1,3,5-Triazines

Sonawane, Ravindra P.; Sikervar, Vikas; Sasmal, Swarnendu

doi:10.1016/b978-0-12-818655-8.00018-4

Cited by 7 publications

(5 citation statements)

References 179 publications

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“…The second chlorine atom of mono-substituted triazine could be replaced at low temperature to room temperature depending on the reactivity of the nucleophile. The third chlorine atom of the disubstituted triazine is generally replaced at higher temperatures (more than 60 °C) …”

Section: Resultsmentioning

confidence: 99%

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Novel Sulfonamide–Triazine Hybrid Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents

2023

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The biological benefits of trisubstituted 1,3,5-triazine derivatives include their ability to reduce inflammation and fight cancer. A unique series of sulfonamide− triazine hybrid molecules were produced chemically by synthesizing triazine derivatives utilizing the usual nucleophilic aromatic substitution of cyanuric chloride via the solventfree/neat fusion method. Fourier-transform infrared spectroscopy (FTIR), 1 H NMR, and 13 C NMR spectroscopic analyses were used to identify novel trisubstituted synthetic compounds. The synthesized compounds have a moderate inhibition percentage when tested at 100 μM against the phosphoinositol 3-kinases (PI3Kα) enzyme; compounds 20 and 34 showed 46 and 68% anti-PI3Kα activity, respectively. To comprehend the anticipated interactions, the most successful compounds were subsequently docked into a PI3Kα protein's binding site (PDB code: 6OAC, resolution: 3.15 Å). The final synthetic compounds' anticancer activity was tested on the breast (MCF-7) and lung (A549) cancer cell lines at doses of 100 and 50 μM for additional evaluation of anticancer characteristics. The IC 50 values for the sulfaguanidine−triazine derivatives 27, 28, 29, 31, and 35 ranged from 14.8 to 33.2 μM, showing that compounds containing sulfaguanidine and diethylamine in their structures significantly inhibited the activity. Compound 34 could be a promising lead compound for developing new target-selected anticancer compounds with low toxicity and high selectivity.

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Section: Resultsmentioning

confidence: 99%

“…The third chlorine atom of the disubstituted triazine is generally replaced at higher temperatures (more than 60 °C). 32 …”

Section: Resultsmentioning

confidence: 99%

Novel Sulfonamide–Triazine Hybrid Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents

2023

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“…1,3,5-triazine is, as well as benzene, a C3-symmetric core but also a π-deficient heterocycle. It is, therefore, liable to engage in face-to-face interactions, contrarily to T-shape edge-to-face interactions of benzene [ 40 ].…”

Section: Recent Work Concerning Novel C3-symmetric Drugsmentioning

confidence: 99%

C3-Symmetric Ligands in Drug Design: When the Target Controls the Aesthetics of the Drug

2023

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A number of proteins are able to adopt a homotrimeric spatial conformation. Among these structures, this feature appears as crucial for biologic targets, since it facilitates the design of C3-symmetric ligands that are especially suitable for displaying optimized ligand–target interactions and therapeutic benefits. Additionally, DNA as a therapeutic target, even if its conformation into a superhelix does not correspond to a C3-symmetry, can also take advantage of these C3-symmetric ligands for better interactions and therapeutic effects. For the moment, this opportunity appears to be under-exploited, but should become more frequent with the discovery of new homotrimeric targets such as the SARS-CoV2 spike protein. Besides their potential therapeutic interest, the synthetic access to these C3-symmetric ligands often leads to chemical challenges, although drug candidates with an aesthetic structure are generally obtained.

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“…Several AATs, such as atrazine, ametryn, and simazine, are utilized as high-production-volume chemicals in agricultural production . AATs are extensively used as antifouling biocides, chemical intermediates, pharmaceuticals, and paint additives, and certain analogues have been detected in various water bodies globally (e.g., surface water, groundwater, seawater, and drinking water), threatening aquatic life and human health. − For instance, prometryn posed site-specific effects on the local algal community in the river Elbe basin in Bitterfeld, Germany, via the mode of action (MoA) of photosynthesis inhibition by targeting photosystem II function. , Multiple toxic effects of AATs on humans are demonstrated, particularly endocrine-disrupting effects, reproductive and developmental toxicity, and organ toxicity. , …”

Section: Introductionmentioning

confidence: 99%

Occurrence and Ecological Risk of Alkylamine Triazines in Chinese Estuarine Sediments: An Emerging Class of Persistent, Mobile, and Toxic Substances

Li,

Su,

Zhong

et al. 2024

Environ. Sci. Technol.

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Identifying persistent, mobile, and toxic (PMT) substances from synthetic chemicals is critical for chemical management and ecological risk assessment. Inspired by the triazine analogues (e.g., atrazine and melamine) in the original European Union’s list of PMT substances, the occurrence and compositions of alkylamine triazines (AATs) in the estuarine sediments of main rivers along the eastern coast of China were comprehensively explored by an integrated strategy of target, suspect, and nontarget screening analysis. A total of 44 AATs were identified, of which 23 were confirmed by comparison with authentic standards. Among the remaining tentatively identified analogues, 18 were emerging pollutants not previously reported in the environment. Tri- and di-AATs were the dominant analogues, and varied geographic distributions of AATs were apparent in the investigated regions. Toxic unit calculations indicated that there were acute and chronic risks to algae from AATs on a large geographical scale, with the antifouling biocide cybutryne as a key driver. The assessment of physicochemical properties further revealed that more than half of the AATs could be categorized as potential PMT and very persistent and very mobile substances at the screening level. These results highlight that AATs are a class of PMT substances posing high ecological impacts on the aquatic environment and therefore require more attention.

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1,3,5-Triazines

Cited by 7 publications

References 179 publications

Novel Sulfonamide–Triazine Hybrid Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents

Novel Sulfonamide–Triazine Hybrid Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents

C3-Symmetric Ligands in Drug Design: When the Target Controls the Aesthetics of the Drug

Occurrence and Ecological Risk of Alkylamine Triazines in Chinese Estuarine Sediments: An Emerging Class of Persistent, Mobile, and Toxic Substances

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