Triazine Derivatives Research Articles

Synthesis of N‐Phenylazo (Triazine) Derivatives of 6‐Aminouracil Using Diazonium Salt Under Catalyst‐Free Condition

AbstractIn the current study, for the first time, N‐phenylazo (triazine) derivatives of 6‐aminouracil compounds were produced at room temperature under catalyst‐free conditions in pyridine using an easy, efficient, and green process. The main advantages of this approach are that it doesn't require a catalyst, is inexpensive, eco‐friendly, non‐toxic, and simple to handle. This technique shows a broad range of substrate compatibility for uracil compounds and diazonium salts.

Exploring the Anticancer Potential of Triazine Derivatives: An Outlook of Designing Strategies, Docking Studies, and Structure‐Activity Relationships (SAR)

AbstractCancer is a disease characterized by uncontrolled cell growth resulting from genetic and epigenetic changes accumulating within a cancer cell population. Despite the milestone discovery of chemotherapeutic drugs against cancer, cancer remains tough to cure. Therefore, cancer has the second‐highest global death rate. There are certain factors such as genetic mutation, cancer cell diversity, metastasis, and resistance, which limit chemotherapy. To combat cancer, it's crucial to find novel therapeutic tactics and produce novel drugs that target cancer cells without affecting healthy cells. Heterocyclic compounds influence certain molecular targets to find novel lead structures can be a noteworthy strategy for the development of potential anticancer agents. Triazine, a low‐cost and widely available heterocyclic scaffold, has piqued researchers’ interest in developing innovative designing strategies. This review presents the advancement of three different isomers of triazines as anticancer agents. The main focus of this review is to provide the advancement of designing strategies, structure‐activity relationships, and docking studies of triazine derivatives as anticancer agents the available triazine‐containing drugs, and the status of clinical trials of triazine‐containing drugs were also highlighted. Lastly, we have also concluded the most potent derivatives and their hybridization with another ring to justify the particular anticancer activity.

Triazine derivative as volatile solid additive for non‐halogenated solvent and thermal annealing‐free processed organic solar cells with over 18% efficiency

AbstractVolatile solid additive (VSA) has been demonstrated to be an effective strategy to optimize the morphology of the active layer for high‐performance organic solar cells (OSCs). Most of the reported OSCs with VSA are processed by chloroform (CF) and relies on thermal annealing (TA) posttreatment. However, the CF solvent problems of low boiling point, toxicity, and environmental‐unfriendly as well as increasing cost from TA restricted the large‐scale production. Here, a simple‐structured and low‐cost triazine derivative 2,4,6‐trichloro‐1,3,5‐triazine (TCT) as a VSA was introduced into PM6:BTP‐eC9‐based OSCs. Employing the TCT additive, the nonhalogenated solvent (o‐xylene) processed OSCs without TA treatment and delivered higher power conversion efficiencies (PCEs) in comparison to the TA‐treated counterpart. Benefiting from the intermolecular interactions between TCT and the active layer materials, the TCT‐treated blend films exhibited optimized morphology and enhanced crystallinity. As a result, the PM6:BTP‐eC9 OSCs achieved a champion PCE of 18.18% and fill factor (78.5%), which is among one of the most advanced nonhalogenated solvent‐processed and annealing‐free OSCs. Meanwhile, the TCT‐treated blend films also demonstrated the better photo‐stability compared to the control device. This work provides a guideline of triazine derivatives as VSA for high‐performance OSCs with TA‐free and nonhalogenated solvent‐processing treatment.

Asymmetric direct Aldol reaction between acetone and aromatic aldehydes catalyzed by diazadioxocalix[2]arene[2]triazine derivatives

Asymmetric direct Aldol reaction between acetone and aromatic aldehydes catalyzed by diazadioxocalix[2]arene[2]triazine derivatives

Multiple Energy Transfer Modes From o‐Carborane Dyad Induced by Synergetic Conformational Regulations and Intense Circularly Polarized Luminescence in Self‐Assembly Aggregates

AbstractPhotothermal modulated excited conformations in traditional optoelectronic materials have been extensively investigated for the manipulation of emissive properties. However, photoinduced molecular synergetic conformational changes, which are promising for controlling intramolecular energy transfer modes through molecular orbital breaking, are never been explored. Herein, a novel o‐carborane dyad composed of carbazole units as electron donors and triazine derivatives as electron acceptors is demonstrated to achieve conformation‐dependent emissions and abundant emissions via synergetic conformational changes. Notably, the resulting dyad exhibited multiple conformational changes that induced emissions through different energy transfer modes involved “through space” and “through bond.” Exactly, the electron spin from singlet to triplet state took a flip accompanied by molecular orbitals from π–π molecular orbitals in the space charge transfer style to π and σ molecular orbitals in the bond charge transfer mode. The circularly polarized luminescence (CPL) properties are systematically investigated, exhibiting intense CPL with large glum values. These results provide novel perspectives for elucidating the complicated emission changes in aggregated states, as well as unique perspectives on the relationship between molecular conformations, energy transfer modes, and molecular orbital breaking.

A Novel Synthesis of Substituted Benzo[1,2,4]triazine Derivatives via Copper-Catalyzed Intermolecular N-Arylation of 2-Iodoaniline and Hydrazonoyl Chlorides

AbstractIn this contribution, a speedy and direct approach for the synthesis of benzo[1,2,4]triazine derivatives via a copper-catalyzed intermolecular N-arylation of 2-iodoaniline and hydrazonoyl chlorides is described. The reaction proceeds in THF at room temperature with no need for any ligand. The use of simple and readily available starting materials, mild copper-catalytic reaction conditions, and good yields (72–92%) are remarkable specifications of this protocol.

