10.1007/s12039-011-0138-8
The research focuses on the efficient green synthesis of Schiff bases and azetidinones derivatised with 1,2,4-triazoles. The study employs Mg(ClO4)2 as a catalyst for the synthesis of Schiff bases from 1-amino-2-aryl-3-oxo-1,2,4-triazoles with various aldehydes under solvent-free conditions. The resulting Schiff bases are then reacted with chloroacetyl chloride to yield azetidinones, also in solvent-free conditions, with excellent yields. The synthesized compounds were analyzed for their potential as drugs by evaluating properties such as penetration into biological membranes (clogP), drug-likeliness, and drug scores. Additionally, the compounds were screened for antitubercular and antimicrobial activities. The analyses included techniques such as IR spectroscopy, 1H NMR spectroscopy, mass spectrometry, and elemental analysis, as well as thin layer chromatography (TLC) to check the purity of the compounds. The pharmacological evaluation was carried out at a separate facility, and the OSIRIS property explorer was used for computational drug analysis.
10.1016/j.jorganchem.2008.08.007
This study focuses on the synthesis and characterization of novel metallophthalocyanines bearing 1,2,4-triazole macromolecular substituents, which have important biological properties and potential applications in magnetochemical and optical sensing. This study involves the preparation of metallophthalocyanines [6–9; M = Ni(II), Zn(II), Co(II), and Cu(II)] using a series of chemical reactions starting from ethyl p-chlorobenzoylhydrazone (1) and passing through several intermediate compounds to finally obtain metallophthalocyanines 6–9. The synthesis was carried out under microwave irradiation and using reagents such as dimethylaminoethanol and anhydrous metal salts. The new compounds were characterized using a variety of analytical techniques including infrared (IR) spectroscopy, proton and carbon-13 nuclear magnetic resonance (1H NMR and 13C NMR), ultraviolet-visible (UV-Vis) spectroscopy and elemental analysis, as well as thermogravimetric analysis (TGA) to determine their thermal stability.
10.1080/15257770500544545
The research focuses on the microwave-assisted organic synthesis (MAOS) of 3-(D-gluco-pentitol-1-yl)-1H-1,2,4-triazole, a compound of interest in medicinal chemistry due to its pharmacological activities. The study aims to accelerate the synthesis of seco C-nucleosides of 1,2,4-triazole using microwave irradiation, which is reported to provide higher yields and purities compared to traditional synthetic methods. The chemicals used in the process include D-glucono- and D-galactono-1,5-lactones, thiocarbohydrazide, p-nitrobenzaldehyde, ethyl chloroacetate, and various reagents for subsequent reactions such as acetic anhydride, sodium acetate, and ammonium hydroxide. The conclusions of the research indicate that microwave irradiation significantly accelerates the synthesis of the target compounds, improving yields and reducing reaction times, thus demonstrating the effectiveness of MAOS in the synthesis of these potentially medicinally important compounds.
10.1007/s00044-013-0887-7
This research presents the synthesis and anticonvulsant evaluation of new 6-bromoimidazo[1,2-a]pyridine-2-carbohydrazide derivatives, which are designed to possess biologically active hydrazone functionality and substituted 1,2,4-triazole moieties. The purpose of the study was to develop novel antiepileptic drugs with improved therapeutic actions and reduced toxicity. The synthesis involved various chemicals such as 5-bromo-2-aminopyridine, ethyl bromopyruvate, hydrazine hydrate, aromatic aldehydes, carbon disulfide, potassium hydroxide, and different alkyl/benzyl halides. The structures of the synthesized compounds were confirmed through spectral techniques like FTIR, 1H NMR, 13C NMR, and mass spectrometry. The in vivo anticonvulsant properties were assessed using maximal electroshock seizure and subcutaneous pentylene tetrazole methods, with toxicity studies performed using the rotarod method. The research concluded that most of the new compounds exhibited significant anticonvulsant properties without toxicity up to 100 mg/kg, with compounds 3b and 4 showing complete protection against seizures, comparable to the standard drug diazepam. These findings suggest that linking imidazo[1,2-a]pyridines with triazole and hydrazone moieties can lead to potent anticonvulsants with minimal side effects.
10.1021/jo00253a029
The research investigates the formation of 1,3,5-trisubstituted 1,2,4-triazoles through cation radical-induced oxidative cycloaddition of arylhydrazones of benzaldehyde and butyraldehyde to various nitriles. The study aims to explore the mechanism and efficiency of this reaction pathway, comparing it with other known methods. Key chemicals used include thianthrenyl perchlorate (Th'+C104-) and tris(2,4-dibromophenyl)aminium hexachloroantimonate (Ar3N'+SbC16-) as cation radical oxidants, and aceto-, propio-, and acrylonitrile as nitrile substrates. The results show that the cation radical-induced reactions yield 1,2,4-triazoles with high efficiency, and the formation of 5-vinyltriazoles instead of 5-cyano-2-pyrazolines indicates that the reaction does not proceed through nitrilimines, as previously thought. This finding distinguishes the cation radical route from other documented cycloadditions and highlights its potential as a useful method for synthesizing 1,2,4-triazoles.
10.1139/v80-010
The study investigates the preparation, characterization, and reactions of N-tert-butyldimethylsilyl derivatives of various heterocyclic compounds, including imidazole, 2-methylimidazole, 4-methylimidazole, benzimidazole, pyrazole, 1,2,4-triazole, and benzotriazole. These derivatives were synthesized using tert-butyldimethylsilyl chloride and the corresponding heterocyclic compounds. The products were identified and characterized using carbon and proton nuclear magnetic resonance (NMR), mass spectrometry, and elemental analysis. The study confirmed the absence of intermolecular silyl exchange at ambient temperature through carbon NMR spectra, but noted that such exchange occurred at elevated temperatures (130-160°C). The study also explored the reaction of these silyl derivatives with dimethylsulfoxide (DMSO), resulting in the formation of N-(methylthio)methyl derivatives of the heterocycles. The mechanism for this reaction involves a Pummerer rearrangement, and the products were characterized using various analytical techniques, providing insights into the stability and reactivity of these compounds under different conditions.
10.1016/j.ejmech.2012.12.057
The research investigates the synthesis and biological evaluation of new pyrazole derivatives with potential antimicrobial and analgesic properties. The purpose of the study is to address the ongoing need for effective and affordable antimicrobial and analgesic agents by synthesizing and testing new compounds. The researchers synthesized three series of compounds (11a-d, 12a-d, and 13a-d) containing 1,2,4-triazoles and benzoxazoles with substituted pyrazole moieties. Key chemicals used in the synthesis include acid hydrazides, carbon disulfide, potassium hydroxide, hydrazine hydrate, and various substituted acetophenones. The newly synthesized compounds were characterized using IR, 1H NMR, mass spectrometry, and elemental analysis. The antimicrobial activity was assessed using the Minimum Inhibitory Concentration (MIC) method against bacterial strains such as Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa, as well as the fungal strain Candida albicans. The analgesic activity was evaluated using the tail flick method in rats. The results showed that compound 11c, featuring a 2,5-dichlorothiophene substituent on the pyrazole moiety and a triazole ring, exhibited significant antimicrobial and analgesic activity. The study concludes that the combination of pyrazole with 1,2,4-triazoles enhances pharmacological effects, making these compounds promising candidates for further development into more effective antimicrobial and analgesic drugs.
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