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Current Topics in Medicinal Chemistry 20201,3,5-Triazine and azole can interact with various therapeutic targets, and their derivatives possess promising in vitro and in vivo anticancer activity. Hybrid... (Review)
Review
1,3,5-Triazine and azole can interact with various therapeutic targets, and their derivatives possess promising in vitro and in vivo anticancer activity. Hybrid molecules have the potential to enhance efficiency, overcome drug resistance and reduce side effects, and many hybrid molecules are under different phases of clinical trials, so hybridization of 1,3,5-triazine with azole may provide valuable therapeutic intervention for the treatment of cancer. Substantial efforts have been made to develop azole-containing 1,3,5-triazine hybrids as novel anticancer agents, and some of them exhibited excellent activity. This review emphasizes azole-containing 1,3,5-triazine hybrids with potential anticancer activity, and the structure-activity relationships as well as the mechanisms of action are also discussed to provide comprehensive and target-oriented information for the development of this kind of anticancer drugs.
Topics: Antineoplastic Agents; Azoles; Cell Proliferation; Cell Survival; Drug Screening Assays, Antitumor; Humans; Molecular Structure; Structure-Activity Relationship; Triazines
PubMed: 32156236
DOI: 10.2174/1568026620666200310122741 -
Topics in Current Chemistry (Cham) Jun 2022The molecules possessing triazine and tetrazine moieties belong to a special class of heterocyclic compounds. Both triazines and tetrazines are building blocks and have... (Review)
Review
The molecules possessing triazine and tetrazine moieties belong to a special class of heterocyclic compounds. Both triazines and tetrazines are building blocks and have provided a new dimension to the design of biologically important organic molecules. Several of their derivatives with fine-tuned electronic properties have been identified as multifunctional, adaptable, switchable, remarkably antifungal, anticancer, antiviral, antitumor, cardiotonic, anti-HIV, analgesic, anti-protozoal, etc. The objective of this review is to comprehensively describe the recent developments in synthesis, coordination properties, and various applications of triazine and tetrazine molecules. The rich literature demonstrates various synthetic routes for a variety of triazines and tetrazines through microwave-assisted, solid-phase, metal-based, [4+2] cycloaddition, and multicomponent one-pot reactions. Synthetic approaches contain linear, angular, and fused triazine and tetrazine heterocycles through a combinatorial method. Notably, the triazines and tetrazines undergo a variety of organic transformations, including electrophilic addition, coupling, nucleophilic displacement, and intramolecular cyclization. The mechanistic aspects of these heterocycles are discussed in a detailed way. The bioorthogonal application of these polyazines with various strained alkenes and alkynes provides a new prospect for investigations in chemical biology. This review systematically encapsulates the recent developments and challenges in the synthesis and possible potential applications of various triazine and tetrazine systems.
Topics: Alkenes; Alkynes; Cyclization; Cycloaddition Reaction; Triazines
PubMed: 35737142
DOI: 10.1007/s41061-022-00385-7 -
Topics in Current Chemistry (Cham) May 2021This review mainly focused on the synthesis and properties of triazine-based materials as well as the state-of-the-art development of these materials in adsorption-based... (Review)
Review
This review mainly focused on the synthesis and properties of triazine-based materials as well as the state-of-the-art development of these materials in adsorption-based extraction techniques in the past 5 years, such as solid-phase extraction, magnetic solid-phase extraction, solid-phase microextraction and stir bar sorptive extraction, and the detection of various pollutants, including metal ions, drugs, estrogens, nitroaromatics, pesticides, phenols, polycyclic aromatic hydrocarbons and parabens. In the triazine-functionalized composites, triazine-based polymers and covalent triazine frameworks have been developed as the adsorbents with potential for environmental pollutants, mainly relying on the large surface area and the affinity of triazinyl groups with the targets. Triazine-based adsorbents have satisfactory sensitivity and selectivity towards different types of analytes, attributed from various mechanisms including π-π, electrostatics, hydrogen bonds, and hydrophobic and hydrophilic effects. The prospects of the materials for adsorption-based extraction were also presented, which can offer an outlook for the further development and applications.
