Design, synthesis, biological evaluation, and molecular docking study on triazine based derivatives as anti-inflammatory agents

Asadi, Parvin; Alvani, Mohsen; Hajhashemi, Valiollah; Rostami, Mahboubeh; Khodarahmi, Ghadamali

doi:10.1016/j.molstruc.2021.130760

Cited by 16 publications

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“…Based on this study's results, compound 5d at all the tested doses (50, 100, and 200 mg/kg) and compounds 10a and 10e at a dose of 200 mg/ kg significantly inhibited the early phase, and this means that these compounds might have additional mechanisms of action. Also, the molecular docking performed in the previous study predicted that the best compounds for inhibition of COX-2 were 5c and 10c while, surprisingly, the pharmacological study showed that compounds 5c and 5d among the vanillin derivatives and 10a, 10b, and 10e among the phenylpyrazole-triazine derivatives had the best anti-inflammatory activity [21], and the present study also emphasized the potent antinociceptive effect of these compounds. Therefore, it might be concluded that mechanisms other than inhibition of COX-2 might also be involved, but further studies are needed for determining a definite mechanism.…”

Section: Discussionsupporting

confidence: 59%

“…Five compounds derived from triazine that showed considerable anti-inflammatory activity in the previous study were synthesized and provided by Asadi et al [ 21 ] for evaluation of their possible antinociceptive effects. They include:…”

Section: Methodsmentioning

confidence: 99%

“…Considering the structural properties of COX-2 inhibitors, Asadi et al [ 21 ] synthesized new compounds with a heterocyclic ring based on triazine and evaluated their anti-inflammatory effect. In the continuation of this research, the present study aimed to evaluate the antinociceptive effects of selected triazine derivatives in mice.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of the antinociceptive effects of a selection of triazine derivatives in mice

et al. 2022

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Background: The authors showed in a previous study that some novel triazine derivatives had an anti-inflammatory effect. The present study was designed to evaluate the antinociceptive effect of five out of nine compounds including two vanillintriazine (5c and 5d) and three phenylpyrazole-triazine (10a, 10b, 10e) derivatives which showed the best anti-inflammatory effect. Methods: Male Swiss mice (25-30 g) were used. To assess the antinociceptive effect, acetic acid-writhing, formalin, and hot plate tests were used after intraperitoneal injection of each compound. Results: All compounds significantly (P < 0.001) reduced acetic acid-induced writhing at tested doses (50, 100, and 200 mg/kg). Also, the percent inhibition of writhing in the acetic acid test showed that at the maximum tested dose of these compounds (200 mg/kg), the order of potencies is as follows: 10b > 10a > 10e > 5d > 5c. In the formalin test, compounds 5d, 10a, and 10e showed an antinociceptive effect in the acute phase and all compounds were effective in the chronic phase. In the hot plate test, compounds 5c, 5d, and 10a demonstrated an antinociceptive effect. Conclusions: The results clearly showed that both vanillin-triazine and phenylpyrazole-triazine derivatives had an antinociceptive effect. Also, some compounds which showed activity in the early phase of formalin test as well as in the hot plate test could control acute pain in addition to chronic or inflammatory pain.

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Section: Discussionsupporting

confidence: 59%

Section: Methodsmentioning

confidence: 99%

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Evaluation of the antinociceptive effects of a selection of triazine derivatives in mice

et al. 2022

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“…The literature has reported other biological activities of s -triazine derivatives, including antimicrobial, antimalarial, anti-inflammatory, , antibacterial and antifungal, antioxidant, anticholinesterase, , and antiviral activity . In this regard, s -triazine can be considered a promiscuous molecule.…”

