Synthesis of New Derivatives of 1,2,3‐Triazole‐Linked Phthalazine‐1,4‐dione in Water: Experimental Aspects and Molecular Docking Calculations

Abstract

A new series of phthalazine‐based 1,2,3‐triazole derivatives are synthesized by the reaction of 2‐methyl‐3‐(prop‐2‐yn‐1‐yl)‐2,3‐dihydro‐phthalazine‐1,4‐dione or 2,3‐bis(prop‐2‐yn‐1‐yl)‐2,3‐dihydrophthalaz‐ine‐1,4‐dione with aromatic azides via copper‐catalyzed azide‐alkyne cycloaddition reactions in the presence of metformine as a ligand. These reaction procedures have the advantages of high‐to‐excellent yields, short reaction times, mild experimental conditions, and operational simplicity. All the synthesized compounds are screened in vitro for their anti‐bacterial activities against the three bacterial strains Micrococcus luteus, Pseudomonas aeruginosa, and Bacillus subtilis. Furthermore, the results of anti‐bacterial activity of the synthesized compounds was investigated using molecular docking calculations.

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

“…The 13 C NMR data of these compounds were highly compatible with those in the literature. [37,38] In the second part of the synthesis study, the target compounds, thioether-bridged 2,6-disubstituted imidazo [2,1-b] [1,3,4]thiadiazole derivatives (7a-7i and 8a-8i), which contained both imidazole and thiadiazole rings, were obtained from the reactions of the starting compounds (4 and 5) with phenacyl bromide derivatives (6a-6i) in ethanol (at yields of 66% to 79%). The target compounds were synthesized using the synthetic pathway shown in Scheme 1.…”

“…These compounds are used as therapeutic agents in pharmaceutical chemistry and are found in the structures of many commercially available drugs. [2,3] The heterocyclic derivatives of imidazole (C 3 H 4 N 2 ), which is an important member of the heterocyclic aromatic compounds, have been widely studied in the field of pharmaceutical chemistry and other fields due to their versatile use and various biological activities. [4][5][6][7][8] Thiadiazole is a heterocyclic aromatic compound that has a five-member ring with 2 nitrogen atoms and one sulfur atom, in addition to carbon and hydrogen atoms.…”

“…[9] Among these isomers, 1,3,4-thiadiazole and its derivatives are especially highly reactive against many chemical reactions, and there have been many studies in the literature on the synthesis and characterization of these compounds due to their biological activities. [10][11][12][13] Heterocyclic systems in which these two bioactive compounds (imidazole and 1,3,4-thiadiazole) are fused to each other with a bridgehead nitrogen atom are referred to as imidazo [2,1-b] [1,3,4]thiadiazoles. [14][15][16] These fused heterocyclic compounds and their derivatives have become widely used compounds in pharmaceutical chemistry due to their wide variety of biological activities, such as antifungal, antibacterial, antimicrobial, antioxidant, anticonvulsant, antiviral, antidepressant, antiinflammatory, antihypertensive, antituberculosis, and antiproliferative activities.…”

“…[10,[17][18][19][20][21][22][23][24][25][26][27][28][29] Moreover, the synthesis of these compounds and their derivatives has also become a commonly investigated topic in anticancer activity studies due to their structures being similar those of Levamisole, Tetramisole, and Dexamisole, which are good immune system regulators and enhancers. [30,31] In light of the important literature data mentioned above, this study focused on the synthesis of thioetherbridged 2,6-disubstituted imidazo [2,1-b] [1,3,4]thiadiazole derivatives, their characterization by various spectroscopic methods, and an investigation of their antifungal activity against various plant pathogens. In addition, in silico absorption, distribution, metabolism, elimination (ADME) parameters were calculated to evaluate the drug-likeness of the synthesized compounds.…”

Synthesis of 1,2,3 triazole‐linked pyrimidines catalyzed by mg‐Al‐LDH‐immobilized‐CuI as a heterogeneous catalyst

“…In continuing our interest in the synthesis of 1,2,3‐triazole‐linked to heterocyclic compounds, we decided to synthesize new 1,2,3 triazole‐linked pyrimidines catalyzed by CuI/Mg‐Al‐LDH.…”