Recent Development of 1,2,4-triazole-containing Compounds as Anticancer Agents

Xiao, Wen; Zhou, Yonggang; Zeng, Junhao

doi:10.2174/1568026620666200128143230

Cited by 39 publications

(22 citation statements)

References 130 publications

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“…It was found that the 1,2,4‐triazole moiety play a significant role in various pharmaceutical applications [1–6] including anti cancer activity [7–9] . In particular, several hybrid molecules were synthesized by the hybridisation of 1,2,4‐triazole ring with other heterocyclic rings as potent anticancer agents [10–18] .…”

Section: Introductionmentioning

confidence: 99%

“…It was found that the 1,2,4-triazole moiety play a significant role in various pharmaceutical applications [1][2][3][4][5][6] including anti cancer activity. [7][8][9] In particular, several hybrid molecules were synthesized by the hybridisation of 1,2,4-triazole ring with other heterocyclic rings as potent anticancer agents. [10][11][12][13][14][15][16][17][18] On the other aspect, the quinoxaline derivatives are recognized as a novel group of cancer chemotherapeutic targets with noteworthy therapeutic efficiency in opposition of solid tumors.…”

Section: Introductionmentioning

confidence: 99%

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In vitro Anticancer and Insilico Studies of Quinoxaline‐sulfonyl‐1,2,4‐triazole Hybrids

Dasari¹,

Banala²,

Nukala³

et al. 2022

ChemistrySelect

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New quinoxaline‐sulfonyl‐1,2,4‐triazole hybrids were synthesized (5 a–n) via systematic step‐wise sequence. Later, the in vitro cytotoxicity screening of all these compounds revealed that 2‐((4‐morpholino‐[1,2,4]triazolo[4,3‐a]quinoxalin‐1‐yl)sulfonyl)‐1‐(4‐nitrophenyl)ethenone (5 b), 1‐(4‐methoxy phenyl)‐2‐((4‐morpholino‐[1,2,4]triazolo[4,3‐a]quinoxalin‐1‐yl)sulfonyl) ethenone (5 d),4‐(2‐((4‐morpholino‐[1,2,4]triazolo[4,3‐a] quinoxaline‐1‐yl)sulfonyl)acetyl)benzonitrilen (5 g), 1‐(3,4‐dichloro phenyl)‐2‐((4‐morpholino[1,2,4]triazolo[4,3‐a]quinoxalin‐1‐yl) sulfonyl) ethenone (5 j) and 1‐(2,5‐dimethoxyphenyl)‐2‐((4‐morpholino[1,2,4]triazolo[4,3‐a]quinoxalin‐1‐yl)sulfonyl) ethenone (5 k) were found to more active against the four human cancer cell lines like Hep‐G2 (liver), A‐549 (lung), MCF‐7 (breast) and DU‐145 (prostate) with IC50 values ranging from 1.95±1.34 to 9.61 ±1.72 μM, whereas standard drug displayed IC50 values ranging from 1.97±0.45 to 3.08±0.13 μM. Predominately, compound 5 j displayed superior cytotoxicity against all cell lines than the standard etoposide. As well, the insilico studies of compounds 5 b, 5 d, 5 g, 5 j, and 5 k on EGFR receptor revealed that most potent compound 5 j strongly binds to protein EGFR (pdbid:4HJO). Finally, compounds 5 j and 5 g displayed superior inhibitory activity against tyrosine kinase EGFR than the standard erlotinib.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

In vitro Anticancer and Insilico Studies of Quinoxaline‐sulfonyl‐1,2,4‐triazole Hybrids

