Synthesis, characterization and antibacterial activity of some triazole Mannich bases carrying diphenylsulfone moieties

Almajan, Gabriela Laura; Bărbuceanu, Ștefania‐Felicia; Almajan, Eva-Ruxandra; Drăghici, Constantin; Şaramet, Gabriel

doi:10.1016/j.ejmech.2008.07.003

Cited by 82 publications

(60 citation statements)

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“…Finally, the compounds (19a-30a) were synthesized using the so-called Mannich reaction. Its mechanism has been extensively described by Almajan and co-workers [19]. The structures of the obtained compounds were confirmed on the basis of spectroscopic data and the results of elemental analyses.…”

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confidence: 50%

Studies on the Anticonvulsant Activity and Influence on GABA-ergic Neurotransmission of 1,2,4-Triazole-3-thione- Based Compounds

et al. 2014

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Abstract:The anticonvulsant activity of several 1,2,4-triazole-3-thione derivatives on mouse maximal electroshock-induced seizures was tested in this study. Characteristic features of all active compounds were rapid onset of action and long lasting effect. Structure-activity observations showed that the probability of obtaining compounds exerting anticonvulsant activity was much higher when at least one of the phenyl rings attached to 1,2,4-triazole nucleus had a substituent at the para position. The obtained results, moreover, permit us to conclude that despite the structural similarity of loreclezole (second-generation anticonvulsant drug) and the titled compounds, their anticonvulsant activity is achieved via completely different molecular mechanisms.

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confidence: 50%

Studies on the Anticonvulsant Activity and Influence on GABA-ergic Neurotransmission of 1,2,4-Triazole-3-thione- Based Compounds

et al. 2014

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“…Moreover, adamantane derivatives were also reported to exhibit marked anti-HIV [8][9][10], antibacterial [11][12][13], antimalarial [14], hypoglycemic [15,16], anti-inflammatory [17,18], and anticancer [19] activities. 1,2,4-Triazole derivatives were reported to possess significant anti-inflammatory [20,21] and antibacterial [22] activities. The title compound was prepared as an adamantanetriazole hybrid derivative as potential bioactive agent [23].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C₁₈H₂₀FN₃S

Al‐Shehri

Elsaman

Al‐Abdullah

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 18 H 20 FN 3 S, triclinic, P1, a = 7.3884(4) Å, b = 10.0741(6) Å, c = 12.6533(8) Å, α = 69.209(2)°, β = 73.778(2)°, γ = 72.638(2)°, The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. CCDC no.: 1507728 Source of material4-Fluorophenyl isothiocyanate (1.53 g, 0.01 mol) was added to a solution of adamantane-1-carbohydrazide (1.94 g, 0.01 mol), in ethanol (10 mL), and the mixture was heated under reflux with stirring for one hour. The solvent was then distilled off in vacuo; an aqueous sodium hydroxide solution (10%, 15 mL) was added to the residue and the mixture was heated under reflux for two hours then filtered hot. On cooling, the mixture was acidified with hydrochloric acid (pH 1-2) and the precipitated crude product was filtered, washed with water, dried and crystallized from aqueous ethanol to yield 3.03 g (92%) of the title compound (C 18 H 20 FN 3 S) as

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“…Dapsone [13] and Promine [14] (Figure 2) are specimens of some famous drugs, that comprise diaryl sulfone function, and are widely available in the market. Notably, the blend of a diaryl sulfone ring with several forms of heterocyclic equivalents exhibited significant biological actions [15][16][17][18][19]. Therefore, the insertion of a diaryl sulfone moiety to the DHPMs could provide novel derivatives of expected biological and pharmacological activities.…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free Biginelli Reactions Catalyzed by Hierarchical Zeolite Utilizing a Ball Mill Technique: A Green Sustainable Process

et al. 2017

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Abstract:A sustainable, green one-pot process for the synthesis of dihydropyrimidinones (DHPMs) derivatives by a three-component reaction of β-ketoester derivatives, aldehyde and urea or thiourea over the alkali-treated H-ZSM-5 zeolite under ball-milling was developed. Isolation of the product with ethyl acetate shadowed by vanishing of solvent was applied. The hierachical zeolite catalyst (MFI27_6) showed high yield (86%-96%) of DHPMs in a very short time (10-30 min). The recyclability of the catalyst for the subsequent reactions was examined in four subsequent runs. The catalyst was shown to be robust without a detectable reduction in catalytic activity, and high yields of products showed the efficient protocol of the Biginelli reactions.

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Synthesis, characterization and antibacterial activity of some triazole Mannich bases carrying diphenylsulfone moieties

Cited by 82 publications

References 14 publications

Studies on the Anticonvulsant Activity and Influence on GABA-ergic Neurotransmission of 1,2,4-Triazole-3-thione- Based Compounds

Studies on the Anticonvulsant Activity and Influence on GABA-ergic Neurotransmission of 1,2,4-Triazole-3-thione- Based Compounds

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C₁₈H₂₀FN₃S

Solvent-Free Biginelli Reactions Catalyzed by Hierarchical Zeolite Utilizing a Ball Mill Technique: A Green Sustainable Process

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Synthesis, characterization and antibacterial activity of some triazole Mannich bases carrying diphenylsulfone moieties

Cited by 82 publications

References 14 publications

Studies on the Anticonvulsant Activity and Influence on GABA-ergic Neurotransmission of 1,2,4-Triazole-3-thione- Based Compounds

Studies on the Anticonvulsant Activity and Influence on GABA-ergic Neurotransmission of 1,2,4-Triazole-3-thione- Based Compounds

Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S

Solvent-Free Biginelli Reactions Catalyzed by Hierarchical Zeolite Utilizing a Ball Mill Technique: A Green Sustainable Process

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Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C₁₈H₂₀FN₃S