Synthesis of pyrazolo[3,4-d]pyrimidin-4(5H)-ones tethered to 1,2,3-triazoles and their evaluation as potential anticancer agents

Allam, Muralidhar; Bhavani, A. K. D.; Mudiraj, Anwita; Ranjan, Nikhil; Mallikarjuna, Thippana; Babu, Phanithi Prakash

doi:10.1016/j.ejmech.2018.06.055

Cited by 58 publications

(27 citation statements)

References 30 publications

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“…Hybrid compounds containing the pyrazolo[3,4-d]pyrimidinone and 1,2,3-triazole portions were evaluated against glioma cells such as human U87 and rat-C6. 74 Fig. 6) inhibited the proliferation of U87 cells by 47.69% and, owing to its good solubility in DMSO, was chosen for further evaluation.…”

Section: Diverse 123-triazole-containing Heterocyclic Hybridsmentioning

confidence: 99%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

614

289

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A B S T R A C TThe 1,2,3-triazole ring is a major pharmacophore system among nitrogen-containing heterocycles. These fivemembered heterocyclic motifs with three nitrogen heteroatoms can be prepared easily using 'click' chemistry with copper-or ruthenium-catalysed azide-alkyne cycloaddition reactions. Recently, the 'linker' property of 1,2,3-triazoles was demonstrated, and a novel class of 1,2,3-triazole-containing hybrids and conjugates was synthesised and evaluated as lead compounds for diverse biological targets. These lead compounds have been demonstrated as anticancer, antimicrobial, anti-tubercular, antiviral, antidiabetic, antimalarial, anti-leishmanial, and neuroprotective agents. The present review summarises advances in lead compounds of 1,2,3-triazolecontaining hybrids, conjugates, and their related heterocycles in medicinal chemistry published in 2018. This review will be useful to scientists in research fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology. Chemistry: synthesis and properties of the 1,2,3-triazolesThe general synthetic route of 1,2,3-triazoles using click chemistry is described in Scheme 1A. The most popular route to 1,2,3-triazoles is Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition, which is the https://doi.

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Section: Diverse 123-triazole-containing Heterocyclic Hybridsmentioning

confidence: 99%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

614

289

View full text Add to dashboard Cite

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“…The ligand binds in the hydrophobic pocket of the protein kinase domain and the binding mode is stabilized by the formation of hydrogen bonds between the ligand and active site residues of the protein. [52][53][54][55] Another compound 30 is a 1,2,3-triazole-based inhibitor, which is active against HGF-induced scattering of MDCK and GTL-16 cancer cells. The binding mode of the new compound is similar to that of the active compound triorcas; also, the range of IC 50 of the new compound is similar to that of triorcas.…”

Section: Introductionmentioning

confidence: 99%

CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review

et al. 2020

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“…Considering that 1 showed significant toxicity in glioma and breast cancer cells, we performed in silico studies with induced fit molecular docking approach. With reference to previous reports on triazole containing molecules, we selected 16 protein targets associated with different cancers of brain, breast and colon . The docking results are presented in Table , which includes docking scores, RMSD values of re‐docked and co‐crystallized ligands, MM‐GB/SA dG bind energies, and amino acid residues involved in hydrogen bonding with the acyclic nucleoside 1 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anti‐Proliferative Activity of a Triazole‐Fused Thymidine Analogue

et al. 2020

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Here we report the synthesis of two-an acyclic and a macrocyclic-analogues of thymidine linked to a triazole moiety. The new molecules were synthesized through an intramolecular 1,3-dipolar cycloaddition reaction of the diazido derivative of thymidine with a suitable alkyne. The acyclic nucleoside showed dose dependent cytotoxicity against glioblastoma and breast cancer cells by causing significant cellular damage as studied with confocal laser scanning microscopy. In silico induced fit molecular docking studies showed poly(ADP-ribose) polymerase 1 (PARP1) as a potential target of the acyclic nucleoside. On the other hand, both the analogues showed no toxicity against normal fibroblast cells. ChemistrySelectCommunications

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Synthesis of pyrazolo[3,4-d]pyrimidin-4(5H)-ones tethered to 1,2,3-triazoles and their evaluation as potential anticancer agents

Cited by 58 publications

References 30 publications

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review

Synthesis and Anti‐Proliferative Activity of a Triazole‐Fused Thymidine Analogue

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