Topics: Adsorption; Chemical Fractionation; Cosmetics; Environmental Pollutants; Pharmaceutical Preparations; Triazines
PubMed: 33945059
DOI: 10.1007/s41061-021-00336-8 -
ChemistryOpen Jan 2023Heterocyclic systems are now considered to be an integral part of material chemistry. Thiophene, selenophene, furan, pyrrole, carbazole, triazine and others are some... (Review)
Review
Heterocyclic systems are now considered to be an integral part of material chemistry. Thiophene, selenophene, furan, pyrrole, carbazole, triazine and others are some such examples worth mentioning. 2,4,6-Tri(thiophen-2-yl)-1,3,5-triazine is a C -symmetric system with thiophene as the donor unit and s-triazine as the acceptor unit. This review gives an insight into the advances made in the thienyl-triazine chemistry over the past two to three decades. The synthetic pathways for arriving at this system and all its important derivatives are provided. The major focus is on the materials synthesized using the thienyl-triazine system, including star molecules, linear and hyperbranched polymers, porous materials and their diverse applications. This review will play a catalytic role for new dimensions to be explored in thienyl-triazine chemistry.
Topics: Thiophenes; Triazines; Polymers; Catalysis; Porosity
PubMed: 36599693
DOI: 10.1002/open.202200203 -
Anti-cancer Agents in Medicinal... 2020Benzene is a six-membered hydrocarbon ring system and if three carbon-hydrogen units of benzene ring are replaced by nitrogen atoms then triazine is formed. Triazines... (Review)
Review
Benzene is a six-membered hydrocarbon ring system and if three carbon-hydrogen units of benzene ring are replaced by nitrogen atoms then triazine is formed. Triazines are present in three isomeric forms 1,2,3- triazine, 1,2,4-triazine, and 1,3,5-triazine according to the position of the nitrogen atom. These are weak bases having weaker resonance energy than benzene, so nucleophilic substitution is preferred than electrophilic substitution. Triazine is an interesting class of heterocyclic compounds in medicinal chemistry. Numerous synthetic derivatives of triazine have been prepared and evaluated for a wide spectrum of biological activities in different models with desired findings such as antibacterial, antifungal, anti-cancer, antiviral, antimalarial, antiinflammatory, antiulcer, anticonvulsant, antimicrobial, insecticidal and herbicidal agents. Triazine analogs have exposed potent pharmacological activity. So, triazine nucleus may be considered as an interesting core moiety for researchers for the development of future drugs.
Topics: Anti-Infective Agents; Anti-Inflammatory Agents, Non-Steroidal; Antimalarials; Antineoplastic Agents; Heterocyclic Compounds; Humans; Molecular Structure; Triazines
PubMed: 31746306
DOI: 10.2174/1871520619666191028111351 -
Mini Reviews in Medicinal Chemistry 2020Triazine is the six-membered heterocyclic ring containing three nitrogens, which replace the carbon-hydrogen unit in the benzene ring. Based on nitrogen position present... (Review)
Review
Triazine is the six-membered heterocyclic ring containing three nitrogens, which replace the carbon-hydrogen unit in the benzene ring. Based on nitrogen position present in the ring system, it is categorized in three isomeric forms, i.e., 1, 2, 3-triazine (vicinal triazine), 1, 2, 4-triazine (asymmetrical triazine or isotriazine) and 1, 3, 5-triazine (symmetrical or s-triazine or cyanidine). Triazines have a weakly basic property. Their isomers have much weaker resonance energy than benzene structure, so nucleophilic substitution reactions are more preferred than electrophilic substitution reactions. Triazine isomers and their derivatives are known to play important roles possessing various activities in medicinal and agricultural fields such as anti-cancer, antiviral, fungicidal, insecticidal, bactericidal, herbicidal, antimalarial and antimicrobial agents.
