Novel thiazolo[3,2-b]-1,2,4-triazoles derived from naproxen with analgesic/anti-inflammatory properties: Synthesis, biological evaluation and molecular modeling studies

Sarıgöl, Deniz; Uzgören-Baran, Ayşe; Tel, Banu Cahide; Somuncuoglu, Elif Inci; Kazkayası, İnci; Özadali-Sari, Keriman; Tan, Oya Ünsal; Okay, G.; Ertan, Mevlüt; Tozkoparan, Birsen

doi:10.1016/j.bmc.2015.03.049

Cited by 109 publications

(42 citation statements)

References 21 publications

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“…The authors concluded that the esterification of the free carboxylic acid of ibuprofen did not affect the anti-inflammatory and analgesic activity of the compound but suppressed gastric ulceration. Novel thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one naproxen derivatives were synthesized and evaluated for anti-inflammatory and analgesic effect in mice [28]. In the carrageenan-induced paw edema, used to determine anti-inflammatory effect, oral administration of the compounds at 50 mg/kg showed for some of the new compounds an effect comparable to that of naproxen.…”

Section: Resultsmentioning

confidence: 99%

Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs

et al. 2015

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Abstract:The aim of the study was to assess changes in the activity of anti-inflammatory terpenes from Chilean medicinal plants after the formation of derivatives incorporating synthetic anti-inflammatory agents. Ten new hybrid molecules were synthesized combining terpenes (ferruginol (1), imbricatolic acid (2) and oleanolic acid (3)) with ibuprofen (4) or naproxen (5). The topical anti-inflammatory activity of the compounds was assessed in mice by the arachidonic acid (AA) and 12-O-tetradecanoyl phorbol 13-acetate (TPA) induced ear edema assays. Basal cytotoxicity was determined towards human lung fibroblasts, gastric epithelial cells and hepatocytes. At 1.4 µmol/mouse, a strong anti-inflammatory effect in the TPA assay was observed for oleanoyl ibuprofenate 12 (79.9%) and oleanoyl ibuprofenate methyl ester 15 (80.0%). In the AA assay, the best activity was observed for 12 at 3.2 µmol/mouse, with 56.8% reduction of inflammation, in the same range as nimesulide (48.9%). All the OPEN ACCESSMolecules 2015, 20 11220 terpenyl-synthetic anti-inflammatory hybrids showed better effects in the TPA assay, with best activity for 6, 12 and 15. The cytotoxicity of the compounds 8 and 10 with a free COOH, was higher than that of 2. The derivatives from 3 were less toxic than the triterpene. Several of the new compounds presented better anti-inflammatory effect and lower cytotoxicity than the parent terpenes.

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Section: Resultsmentioning

confidence: 99%

Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs

et al. 2015

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“…Thus, literature data indicate that numerous thiazolo [3,2-b] [1,2,4] triazoles derivatives have been reported to possess antibacterial, [3][4][5][6][7][8][9] antifungal, 3,[6][7][8][9] anti-inflammatory, 3,10,11) analgesic, 3,10) antiproliferative, 12) anticonvulsant 13) properties. Also, thiazolo [3,2-b][1,2,4] triazol-ones have been studied for their properties with respect to their biological activities including anti-inflammatory, [14][15][16][17] analgesic, 15,17) anticancer, [18][19][20] antibacterial, 21) antifungal 21) and anticonvulsant. 22) Another interesting class are diarylsulfones which are important intermediates in organic synthesis because of their chemical properties and biological activities being known especially as antibacterial agents.…”

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confidence: 99%

Design, Synthesis, Characterization and Antimicrobial Evaluation of Some Heterocyclic Condensed Systems with Bridgehead Nitrogen from Thiazolotriazole Class

Bărbuceanu

Drăghici

Bărbuceanu

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Bioactivity analysis indicated that the compounds have good inhibitory effects on the tested bacteria . Several studies have shown that triazole derivatives have biological activities such as anti‐inflammatory, antibacterial, antifungal, antiviral, anticancer, and antituberculosis . For example, Singh et al developed a series of substituted aryl azide compounds containing o ‐phenylenediamines, which exhibited antifungal activities .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of chalcone derivatives containing thioether triazole

Chen

et al. 2020

Journal of Heterocyclic Chem

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The infection of Xanthomonas oryzae pv. Oryzae (Xoo), Ralstonia solanacearum (Rs), and Xanthomonas axonopodis pv. Citri (Xac) has become a major problem in agricultural production. In this study, a series of novel chalcone derivatives containing thioether triazoles were designed and synthesized. The structures of the novel compounds were systematically characterized via 1H‐NMR, 13C‐NMR, and HRMS. Moreover, the antibacterial activity results showed that E10, E11, E15, and E16 have adequate antibacterial activities against Xoo, Rs, and Xac. Among the different compounds, E15 exhibited remarkable inhibitory effect against Xac with an EC50 of 9.1 μg.mL‐1, which was better than that of commercial agent bismerthiazol (54.9 μg.mL‐1). In addition, the possible antibacterial mechanism of the target compound E15 against Xac was studied via scanning electron microscopy (SEM).

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Novel thiazolo[3,2-b]-1,2,4-triazoles derived from naproxen with analgesic/anti-inflammatory properties: Synthesis, biological evaluation and molecular modeling studies

Cited by 109 publications

References 21 publications

Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs

Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs

Design, Synthesis, Characterization and Antimicrobial Evaluation of Some Heterocyclic Condensed Systems with Bridgehead Nitrogen from Thiazolotriazole Class

Synthesis and antibacterial activity of chalcone derivatives containing thioether triazole

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