Biological activities of [1,2,4]triazolo[1,5-a]pyrimidines and analogs

Pinheiro, Sérgio; Pinheiro, Erick M.C.; Muri, Estela M.F.; Pessôa, J. C.; Cadorini, Mayara A.; Greco, Sandro J.

doi:10.1007/s00044-020-02609-1

Cited by 33 publications

(44 citation statements)

References 184 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For B16 cells, when treated with (2), the cell viability decreased to 5%, with IC 50 values of 6.88 µg/mL (7.6 µM) after 24 h treatment and 4.15 µg/mL (4.58 µM) after 48 h, respectively (Table 3). The ligand dmtp did not affect the viability of either BJ or B16 cells at 24 or 48 h. It is worth mentioning that for other copper compounds tested on melanoma cells, the reported IC 50 values were similar [35][36][37][38][39][40][41][42][43], and only one study reported lower values [38] compared with those found for complex (1).…”

Section: Biological Characterization 231 Cell Viability and Lactate Dehydrogenase Assaysmentioning

confidence: 94%

“…The analysis of the packing diagram of both complexes reveals the formation of dimers between the cationic units and the free dmtp ligands. The dimers for compound (1) are shown in Figure 2, while those for compound (2) are presented in Supplementary Figures S1 and S2. Remarkably, both complexes crystallized with an additional uncoordinated dmtp ligand molecule in the asymmetric unit.…”

Section: Description Of the Crystal Structure Of Cu(ii) Complexesmentioning

confidence: 99%

“…The triazolopyrimidine derivatives are valuable pharmacophores based on their resemblance to purine bases. As result, several compounds bearing diverse substituents were developed as species with relevant biological activity [1]. The most recent findings in the field describe triazolopyrimidines as agents with potent antiproliferative activity by inducing G0/G1 phase arrest [2] or cellular apoptosis [3], as species with anti-HIV activity [4],…”

Section: Introductionmentioning

confidence: 99%

“…A promising activity, comparable with that of standard anticancer drugs, against a panel of cancer cell lines was reported for [1,2,4]triazolo [1,5-a]pyrimidine derivatives (tpds). Among these, some pyrimidine ring-disubstituted species exhibit a good activity against colon (HCT116) [9], human promyelocytic leukemia (HL60) [10], gastric (MGC-803), esophageal (EC 109), lung (A549 and PC-9) [11], liver (HepG2) [12] and breast (MCF-7) [12,13] cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Biological Activity of Triazolopyrimidine Copper(II) Complexes Modulated by an Auxiliary N-N-Chelating Heterocycle Ligands

et al. 2021

View full text Add to dashboard Cite

Novel complexes of type [Cu(N-N)(dmtp)2(OH2)](ClO4)2·dmtp ((1) N-N: 2,2′-bipyridine; (2) L: 1,10-phenantroline and dmtp: 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine) were designed in order to obtain biologically active compounds. Complexes were characterized as mononuclear species that crystallized in the space group P-1 of the triclinic system with a square pyramidal geometry around the copper (II). In addition to the antiproliferative effect on murine melanoma B16 cells, complex (1) exhibited low toxicity on normal BJ cells and did not affect membrane integrity. Complex (2) proved to be a more potent antimicrobial in comparison with (1), but both compounds were more active in comparison with dmtp—both against planktonic cells and biofilms. A stronger antimicrobial and antibiofilm effect was noticed against the Gram-positive strains, including methicillin-resistant Staphylococcus aureus (MRSA). Both electron paramagnetic resonance (EPR) and Saccharomyces cerevisiae studies indicated that the complexes were scavengers rather than reactive oxygen species promoters. Their DNA intercalating capacity was evidenced by modifications in both absorption and fluorescence spectra. Furthermore, both complexes exhibited nuclease-like activity, which increased in the presence of hydrogen peroxide.

show abstract

Section: Biological Characterization 231 Cell Viability and Lactate Dehydrogenase Assaysmentioning

confidence: 94%

Section: Description Of the Crystal Structure Of Cu(ii) Complexesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Biological Activity of Triazolopyrimidine Copper(II) Complexes Modulated by an Auxiliary N-N-Chelating Heterocycle Ligands

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Azolo[1,5-a]pyrimidines are a very diversified group of heterocycles [ 1 , 2 , 3 ]. Among them, many compounds find application due to their beneficial features, for example, photophysical properties [ 4 , 5 , 6 , 7 ], metal complexes [ 8 , 9 , 10 ], and as medicinal drugs for diabetes mellitus [ 11 , 12 , 13 ], viruses [ 14 , 15 , 16 ], bacteria [ 17 , 18 ], neurological diseases [ 19 , 20 ], tumor diseases [ 21 , 22 , 23 , 24 , 25 , 26 ], Alzheimer’s disease [ 27 , 28 , 29 ], etc.…”

Section: Introductionmentioning

confidence: 99%

Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation

et al. 2021

View full text Add to dashboard Cite

The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino-2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been refuted. Compounds with an electron-donor substituent at position seven undergo decomposition during oxidation. The phenomenon was explained based on experimental data, electro-chemical experiment, and quantum-chemical calculation. The mechanism of oxidative degradation has been proposed.

show abstract

Computational Studies for Development of Triazole‐Pyrimidines as Inhibitor of α‐Tubulin Receptor

Abdessadak,

Tabti,

Alaqarbeh

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

Microtubules are among the critical targets for chemotherapeutic agents to fight against cancer because of their crucial role in mitosis. Microtubule inhibitors block cell cycle progression and result in apoptosis, they can frequently disrupt microtubule/tubulin dynamics by binding to the α‐tubulin receptor. To this end, we have developed compounds against α‐tubulin receptor using several tools of computational chemistry: 3D‐QSAR, Molecular Docking, Molecular Dynamics Simulation, and ADMET prediction. The significant findings incorporated two reliable models: CoMFA (Q2=0.75; R2=0.89) and CoMSIA (Q2=0.57; R2=0.78). Molecular Docking was generated and validated using Molecular Dynamics simulation to investigate the binding mode between the most active compound and the α‐tubulin receptor. The results of the MD simulation demonstrated stability over a 100 ns period. Four compounds (C1, C2, C3, and C4) were developed based on the contour maps, and their activities were predicted. Additionally, Molecular Docking was executed to elucidate the interaction and affinity between the novel compounds and the α‐tubulin receptor. C1 exhibited high affinity and essential interactions and was subjected to MD simulation studies. The results of the MD simulation revealed that the modifications made to enhance the anticancer activity did not impact stability. Finally, ADMET analysis was utilized to examine drug‐likeness.

show abstract

Biological activities of [1,2,4]triazolo[1,5-a]pyrimidines and analogs

Cited by 33 publications

References 184 publications

Biological Activity of Triazolopyrimidine Copper(II) Complexes Modulated by an Auxiliary N-N-Chelating Heterocycle Ligands

Biological Activity of Triazolopyrimidine Copper(II) Complexes Modulated by an Auxiliary N-N-Chelating Heterocycle Ligands

Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation

Computational Studies for Development of Triazole‐Pyrimidines as Inhibitor of α‐Tubulin Receptor

Contact Info

Product

Resources

About