyl)-1H-1,2,4-triazole on 4-(azidomethyl)-4-ethyl-2-phenyl-4,5-dihydrooxazole, in a very small quantity of toluene, led after 48 hours at 120 °C to two regioisomers with an overall yield of 90%. The allocation of structures to these two regioisomers was carried out based on a comparative spectroscopic study using 1D NMR of the proton and carbon 13, as well as based on data from the literature concerning the cycloaddition reaction.
We have previously published new biheterocyclic phospohonic -amino esters of the 1,2,3-triazole-benzimidazole and 1,2,3-triazole-carbazole type. The aim of the present paper was to describe a new phosponic aminoester bearing a triazole ring substituted in position 5 by an ester group. Thus, according to the same catalytic process used previously, the compound naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate was synthesized with an excellent yield and high regioselectivity via the copper (I)-catalyzed alkyne–azide cycloaddition reaction (CuAAC), using diethyl (-azido(benzamido)methyl)phosphonate (1) as a dipole and 2- naphthyl propiolate as a dipolarophile (2). The structure of the new compound was fully characterized by 1D (31P, 1H, 13C) and 2D (1H-1H and 1H-13C) NMR spectroscopy, IR, and HRMS.
Bacterial resistance to antibiotics and disinfectants has become a real concern. The hospital presents a favorable environment for the colonization and development of bacteria resistant to antibiotics and disinfectants. The search for new antimicrobial compounds is essential to combat this phenomenon. Tetrazole derivatives may represent a solution due to their interesting antibacterial activity. In this work, two tetrazole derivatives; thiophene-2-carbaldehyde (T2C) and 5-(thiophen-2-yl)-1H-tetrazole (5TPh-1HT), were evaluated for their antibacterial activities against a set of reference strains and strains isolated from the hospital environment. The antibacterial effect was studied by the disc diffusion method and by determination of MIC and MBC. The 5-(thiophen-2-yl)-1H-tetrazole (5TPh-1HT) has a broader spectrum of activity than its oxime derivative (T2C). The latter has bactericidal activity only on gram-negative Escherichia coli, Pseudomonas aeruginosa with MICs ranging from 0.62 mg/ml to 2.5 mg/ml, while 5TPh-1HT has a bactericidal effect on all strains with MICs ranging from 0.62 mg/ml to 1.25 mg/ml. Both products have a significant inhibitory activity on the strains tested in particular E. coli H, S. aureus H, P. aeruginosa and Streptococcus spp A. It was found that these activities vary depending on the microbial strain tested and the product applied.
The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was established on the basis of NMR spectroscopy (1H, 13C), MS data and elemental analysis.
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