A Study on the Condensation Reaction of  4-Amino-3,5-dimethyl-1,2,4-triazole with Benzaldehydes: Structure and Spectroscopic Properties of Some New  Stable Hemiaminals

Wajda-Hermanowicz, Katarzyna; Pieniążczak, Damian; Zatajska, Aleksandra; Wróbel, Robert; Drabent, Krzysztof; Ciunik, Zbigniew

doi:10.3390/molecules200917109

Cited by 15 publications

(5 citation statements)

References 43 publications

(52 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Formation of hemiaminal ethers was also observed in the presence of molecular sieves [29]. Quite recently, the formation of stable hemiaminals was also described for the reactions of substituted 4-amine-1,2,4-triazoles [30][31][32] and 2-aminopyrimidine [33] with benzaldehydes.…”

Section: Introductionmentioning

confidence: 86%

Unassisted formation of hemiaminal ether from 4-aminopyridine and o-vanillin - experimental and theoretical study

2018

View full text Add to dashboard Cite

The reactions between o-vanillin and three isomeric aminopyridines lead to imines of diverse spatial conformation and reactivity. The direct products of these simple reactions carried out in methanol are either imine compounds formed in the reactions of 2-amino-and 3-aminopyridine with o-vanillin or the α-aminoether formed in the reaction of o-vanillin with 4-aminopyridine. The Schiff-type derivative of 4-aminopyridine and o-vanillin, which is described in this paper for the first time, is very reactive and can only be obtained indirectly from the α-aminoether in anhydrous conditions. All compounds are characterized by X-ray diffraction and FT-IR and NMR spectroscopies. The DFT calculations at all-electron BLYP/Q4ZP level of theory are utilized to explain the differences between the reactivity of isomeric aminopyridines and their imine derivatives.

show abstract

Section: Introductionmentioning

confidence: 86%

Unassisted formation of hemiaminal ether from 4-aminopyridine and o-vanillin - experimental and theoretical study

2018

View full text Add to dashboard Cite

show abstract

“…The 1,2,4-triazole motif is a part of a large number of chemotherapeutic drugs [19,20] which are useful as: anti-inflammatory [21,22], anti-depressant, antiviral, antifungal, antimicrobial [23][24][25][26][27], anticancer properties [28][29][30][31], antitubercular [32][33][34][35] and analgesic [36], activities. Owing to the huge possibility of exploration of biologically active molecules containing this moety, a lot of work has been done on the synthesis of 1,2,4-triazole Schiff base derivatives [37][38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%

A facile sonochemical protocol for synthesis of 3-amino- and 4-amino-1,2,4-triazole derived Schiff bases as potential antibacterial agents

et al. 2020

View full text Add to dashboard Cite

A facile method has been developed for the synthesis of Schiff bases derived from substituted and unsubstituted 3-amino-and 4-amino-1,2,4-triazoles. Condensation of the aminotrizoles with a variety of aromatic aldehydes afforded desired Schiff bases in excellent yields in 3-5 minutes of exposure to ultra-sound. The synthesized compounds were characterized by means of IR, 1 HNMR and Mass spectrometry. The synthesized compounds were also screened for their antibacterial potential against Gram-negative (Escherichia coli, Shigella sonnei, Pseudomonas aeruginosa and Salmonella typhi) and two Gram-positive (Staphylococcus aureus and Bacillus subtilis) strains.

show abstract

“…Напрями сучасної наукової роботи, що пов'язані з залученням названого синтону до структури нових перспективних сполук, є актуальними для багатьох наукових груп. Цьому сприяє багата історія в сфері створення тріазоловмісних лікарських засобів [3]. Так, у чинних протоколах лікування наведено численні протигрибкові лікарські засоби, анксіолітики, гепато-, нейро-та кардіопротектори, протиракові, протимігренозні та інші засоби; ще більше подібних сполук перебуває на різних стадіях клінічних досліджень.…”

Section: Resultsunclassified

“…Зауважимо, що сполуки 1, 2, 3, 4 і 5 мають необхідний ступінь насиченості молекул, що визначається часткою sp 3 -гібридних атомів Карбону на рівні 0,18. Для сполуки 6 цей показник становить 0,25, для 7 -0,31, що відповідає необхідному.…”

Section: результатиunclassified

Synthesis, molecular docking, and ADME analysis of a series of 4-amino-3,5-dimethyl-1,2,4-triazole derivatives

Kucherenko¹,

Brytanova²,

Gotsulya³

2023

АП

View full text Add to dashboard Cite

The heterocyclic system of 1,2,4-triazole enables the successful creation of promising biologically active compounds. By creating a range of derivatives based on 4-amino-3,5-dimethyl-1,2,4-triazole, the spectrum of potential biologically active compounds can be expanded. The aim of the work was the synthesis and in silico justification of the prospects for the search for biologically active compounds among 4-amino-3,5-dimethyl-1,2,4-triazole derivatives. Materials and methods. The work uses modern methods for synthesizing organic compounds, followed by confirmation of their individuality and structure through the analysis of physical-chemical parameters and spectroscopic techniques such as 1H NMR, IR spectroscopy, elemental analysis, and chromatography-mass spectrometry. To assess the similarity of the synthesized compounds to medicinal products, the SwissADME online tool was employed. The probability of impact on a number of enzyme systems (cyclooxygenase-2, lanosterol 14α-demethylase, anaplastic lymphoma kinase) was estimated using molecular docking. Results. A series of newly synthesized derivatives of 4-amino-3,5-dimethyl-1,2,4-triazole was obtained, and the synthesis conditions were optimized and their structures were confirmed. It was determined that there is a high probability of influencing lanosterol 14α-demethylase, highlighting the significance of further research on the antifungal activity of the synthesized compounds. Additionally, the potential influence on the activity of cyclooxygenase-2 and anaplastic lymphoma kinase was discovered. However, the probability of exhibiting the corresponding activities, namely anti-inflammatory and anti-cancer, is low. Physical indicators, parameters of pharmacokinetics, and drug-likeness are important, which determines the prospects of creating biologically active substances based on the synthesized series of compounds. Conclusions. A series of 4-((R-iden)amino)-3,5-dimethyl-1,2,4-triazoles were synthesized, and their general physical-chemical properties were determined. The overall potential for creating innovative biological products based on these compounds was assessed using in silico methods for predicting the activity of substances.

show abstract

A Study on the Condensation Reaction of 4-Amino-3,5-dimethyl-1,2,4-triazole with Benzaldehydes: Structure and Spectroscopic Properties of Some New Stable Hemiaminals

Cited by 15 publications

References 43 publications

Unassisted formation of hemiaminal ether from 4-aminopyridine and o-vanillin - experimental and theoretical study

Unassisted formation of hemiaminal ether from 4-aminopyridine and o-vanillin - experimental and theoretical study

A facile sonochemical protocol for synthesis of 3-amino- and 4-amino-1,2,4-triazole derived Schiff bases as potential antibacterial agents

Synthesis, molecular docking, and ADME analysis of a series of 4-amino-3,5-dimethyl-1,2,4-triazole derivatives

Contact Info

Product

Resources

About