Topics: Anti-Infective Agents; Antineoplastic Agents; Bacteria; Fungi; Humans; Insecticides; Neoplasms; Triazines
PubMed: 32727324
DOI: 10.2174/1389557520666200729160720 -
Spectrochimica Acta. Part A, Molecular... Apr 2015Crystal structure of the title compound, C26H21N3O5, has been synthesized and characterized by FT-IR, (1)H NMR, (13)C NMR and X-ray single crystal determination. The... (Review)
Review
Crystal structure of the title compound, C26H21N3O5, has been synthesized and characterized by FT-IR, (1)H NMR, (13)C NMR and X-ray single crystal determination. The molecular geometry was also calculated by using Gaussian 03 software and structure was optimized by using HF and DFT/B3LYP method with the 6-31G(d) basis sets in ground state. The comparison of the theoretical and experimental geometries of the title compound indicated that the X-ray parameters agree with the theoretically obtained values. It was seen that R(2) value changes from 0.015 to 0.021 Å for bond length and angle. The calculated vibrational frequencies are also in good agreement with the experimental results. The (1)H and (13)C NMR chemical shifts values of (E)-2-(2-hydroxystyryl)-6-(4-methoxybenzoyl)-5-(4-methoxyphenyl)-1,2,4-triazin-3(2H)-one molecule have been calculated by the GIAO method. Besides, molecular electrostatic potential maps (MEP), Mulliken charges and Nonlinear Optical effects (NLO) analysis of the compound have been calculated by the HF and B3LYP/6-31G(d) methods.
Topics: Carbon-13 Magnetic Resonance Spectroscopy; Crystallography, X-Ray; Electrons; Hydrogen Bonding; Models, Molecular; Molecular Conformation; Nonlinear Dynamics; Proton Magnetic Resonance Spectroscopy; Spectroscopy, Fourier Transform Infrared; Static Electricity; Thermodynamics; Triazines; Vibration
PubMed: 25704130
DOI: 10.1016/j.saa.2015.01.056 -
Chemical Reviews Dec 2021Triazines are an important class of six-membered aromatic heterocycles possessing three nitrogen atoms, resulting in three types of regio-isomers: 1,2,4-triazines... (Review)
Review
Triazines are an important class of six-membered aromatic heterocycles possessing three nitrogen atoms, resulting in three types of regio-isomers: 1,2,4-triazines (-triazines), 1,2,3-triazines (-triazines), and 1,3,5-triazines (-triazines). Notably, the application of triazines as cyclic aza-dienes in inverse electron-demand Diels-Alder (IEDDA) cycloaddition reactions has been established as a unique and powerful method in -heterocycle synthesis, natural product preparation, and bioorthogonal chemistry. In this review, we comprehensively summarize the advances in the construction of these triazines via annulation and ring-expansion reactions, especially emphasizing recent developments and challenges. The synthetic transformations of triazines are focused on IEDDA cycloaddition reactions, which have allowed access to a wide scope of heterocycles, including pyridines, carbolines, azepines, pyridazines, pyrazines, and pyrimidines. The utilization of triazine IEDDA reactions as key steps in natural product synthesis is also discussed. More importantly, a particular attention is paid on the bioorthogonal application of triazines in fast click ligation with various strained alkenes and alkynes, which opens a new opportunity for studying biomolecules in chemical biology.
Topics: Biological Products; Cyclization; Cycloaddition Reaction; Electrons; Triazines
PubMed: 34586777
DOI: 10.1021/acs.chemrev.1c00611 -
International Journal of Environmental... Apr 2022Wastewater treatment plants (WWTPs) represent a major point source for pesticide residue entry to aquatic environment and may threaten ecosystems and biodiversity in...
