Design, synthesis and biological evaluation of novel 3-alkylsulfanyl-4-amino-1,2,4-triazole derivatives

Zhao, Pei‐Liang; Chen, Peng; Li, Qiu; Hu, Meng-Jin; Diao, Peng-Cheng; Pan, En-Shan; Wang, You

doi:10.1016/j.bmcl.2016.05.086

Cited by 25 publications

(4 citation statements)

References 24 publications

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“…Further, a series of novel 3-alkylsulfanyl-4-amino-1,2,4-triazoles 135 ( Fig. 30 ) was designed and evaluated for antitumor activity [ 126 ]. Compound 135d was found to have the highest potency with IC 50 values of 0.37, 2.94 and 31.31 μM against HCT116, HeLa and PC-3, respectively.…”

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

199

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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

199

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“…For N-substituted-3-mercapto-1,2,4-triazoles 3a,b and 7a-d, the IC50 values are 0.053, 0.089, 2.022, 1.299, 1.230, and 2.782 µM for HEPG2 respectively, while the IC50 values of MCF for the same compounds are 2.102, 1.092, 3.231, 1.672, 2.170, 1.592 µM respectively. Pei-LiangZhao et al, [50], synthesized as series of 3-alkylsulfanyl-4-amino-1,2,4-triazole (8p-2x) and showed IC50 over 100 on HEPG-2 & HCT-116 µM..…”

Section: Anticancer Activitymentioning

confidence: 99%

Synthesis and characterization of new 1,2,4-triazole anticancer scaffold derivatives: In Vitro study

et al. 2021

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Four Schiff bases were obtained via one direct click reaction between 3-amino-1H-1,2,4-triazole and different substituted benzaldehyde. The synthesized compounds were characterized on the basis of their spectral data including IR spectra, mass spectroscopy and 1 HNMR. The synthesized compounds were tested against three human cancer cell lines to evaluate their in vitro anticancer activity, and also tested on Vero cells extracted from African green monkey kidney to investigate their side effect. The screening showed that the Schiff bases TB-NO2 and TB-OCH3 produced an effective anticancer activity against HEPG2, HCT-116, and MCF-7 cell lines. Further investigations had been conducted to determine the apoptotic and antifibrotic ability of TB-NO2 and TB-OCH3 on MCF-7 cells by determining the expression of Bax, Bcl-2, CTGF, and PDGF. Results of Bax/Bcl-2 ratio for TB-NO2 and TB-OCH3 confirmed the apoptotic effect of these compounds on MCF-7 cells. The reduction in CTGF and PDGF genes expression confirmed the regulatory effect of these compounds on MCF-7 cells growth.

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“…Based on the reported method, the intermediates of 4-amino-5-aryl-2,4-dihydro-3H-1,2,4-triazole-3thiones (A) were prepared via four steps that includes esterification (1), hydrazide reaction (2), salt formation (3), and cyclization (4) (Scheme 2) [19][20][21][22]. The rude intermediates were purified using absolute ethanol, and the physicochemical properties and the results of EA analysis were summarized in Table S1.…”

Section: Scheme 1 Synthesis Of the Intermediatesmentioning

confidence: 99%

Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking

Li¹,

Ren²,

Han³

et al. 2021

Rev. Chim.

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Seven 4-amino-5-substituted-1,2,4-triazole-3-thione Schiff base compounds were synthesized reacting 4-amino-5-substituted-1,2,4-triazole-3-thione with dichloro-substituted 5-pyrimidines, and the structures were verified by elemental analysis and spectroscopic techniques (FT-IR, 1H NMR). Additionally, in vitro antifungal activities of the compounds (named F1~F2; A1~A5) against Grape anthracnose and Wheat gibberellic have been evaluated. The compounds of F1, A4 and A5 were found to be potentially effective antifungal agents against Grape anthracnose, while the others showed the low bioactivity. The antifungal activity of all compounds against Wheat gibberellic were superior to that of fluconazole (standard drug, SD). Particularly, compounds of F1, A1, A4 and A5 exhibited a broad-spectrum antifungal activity against two fungus as compared to the others. Therefore, molecular docking study was carried out to explore the potential interaction between ligands and Fusarium graminearum (PDB ID: 5E9H). The results showed that four compounds had higher affinity compared with fluconazole and form the stable complex with the receptor. Besides, the frontier molecular orbitals (FMOs) and molecular electrostatic potentials (MEP) of four compounds with broad-spectrum antimicrobial activity were also calculated with DFT/ B3LYP /6-31G (d, p) method. The energy gap values (△ELUMO-HOMO) of all the synthesized compounds ranged from 3.307-3.375 eV, which was lower than that of SD (6.248 eV). Additionally, according to MEP the electrophile reaction of 5-substituted groups was beneficial to improving the biological activity against Wheat gibberellic and Grape anthracnose.

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Design, synthesis and biological evaluation of novel 3-alkylsulfanyl-4-amino-1,2,4-triazole derivatives

Cited by 25 publications

References 24 publications

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

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

Synthesis and characterization of new 1,2,4-triazole anticancer scaffold derivatives: In Vitro study

Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking

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