Dasari¹,

Banala²,

Nukala³

et al. 2022

ChemistrySelect

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“…Many drugs (such as triazolam, alprazolam, rufinamide, fluconazole, itraconazole, lamtidine, ribavirin, brassinazole, and sitagliptin) assembling the triazole moiety have already been used in clinics for the treatment of various diseases. Moreover, a terrific amount of triazole-contained derivatives have been designed and prepared to discover new anticonvulsants ( Song and Deng, 2018 ), anti-Alzheimer ( Xu et al, 2019 ), anticancer ( Wen et al, 2020 ), antibacterial ( Gao et al, 2019 ), antifungal ( Peyton et al, 2015 ), and anti-inflammatory agents ( Zhou and Wang, 2012 ).…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Anticonvulsant Activities of New Triazolopyrimidine Derivatives

et al. 2022

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Epilepsy, a severe brain disease affecting a large population, is treated mainly by antiepileptic drugs (AEDs). However, toxicity, intolerance, and low efficiency of the available AEDs have prompted the continual attempts in the discovery of new AEDs. In this study, we discovered a skeleton of triazolopyrimidine for the development of new AEDs. The design, synthesis, in vivo anticonvulsant activity evaluation of triazolopyrimidines (3a–3i and 6a–6e), and pyrazolopyrimidines (4a–4i) are reported. We found that most triazolopyrimidines showed anticonvulsive activity in the maximal electroshock (MES) and pentetrazol (PTZ)-induced seizure models. On the contrary, pyrazolopyrimidines (4a–4i) showed weak or no protective effects. Among the tested derivatives, compound 6d, holding a median effective dose (ED50) of 15.8 and 14.1 mg/kg against MES and PTZ-induced seizures, respectively, was found to be the most potent one. Moreover, the protection index (PI) value of 6d was significantly higher than that of the available AEDs such as valproate, carbamazepine, and diazepam. The antiepileptic efficacy of compound 6d was also observed in the 3-mercaptopropionic acid and bicuculline-induced seizure models. Antagonistic effects of flumazenil and 3-MP for the anticonvulsive activity of 6d and also the radioligand-binding assay confirmed the involvement of GABA receptors, at least benzodiazepine (BZD) receptor, in the anticonvulsant activity of compound 6d. The docking study of compounds 4e and 6d with GABAA receptor confirmed and explained their affinity to the BZD receptors.

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“…However, drug resistance, side effects, low selectivity, and severe toxicity are the major disadvantages of current drugs. Therefore, there is an urgent need to develop new anticancer drugs with great e ciency and high speci city [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Docking, ADME and Biological Evaluation Studies of Some New 1,3,4-oxadiazole Linked Benzimidazoles as Anticancer Agents and Aromatase Inhibitors

Çevik

Çeli̇k

Işık

et al. 2021

Preprint

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In this study, due to the potential anticancer effects of the benzimidazole ring system, a series of benzimidazole-1,3,4-oxadiazole derivatives were synthesized and characterized by 1H NMR, 13C NMR, and MS spectra analyses. In the in vitro anticancer assay, all the compounds tested anticancer activities using MTT-based assay against five cancer cell lines (MCF-7, A549, HeLa, C6, and HepG2). Among them, compound 5a exhibited the most potent activity with IC50 values of 5,165±0,211 μM and 5,995±0,264 μM against MCF-7 and HepG2 cell lines. Compound 5a was included in the BrdU test to determine the DNA synthesis inhibition effects for both cell types. Furthermore, compound 5c was also found to be more effective than doxorubicin on the HeLa cell line. The selectivity of anticancer activity was evaluated in NIH3T3 (mouse embryo fibroblast cell line) cell line. In vitro, enzymatic inhibition assays of aromatase enzyme were performed for compound 5a acting on the MCF-7 cell line. For compound 5a, in silico molecular docking against aromatase enzyme was performed to determine possible protein-ligand interactions and binding modes.

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Recent Development of 1,2,4-triazole-containing Compounds as Anticancer Agents

Cited by 39 publications

References 130 publications

In vitro Anticancer and Insilico Studies of Quinoxaline‐sulfonyl‐1,2,4‐triazole Hybrids

In vitro Anticancer and Insilico Studies of Quinoxaline‐sulfonyl‐1,2,4‐triazole Hybrids

Design, Synthesis, and Evaluation of Anticonvulsant Activities of New Triazolopyrimidine Derivatives

Design, Synthesis, Molecular Docking, ADME and Biological Evaluation Studies of Some New 1,3,4-oxadiazole Linked Benzimidazoles as Anticancer Agents and Aromatase Inhibitors

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