Recent advances in 1,2,4-triazolo[1,5-a]pyrimidine chemistry

Fischer, G.

doi:10.1016/bs.aihch.2018.10.002

Cited by 29 publications

(15 citation statements)

References 381 publications

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“…A large number of publications devoted to the synthetic methods, chemical transformations, and application of azolopyrimidines indicate the high relevance of this group of compounds. − The diversity of the biological properties of azolopyrimidines is explained by their structural similarity to purine bases, which make them capable of interfering in key biochemical processes. Thus, azolopyrimidines have established themselves as antiviral, antibacterial, − antidiabetic, antitumor, , and antiglycation agents.…”

Section: Introductionmentioning

confidence: 99%

Benzimidazoazapurines: Design, Synthesis, and Photophysical Study

et al. 2021

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A highly efficient approach to a new class of polycyclic 8-azapurines, benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidines (BITPs), with good photophysical characteristics is proposed. The approach comprises condensation of aminobenzimidazoles with 3-oxo-2-phenylazopropionitrile to form 3-(arylazo)benzo[4,5]imidazo[1,2-a]pyrimidine-4-amines, which undergo oxidative cyclization by the catalytic action of copper(II) acetate, resulting in BITPs with 73–84% yield. Spectral investigations demonstrated the fluorescent properties of BITPs, exhibiting good quantum yields (up to 60%) with maxima absorption at 379–399 and emission at 471–505 nm.

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Section: Introductionmentioning

confidence: 99%

Benzimidazoazapurines: Design, Synthesis, and Photophysical Study

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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“…Pyroxsulam acts by inhibiting ALS, an important target for herbicides, which is an essential enzyme that catalyzes the rst step in the synthesis of the branched-chain amino acids valine, leucine and isoleucine [8]. The resulting lack of amino acids in the plant inhibits DNA synthesis, subsequently stopping cell division and causing death in susceptible plants [9]. Commercial formulations of pyroxsulam with the herbicide safener cloquintocet allow for selective weed control in cereal crops.…”

Section: Introductionmentioning

confidence: 99%

Integrated Transcriptomic and Metabolomic Analyses of the Molecular Mechanisms of Two Highland Barley Genotypes with Differential Pyroxsulam Responses

Weng¹,

Yan²,

Guo³

et al. 2021

Preprint

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Background: Highland barley is one of the few crops that can be grown at high elevations, making it a key resource within the Tibet Plateau. Weeds are a significant threat to highland barley production and new herbicides and tolerant barley varieties are needed to control this ever-growing problem. Results: A better understanding of existing herbicide resistance mechanisms is therefore needed. In this study, transcriptomic and metabolomic analyses were used to identify molecular and physiological changes in two highland barley genotypes with differing sensitivities to pyroxsulam. We identified several stress-responsive metabolites, including flavonoids and antioxidants, which accumulated to significantly higher levels in the pyroxsulam-resistant genotype. Additionally, we found key genes in both the flavonoid biosynthesis pathway and the antioxidant system were up-regulated in pyroxsulam-resistant barley. Conclusions: This work significantly expands on the current understanding of the molecular mechanisms underlying differing pyroxsulam tolerance among barley genotypes and provides several new avenues to explore for breeding or engineering tolerant barley.

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Recent advances in 1,2,4-triazolo[1,5-a]pyrimidine chemistry

Cited by 29 publications

References 381 publications

Benzimidazoazapurines: Design, Synthesis, and Photophysical Study

Benzimidazoazapurines: Design, Synthesis, and Photophysical Study

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

Integrated Transcriptomic and Metabolomic Analyses of the Molecular Mechanisms of Two Highland Barley Genotypes with Differential Pyroxsulam Responses

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