Discovery of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity

Jilloju, Parameshwara Chary; Persoons, Leentje; Kurapati, Sathish Kumar; Schols, Dominique; Jonghe, Steven De; Daelemans, Dirk; Vedula, Rajeswar Rao

doi:10.1007/s11030-021-10258-8

Cited by 14 publications

(7 citation statements)

References 50 publications

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“…Recently, pyrazole and dihydrothiadiazine skeletons were obtained by a one-pot four-component reaction [ 110 ]. Initially, a mixture of acetylacetone 118 , 4-amino-5-hydrazinyl-4 H -1,2,4-triazole-3-thiol 119 , and diverse aldehydes 1 catalyzed by one drop of concentrated HCl in refluxing ethanol for 5–7 h afforded pyrazole-based intermediates 120 ( Scheme 13 ).…”

Section: Multicomponent Synthesis Of Biologically Active Pyrazole Der...mentioning

confidence: 99%

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

2022

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Pyrazole and its derivatives are considered a privileged N-heterocycle with immense therapeutic potential. Over the last few decades, the pot, atom, and step economy (PASE) synthesis of pyrazole derivatives by multicomponent reactions (MCRs) has gained increasing popularity in pharmaceutical and medicinal chemistry. The present review summarizes the recent developments of multicomponent reactions for the synthesis of biologically active molecules containing the pyrazole moiety. Particularly, it covers the articles published from 2015 to date related to antibacterial, anticancer, antifungal, antioxidant, α-glucosidase and α-amylase inhibitory, anti-inflammatory, antimycobacterial, antimalarial, and miscellaneous activities of pyrazole derivatives obtained exclusively via an MCR. The reported analytical and activity data, plausible synthetic mechanisms, and molecular docking simulations are organized in concise tables, schemes, and figures to facilitate comparison and underscore the key points of this review. We hope that this review will be helpful in the quest for developing more biologically active molecules and marketed drugs containing the pyrazole moiety.

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Section: Multicomponent Synthesis Of Biologically Active Pyrazole Der...mentioning

confidence: 99%

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

2022

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“…It has been considered a supernatural moiety or magic moiety [37][38][39][40][41]. Thiadiazine-based substances exhibit antiproliferative activity against a number of in vitro cancer cell lines, including lung carcinoma (A549), hepatocellular carcinoma (Hep3B), breast cancer (MCF-7), and prostate (PC-3), by targeting and interfering with DNA and stimulating cell cycle arrest, which causes cancer cells to undergo apoptosis [42][43][44]. Another class of heterocyclic compounds containing pyridine and thiazole moieties was designed, synthesized, and characterized by various spectral approaches.…”

Section: Introductionmentioning

confidence: 99%

Anticancer Studies of Newly Synthesized Thiazole Derivatives: Synthesis, Characterization, Biological Activity, and Molecular Docking

Al-Salmi,

Alrohaimi,

Behery

et al. 2023

Crystals

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Thiazole and its derivatives have received a lot of attention from researchers due to its wide biological, pharmacological, and anticancer properties. A novel series of 2-[2-[4-Hydroxy-3-substituted benzylidene hydrazinyl]-thiazole-4[5H]-ones (4a–c) and acetoxy derivative (5) were synthesized via using thiosemicarbazones (2a–c). The structure of the thiazole derivatives (4a–c) and 5 in these compounds was confirmed by spectroscopic techniques (IR and NMR), as well as elemental investigations. The synthesized derivatives biological activity was assessed based on their capacity to suppress the growth of the cancer cell lines MCF-7 and HepG2, as well as to halt the cell cycle and trigger apoptosis. Among the synthesized thiazole derivatives, compound 4c was found the most active derivative, with inhibitory concentrations IC50 = 2.57 ± 0.16 and 7.26 ± 0.44 µM in MCF-7 and HepG2, respectively, compared to Staurosporine as the standard drug with IC50 6.77 ± 0.41 and 8.4 ± 0.51 µM, respectively. Additionally, compound 4c blocked vesicular endothelial growth factor receptor-2 (VEGFR-2), according to our results (IC50 = 0.15 µM), compared to Sorafenib (IC50 = 0.059 µM) as the standard drug. Moreover, compound 4c induced cell cycle arrest at the G1/S phase, increasing the percentage and accumulation of cancer cells (DNA content) in the pre-G1 phase by 37.36% in MCF-7 cancer cells compared to untreated MCF-7 cells at 2.02%. Also, compound 4c increased the percentage of early and late apoptosis from 0.51% and 0.29%, respectively, in the case of the MCF-7 untreated control sample to 22.39% and 9.51%, respectively, in the MCF-7 treated sample. Furthermore, molecular docking studies of compounds 4a–c and 5 were conducted with four key proteins (aromatase, epidermal growth factor receptor (EGFR), cyclin-dependent kinase 2 (CDK2), and B-cell lymphoma 2 (Bcl-2)) that stimulate the growth, proliferation, and development of cancer cells. Compound 4c exhibited good docking scores with a promising and potential binding affinity toward the active site of selected docked proteins. According to these results, compound 4c showed efficient cytotoxic activity against the tested cancer cells.

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“…It was shown that small changes in the structure of the phenyl group could change the biological qualities to make them more effective against viruses or tumors. These compounds have the ability to fight tumors due to stopping tubulin from polymerizing [ 63 ].…”

Section: Synthesis Of Triazolo[34- B ]Thiadiazinesmentioning

confidence: 99%

Synthetic Methods and Pharmacological Potentials of Triazolothiadiazines: A Review

Mostafa,

Radini,

El-Rahman

et al. 2024

Molecules

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This review article examines the synthetic pathways for triazolothiadiazine derivatives, such as triazolo[3,4-b]thiadiazines, triazolo[5,1-b]thiadiazines, and triazolo[4,3-c]thiadiazines, originating from triazole derivatives, thiadiazine derivatives, or thiocarbohydrazide. The triazolothiadiazine derivatives exhibit several biological actions, including antibacterial, anticancer, antiviral, antiproliferative, analgesic, anti-inflammatory, and antioxidant properties. The review article aims to assist researchers in creating new biologically active compounds for designing target-oriented triazolothiadiazine-based medicines to treat multifunctional disorders.

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Discovery of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity

Cited by 14 publications

References 50 publications

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

Anticancer Studies of Newly Synthesized Thiazole Derivatives: Synthesis, Characterization, Biological Activity, and Molecular Docking

Synthetic Methods and Pharmacological Potentials of Triazolothiadiazines: A Review

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