Wastewater treatment plants (WWTPs) represent a major point source for pesticide residue entry to aquatic environment and may threaten ecosystems and biodiversity in urban area. Triazine herbicides should be paid attention to for their ubiquitous occurrence in the environment and long-term residue. The present study aimed to quantify eleven compounds of triazine herbicides during wastewater treatment processes. The solid phase extraction and gas-chromatography mass spectrometry (GC-MS) determination method were developed to identify the target herbicides with approving sensitivity. The pollution levels, removal rates of eleven triazine herbicides along five different treatment stages in WWTP were investigated. The results showed that three herbicides including atrazine, simetryn and prometryn were detected. Their concentrations in influent were among 28.79 to 104.60 ng/L. Their total removal rates from influent to effluent were 14.92%, 10.79% and 4.41%, respectively indicating that they were difficult to be effectively remove during wastewater treatment. Regarding the negative impact of triazine herbicides discharged from WWTPs on downstream water quality and aquatic life, the environmental risks were assessed by calculating the Environmental Relevance of Pesticides from Wastewater Treatment Plants Index () and water cycle spreading index (). The risk assessment results denoted the possible high risks for atrazine and simetryn to alage, and simetryn concurrently posed a high risk for the daphnia, while prometryn was at medium risk to alage. Atrazine and simetryn in effluent posed high risk for algae, meanwhile, simetryn had high risk for Daphnia. These results suggested a possible threat to the aquatic environment, rendering in this way the method as a useful assessment tool. Further extensive study is needed for atrazine and simetryn in order to better understand their migration mechanism in aquatic environment.
Topics: Atrazine; Ecosystem; Environment; Environmental Monitoring; Herbicides; Prometryne; Triazines; Water Pollutants, Chemical; Water Purification
PubMed: 35457424
DOI: 10.3390/ijerph19084557 -
European Journal of Medicinal Chemistry Nov 2021Heterocyclic compounds create an important class of molecules that demonstrates various chemical spaces for the definition of effective medicines. Many N-heterocycles... (Review)
Review
Heterocyclic compounds create an important class of molecules that demonstrates various chemical spaces for the definition of effective medicines. Many N-heterocycles display numerous biological activities. Among condensed heterocycles, pyrazolotriazine derivatives have received the attention of researchers owing to the extensive spectrum of biological activities. The reactivity of identified compounds was similar to the free azoles and triazines. The pyrazolotriazine scaffold exhibited antiasthma, antiinflammatory, anticancer, antithrombogenic activity and showed activity for major depression and pathological anxiety. Pyrazolotriazine derivatives also exhibited antibacterial, anticancer, antimetabolites, antidiabetic, antiamoebic, anticonvulsant, antiproliferative activity, human carbonic anhydrase inhibition, cyclin-dependent kinase 2 inhibition, tyrosinase and urease inhibition, MAO-B inhibition, TTK inhibition, thymidine phosphorylase inhibition, tubulin polymerization inhibition, protoporphyrinogen oxidase inhibition, GABA agonistic activity, hCRF1 receptor antagonistic activity, and CGRP receptor antagonistic activity. This paper structurally categorized various pyrazolotriazines to isomeric classes into six groups that containing pyrazolo [1,5-d] [1,2,4] triazine, pyrazolo [5,1-c] [1,2,4] triazine, pyrazolo [3,4-e] [1,2,4] triazine, pyrazolo [4,3-e] [1,2,4] triazines, pyrazolo [1,5-a] [1,3,5] triazine, and pyrazolo [3,4-d] [1,2,3] triazine and expressed biological activity, the synthetic procedures for each class of pyrazolotriazines, structure-activity relationship and their mechanism of action. Generally, this review summarily indicated the past and present studies about the discovery of new lead compounds with good biological activity.
Topics: Animals; Humans; Molecular Structure; Pyrazoles; Structure-Activity Relationship; Triazines
PubMed: 34147747
DOI: 10.1016/j.ejmech.2021.113537