Discovery of [1,2,4]triazolo[1,5-a]pyrimidines derivatives as potential anticancer agents

Huo, Jin-Ling; Wang, Shuai; Yuan, Xianglin; Zhao, Wen; Liu, Hong‐Min

doi:10.1016/j.ejmech.2020.113108

Cited by 15 publications

(8 citation statements)

References 26 publications

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“…In contrast, spectra with a resolved hyperfine structure, typical of weak exchange, were obtained for field orientations in the range of 20 to 160 • . The g tensor for both complexes was an axial one with g = 2.24 and g ⊥ = 2.06 for complex (1) and g = 2.25 and g ⊥ = 2.057 for complex (2). The hyperfine coupling constants A = 16.7 mT for complex (1) and A = 14 mT for complex (2), respectively, were obtained.…”

Section: Epr Spectroscopy Solid-state Epr Spectroscopymentioning

confidence: 88%

“…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%

“…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%

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

et al. 2021

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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.

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Section: Epr Spectroscopy Solid-state Epr Spectroscopymentioning

confidence: 88%

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

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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“…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

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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.

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Lewis Acid Catalyzed [3+3] Annulation/Aldol Condensation in Water: One Pot Synthesis of (E,E)‐4,6‐Bis(styryl)‐Pyrimidines

et al. 2022

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An efficient and facile one pot synthesis of (E,E)‐4,6‐bis(styryl)‐pyrimidines has been developed. It involves one pot two step reactions in environmentally benign solvent water, where first step involves pyrimidine ring formation from acetylacetone and urea via [3+3] annulation, followed by aldol condensation with differently substituted aromatic aldehyde to give desired (E,E)‐4,6‐bis(styryl)‐pyrimidines in moderate to good yields.

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Discovery of [1,2,4]triazolo[1,5-a]pyrimidines derivatives as potential anticancer agents

Cited by 15 publications

References 26 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

Lewis Acid Catalyzed [3+3] Annulation/Aldol Condensation in Water: One Pot Synthesis of (E,E)‐4,6‐Bis(styryl)‐Pyrimidines

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