1,2,4-Triazolin-5-thione derivatives with anticancer activity as CK1γ kinase inhibitors

Pitucha, Monika; Janeczko, Monika; Klimek, Katarzyna; Fornal, Emilia; Woś, Maciej; Pachuta‐Stec, Anna; Ginalska, Grażyna; Kaczor, Agnieszka A.

doi:10.1016/j.bioorg.2020.103806

Cited by 16 publications

(8 citation statements)

References 45 publications

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“…According to the 1 H-NMR spectra; N-H protons of 1,4-disubstituted thiosemicarbazide derivatives (1a-9a), secondary amine NH protons of 2,5-disubstituted-1,3,4-thiadiazole derivatives (1b-9b) and NH protons of 2,4-dihydro-1,2,4-triazole-3-thiones (1c-9c) were determined in the range of 10.82-10.22, 9.70-9.31 and 8.30-7.85 ppm, 9.73.-7.20 ppm and 14.61-13.91 ppm in accordance with the literature [15], respectively. The triazole NH peaks for the compounds (1c-9c) were observed in the range of 14.61-13.91 ppm; confirming the thione formation [16]. These results showed that compounds with the thione form were the predominant tautomer in both solid and solution form of the molecules.…”

Section: Chemistrysupporting

confidence: 57%

Synthesis, structure elucidation and cytotoxic activities of 2,5-disubstituted-1,3,4-thiadiazole and l,2,4-triazole-3-thione derivatives

KANDEMİR,

KARAKUŞ,

ÖZBAŞ

et al. 2022

jrp

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In this study, a series of 1,3,4-thiadiazole (1b-9b) and l,2,4-triazole-3-thione (1c-9c) derivatives were synthesized. The reaction proses was carried out with the cyclocondensation of suitable 1,4-disubstituted thiosemicarbazide derivatives (1a-9a). The structures of the synthesized compounds were confirmed by the data obtained from elemental analysis, HPLC, UV, IR, 1 H-NMR and MS spectra. All of the compounds were tested for their cytotoxic activities against L929 fibroblast cells by MTT method. It was determined that the tested compounds 1a-9a, 1b-9b and 1c-9c were not cytotoxic at the studied concentrations (5.0 µg/mL and 10.0 µg/mL) in L929 cell lines. Compounds 1a-c, 2a-c, 3a-c, 4a-c, 5a-c and 8a-c showed increased growth inhibition whereas compounds 6a-c, 7a-c and 9a-c showed decreased growth inhibition on L929 cell lines

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Section: Chemistrysupporting

confidence: 57%

Synthesis, structure elucidation and cytotoxic activities of 2,5-disubstituted-1,3,4-thiadiazole and l,2,4-triazole-3-thione derivatives

KANDEMİR,

KARAKUŞ,

ÖZBAŞ

et al. 2022

jrp

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“…NCI-H460 is an non-small cell lung cancer cell line 18 ; A549 is a adenocarcinoma human alveolar basal epithelial cell line. 19 A previous study has showed that lung adenocarcinoma is a subtype of non-small cell lung cancer. 20 Moreover, NCI-H460 and A549 cell lines have been widely used for the detection of lung adenocarcinoma.…”

Section: Discussionmentioning

confidence: 99%

Down-Regulation of AHNAK2 Inhibits Cell Proliferation, Migration and Invasion Through Inactivating the MAPK Pathway in Lung Adenocarcinoma

Wang

Zheng²,

Cha

et al. 2020

Technol Cancer Res Treat

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AHNAK nucleoprotein 2 (AHNAK2) has been emerged as a crucial protein for neuroblast differentiation and cell migration, thereby involving in the development of various cancers. However, the specific molecular mechanism of AHNAK2 in lung adenocarcinoma is inconclusive. By accessing to the Oncomine dataset and GEPIA website, a higher expression level of AHNAK2 was observed in lung adenocarcinoma tissue samples. Overall survival (OS) curve plotted by Kaplan-Meier method showed that up-regulation of AHNAK2 was related with poor prognosis of lung adenocarcinoma patients. Quantitative reverse transcription polymerase chain reaction (qRT-PCR) analysis and western blot were conducted to examine the expression level of genes in lung adenocarcinoma cells. Through functional in vitro experiments, cell proliferation, migration and invasion were all suppressed after AHNAK2 knockdown using Cell counting kit-8 (CCK-8) assay, wound-healing and transwell analysis. Reduction of AHNAK2 decreased the apoptosis rate using flow cytometry analysis. Moreover, the key markers of MAPK pathway, p-MEK, p-ERK and p-P90RSK were decreased due to the transfection of si-AHNAK2 in A549 cells. U0126, a MEK inhibitor, showed the similar effects on MAPK-related protein levels with si-AHNAK2. To sum up, AHNAK2 is significantly increased in lung adenocarcinoma and plays a carcinogenic role by activating the MAPK signaling pathway, providing a novel insight and raising possibility for lung adenocarcinoma treatment.

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“…Furthermore, 1,2,4-triazole is a pharmacologically active scaffold that is crucial for therapeutic candidates such as anastrozole, vorozole, and letrozole, all of which have been shown to be efficient aromatase inhibitors and have applications in the treatment of breast cancer ( Ammazzalorso et al, 2021 ). Additionally, it was shown that 1,2,4-triazole containing mercapto scaffolds have antitubercular, antibacterial, antifungal, and anticancer effects ( Mallikarjuna et al, 2009 ; Pitucha et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

New quinoline-based triazole hybrid analogs as effective inhibitors of α-amylase and α-glucosidase: Preparation, in vitro evaluation, and molecular docking along with in silico studies

et al. 2022

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The 7-quinolinyl-bearing triazole analogs were synthesized (1d-19d) and further assessed in vitro for their inhibitory profile against α-amylase andαglucosidase. The entire analogs showed a diverse range of activities having IC 50 values between 0.80 ± 0.05 µM to 40.20 ± 0.70 µM (α-amylase) and 1.20 ± 0.10 µM to 43.30 ± 0.80 µM (α-glucosidase) under the positive control of acarbose (IC 50 = 10.30 ± 0.20 µM) (IC 50 = 9.80 ± 0.20 µM) as the standard drug. Among the synthesized scaffolds, seven scaffolds 12d, 10d, 8d, 9d, 11d, 5d, and 14d showed excellent α-amylase and α-glucosidase inhibitory potentials with IC 50 values of 4.

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1,2,4-Triazolin-5-thione derivatives with anticancer activity as CK1γ kinase inhibitors

Cited by 16 publications

References 45 publications

Synthesis, structure elucidation and cytotoxic activities of 2,5-disubstituted-1,3,4-thiadiazole and l,2,4-triazole-3-thione derivatives

Synthesis, structure elucidation and cytotoxic activities of 2,5-disubstituted-1,3,4-thiadiazole and l,2,4-triazole-3-thione derivatives

Down-Regulation of AHNAK2 Inhibits Cell Proliferation, Migration and Invasion Through Inactivating the MAPK Pathway in Lung Adenocarcinoma

New quinoline-based triazole hybrid analogs as effective inhibitors of α-amylase and α-glucosidase: Preparation, in vitro evaluation, and molecular docking along with in silico studies

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