Section: Introductionmentioning

confidence: 99%

“…10 Many other compounds carrying an s-triazine scaffold, including compounds IV 11 and V 12 for EGFR-TK inhibitors, compound VI ZSTK474 (PI3K/MEK dual inhibitors), 1 3 compound VII, named Bimiralisib (PQR309), 14−16 and compound VIII as a dual inhibitor of PI3K/mTOR, have been reported as anticancer agents targeting EGFR/PI3K/AKT/mTOR cascades (Figure 1). 17 The literature has reported other biological activities of striazine derivatives, 18 including antimicrobial, 19 antimalarial, 20 anti-inflammatory, 21,22 antibacterial and antifungal, 11 antioxidant, anticholinesterase, 23,24 and antiviral activity. 25 In this regard, s-triazine can be considered a promiscuous molecule.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Activity of a New Series of Mono- and Bis(dimethylpyrazolyl)-s-triazine Derivatives Targeting EGFR/PI3K/AKT/mTOR Signaling Cascades

et al. 2022

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Here, we synthesized a newseries of mono - and bis (dimethylpyrazolyl)- s -triazine derivatives. The synthetic methodology involved the reaction of different mono- and dihydrazinyl- s -triazine derivatives with acetylacetone in the presence of triethylamine to produce the corresponding target products in high yield and purity. The antiproliferative activity of the novel mono - and bis (dimethylpyrazolyl)- s -triazine derivatives was studied against three cancer cell lines, namely, MCF-7, HCT-116, and HepG2. N -(4-Bromophenyl)-4-(3,5-dimethyl-1 H -pyrazol-1-yl)-6-morpholino-1,3,5-triazin-2-amine 4f , N -(4-chlorophenyl)-4,6-bis(3,5-dimethyl-1 H -pyrazol-1-yl)-1,3,5-triazin-2-amine 5c , and 4,6- bis (3,5-dimethyl-1 H -pyrazol-1-yl)- N -(4-methoxyphenyl)-1,3,5-triazin-2-amine 5d showed promising activity against these cancer cells: 4f [(IC 50 = 4.53 ± 0.30 μM (MCF-7); 0.50 ± 0.080 μM (HCT-116); and 3.01 ± 0.49 μM (HepG2)]; 5d [(IC 50 = 3.66 ± 0.96 μM (HCT-116); and 5.42 ± 0.82 μM (HepG2)]; and 5c [(IC 50 = 2.29 ± 0.92 μM (MCF-7)]. Molecular docking studies revealed good binding affinity with the receptor targeting EGFR/PI3K/AKT/mTOR signaling cascades. Compound 4f exhibited potent EGFR inhibitory activity with an IC 50 value of 61 nM compared to that of Tamoxifen (IC 50 value of 69 nM), with EGFR inhibition of 83 and 84%, respectively, at a concentration of 10 μM. Interestingly, 4f showed remarkable PI3K/AKT/mTOR inhibitory activity with 0.18-, 0.27-, and 0.39-fold decrease in their concentration (reduction in controls from 6.64, 45.39, and 86.39 ng/mL to 1.24, 12.35, and 34.36 ng/mL, respectively). Hence, the synthetic 1,3,5-triazine derivative 4f exhibited promising antiproliferative activity in HCT-116 cells through apoptosis induction by targeting the EGFR and its downstream pathway.

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Synthesis and Anti‐Fungal/Oomycete Activity of Novel Sulfonamide Derivatives Containing Camphor Scaffold

Yang

Sun

Jin

et al. 2022

Chemistry & Biodiversity

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Twelve novel camphor sulfonamide derivatives 2a -2l were synthesized and characterized by 1 H-NMR, 13 C-NMR and HRMS spectra. The anti-fungal/oomycete activity bioassay showed that some of the title compounds displayed moderate to good anti-fungal/oomycete activities against B. dothidea and P. capsici. Compound 2d exhibited the best in vitro antifungal activity toward B. dothidea. The in vivo experiment revealed that compound 2d possessed considerable anti-B. dothidea effect at 200 mg/L. Mechanism study showed that compound 2d could increase the cell membrane permeability. In addition, the in vitro enzyme inhibition assay and molecular docking results indicated that compound 2d could be a potential SDH inhibitor.

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Design, synthesis, biological evaluation, and molecular docking study on triazine based derivatives as anti-inflammatory agents

Cited by 16 publications

References 30 publications

Evaluation of the antinociceptive effects of a selection of triazine derivatives in mice

Evaluation of the antinociceptive effects of a selection of triazine derivatives in mice

Synthesis and Antiproliferative Activity of a New Series of Mono- and Bis(dimethylpyrazolyl)-s-triazine Derivatives Targeting EGFR/PI3K/AKT/mTOR Signaling Cascades

Synthesis and Anti‐Fungal/Oomycete Activity of Novel Sulfonamide Derivatives Containing Camphor Scaffold

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