Design, synthesis, anticonvulsant activity, and pharmacophore study of new 1,5-diaryl-1H-1,2,4-triazole-3-carboxamide derivatives

Abuelhassan, Abdelfattah H.; Badran, Mostafa; Hassan, Heba A.; Abdelhamed, Dalia; El‐Nabtity, Sameh M.; Aly, Omar M.

doi:10.1007/s00044-017-2114-4

Cited by 10 publications

(3 citation statements)

References 28 publications

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“…reported the anticonvulsant activity of 1,5-diaryl-1 H -1,2,4-triazole-3-carboxamide derivatives 167 ( Fig. 36 ) against MES, scPTZ and Strychnine animal screen methods [ 152 ]. Most of the compounds showed parallel activity pattern with standard phenytoin and valparate.…”

Section: Biological Activities Of 124-triazole Derivativesmentioning

confidence: 99%

An insight on medicinal attributes of 1,2,4-triazoles

Aggarwal

Sumran²

2020

European Journal of Medicinal Chemistry

173

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The present review aims to summarize the pharmacological profile of 1,2,4-triazole, one of the emerging privileged scaffold, as antifungal, antibacterial, anticancer, anticonvulsant, antituberculosis, antiviral, antiparasitic, analgesic and anti-inflammatory agents, etc. along with structure-activity relationship. The comprehensive compilation of work carried out in the last decade on 1,2,4-triazole nucleus will provide inevitable scope for researchers for the advancement of novel potential drug candidates having better efficacy and selectivity.

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Section: Biological Activities Of 124-triazole Derivativesmentioning

confidence: 99%

An insight on medicinal attributes of 1,2,4-triazoles

Aggarwal

Sumran²

2020

European Journal of Medicinal Chemistry

173

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“…Synthesis of triazoles and their biological importance have received considerable attention in recent years, and this class of compounds have become one of the potential agents for drug discovery. − Among these, 1,2,4-triazoles represent an important class of organic compounds with wide use in medicine, agriculture, and industry . A wide variety of therapeutically interesting drug candidates possessing analgesic, anti-inflammatory, anti-microbial, anti-cancer, anti-depressant, anti-fungal, anti-convulsant, and anti-viral activities are discussed in the literature possessing the 1,2,4-triazole moiety. − …”

Section: Introductionmentioning

confidence: 99%

(Benzylideneamino)triazole–Thione Derivatives of Flurbiprofen: An Efficient Microwave-Assisted Synthesis and In Vivo Analgesic Potential

et al. 2021

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Triazole is an imperative heterocycle renowned for its broad-spectrum biological significance. In this manuscript, facile microwave-assisted synthesis of a series of 4-(benzylideneamino)-3-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1H-1,2,4-triazole-5(4H)-thione 6(a–m) derivatives along with their in vivo analgesic activity is reported. 2-(2-Fluoro-[1,1′-biphenyl]-4-yl)propanoic acid (flurbiprofen) was converted to methyl 2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanoate using microwave irradiation, followed by its hydrazinolysis with hydrazine monohydrate. 2-(2-Fluoro-[1,1′-biphenyl]-4-yl)propanehydrazide thus obtained was converted to 4-amino-3-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1H-1,2,4-triazole-5(4H)-thione, followed by its condensation with different aromatic aldehydes to get the title compounds. Structures of all the synthesized compounds were established using different methods (1H NMR and 13C NMR spectroscopies, mass spectrometry, and elemental analysis) and evaluated for their potential as analgesic agents by tail flick, hot plate, and writhing methods. The results of this in vivo study revealed several compounds as potent analgesic agents among which compound 6e showed significant analgesic effect for all the three assays employed.

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“…Some of the modern drugs which containing a triazole moiety are alprazolam, triazolam, estazolam (hypnotic, sedative, tranquilizer), trazodone (antidepressant, anxiolytic), trapidil (hypotensive), terconazole (antifungal), hexaconazole (antifungal), etizolam (amnesic, anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant), rilmazafon (hypnotic, anxiolytic) and rizatriptan (antimigraine agent) (Sahu et al 2013). 1,2,4-Triazole and 4,5dihydro-1H-1,2,4-triazol-5-one derivatives have been found to have a broad spectrum of biological activities (Kaczor et al 2013;Aktaş-Yokuş et al 2015;Thakkar et al 2017;Yüksek et al 1997;Abuelhassan et al 2018;Khalid et al 2018).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation and molecular docking studies of new 2-ethoxy-4-{[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonate derivatives on human aldose reductase enzyme

Özdemir¹,

Kılınç²,

Manap³

et al. 2021

Preprint

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A series of 2-ethoxy-4-{[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonates (3) were synthesized from the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with 2-ethoxy-4-formyl-phenyl benzenesulfonate (2). N-acetyl derivatives (4) of compounds 3 were also obtained. Then, the compounds 3 have been treated with morpholine and 2,6-dimethylmorpholine in the presence of formaldehyde to synthesize 2-ethoxy-4-{[1-(morpholine-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonates (5) and 2-ethoxy-4-{[1-(2,6-dimethylmorpholine-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonates (6), respectively. The structures of twenty-six new compounds were identified by using elemental analysis, IR, 1H NMR, 13C NMR, and MS spectral data. In addition, in vitro antibacterial activities of the new compounds were evaluated against six bacteria such as Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Bacillus cereus and Klepsiella pneumonia according to agar well diffusion method. Furthermore, in order to determine the possible antidiabetic properties of the synthesized 1,2,4-triazole derivatives, inhibition effects on the AR enzyme were investigated and molecular docking studies were carried out to determine the receptor-ligand interactions of these compounds. IC50 values of triazole-derived compounds (6a, 6b, 6d-g) against AR enzyme were determined as 0.95 µM, 0.75 µM, 1.83 µM, 0.62 µM, 1.05 µM, 1.06 µM, respectively. Considering the docking scores and binding energies obtained docking studies, it has been shown that molecules fit very well to the active site of the AR enzyme.

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Design, synthesis, anticonvulsant activity, and pharmacophore study of new 1,5-diaryl-1H-1,2,4-triazole-3-carboxamide derivatives

Cited by 10 publications

References 28 publications

An insight on medicinal attributes of 1,2,4-triazoles

An insight on medicinal attributes of 1,2,4-triazoles

(Benzylideneamino)triazole–Thione Derivatives of Flurbiprofen: An Efficient Microwave-Assisted Synthesis and In Vivo Analgesic Potential

Synthesis, biological evaluation and molecular docking studies of new 2-ethoxy-4-{[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonate derivatives on human aldose reductase enzyme

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