Synthesis and Characterization of Triazine Derivatives as Important Heterocyclic Compounds and Study their Biological Activities

Reaction 0f (thioacetamide/ acetemide) with chloroacetyl chloride to produced N-acetyl-2-chloro (thiocetamide/acetamide), then subsequent reaction with thiosemicarbazide to form N-acetyl-2-(2-carbamothioyl hydrazinyl)thioacetamide/acetamide. Ring closure or Cyclization of these compounds in the presence of sodium hydroxide yield N-(3-mercapto-1,4-dihydro-1,2,4 -triazin-5-yl)ethanethioamide/acetamide. The aim of this contribution is synthesis wide range of triazin derivatives by using different methodologies. These new triazine derivatives will be confirmed by FT- IR, 1HNMR, 13CNMR spectra. Since this triazine ring are very important core in chemical structure of some therapeutic compounds, will be evaluated for biological activities against two types of bacteria and fungi.

Catalytic Performance of Chiral Tetraaza-Bridged Calix[4]arene[2]triazine Derivatives for Enantioselective Michael Reactions.

Novel chiral tetraaza-bridged calix[4]arene[2]triazine-based organocatalysts were synthesized and used for catalytic asymmetric Michael reaction of acetylacetone to various aromatic nitrostyrenes. Chiral subunits (R)- and (S)-1,2,3,4-tetrahydro-1-naphthylamine were attached to the tetraaza-bridged calix[4]arene[2]triazine platform in both enantiomeric forms. The R configuration of the major enantiomer of the Michael product was obtained when 3a was used as catalyst, and the S configuration was obtained when 3b was used as catalyst. This indicated that the configuration of the Michael product was controlled by the chiral calixarene moiety. The Michael adducts were obtained in excellent yields (91%) and enantioselectivities (98%).

Green Synthesis of the Triazine Derivatives and their Application for the Benign Electrocatalytic Reaction of Nitrate Reduction to Ammonia.

This work uses green sustainable reactions twice. Firstly, it is microwave synthesis: 2,4,6-tribiphenyl-4-yl-1,3,5-triazine and similar compounds were prepared in a closed microwave reactor in n-octane by the Friedel-Crafts reaction. Second, a hybrid electrocatalyst for the highly demanded electrochemical reaction of nitrate reduction to ammonia (NO3RR) was prepared based on this material. This reaction has great potential to replace the energy-intensive Haber-Bosch process, and in addition, has independent value for the elimination of nitrate contamination of water resources. As shown in the work, microwave synthesis is an eco-friendly method for the synthesis of complex organic compounds; fast, selective and with a high yield of the target product. The electrocatalyst deposited on the graphite electrode consisted of a layer of 2,4-bis([1,1'-biphenyl]-4-yl)-6-hydroxy-1,3,5-triazine and related compounds coated with cobalt oxide. The hybrid catalyst was firmly retained on the graphite electrode during NO3RR and the material showed impressive stability with almost no decrease in catalytic activity even after the fifth cycle. Both 2,4-bis([1,1'-biphenyl]-4-yl)-6-hydroxy-1,3,5-triazine and the catalyst based on this substance were characterized by SEM, XPS, XRD, UV-vis spectra, cyclic (and linear) voltammetry, and chronoamperometry. This work can serve as a starting point for the development of stable and durable electrocatalysts for NO3RR using triazine derivatives.

Efficient Photocatalytic System based on Schiff‐Base Type Hybrid Polymers for Energy Conversion and Water Treatment

AbstractIn this contribution, a new Schiff‐base hybrid cross‐linked polymer (TFPT‐SHCP) derived from triazine derivatives and silsesquioxanes was developed, and its photocatalytic performance was systematically investigated. Compared with traditional organic Schiff base catalysts, in TFPT‐SHCP, organic inorganic hybrid silsesquioxanes monomers at the molecular level can serve as a sturdy host backbone, bringing structural ultrastability to the final material. And their excellent strength and durability make them have good application prospects in water treatment. Furthermore, the introduction of triazine derivatives with excellent photoelectric performance and the construction of −C=N‐ result in excellent photocatalytic performance of TFPT‐SHCP. The as‐prepared TFPT‐SHCP exhibits excellent degradation capacity of various organic pollutants under visible light catalysis, with degradation rate constants for Congo Red (CR), rhodamine B (RB) and tetracycline hydrochloride (TH) reaching 0.302 min−1, 0.121 min−1, 0.161 min−1, respectively. Under simulated outdoor conditions, dye solutions with concentrations up to 500 ppm can be degraded to complete decolorization within 5 weeks. This work demonstrates the enormous potential of POSS‐based Schiff base materials as a platform for visible light catalysts, paving the way for the pre design and functionalization of related materials in the future.

Preparation of Some New Pyrazine and Triazine Derivatives and Study of their Antimicrobial and Anticancer activities

Preparation of Some New Pyrazine and Triazine Derivatives and Study of their Antimicrobial and Anticancer activities

Novel artesunate-metformin conjugate inhibits bladder cancer cell growth associated with Clusterin/SREBP1/FASN signaling pathway.

Bladder cancer remains the 10th most common cancer worldwide. In recent years, metformin has been found to have potential anti-bladder cancer activity while high concentration of IC50 at millimolar level is needed, which could not be reached by regular oral administration route. Thus, higher efficient agent is urgently demanded for clinically treating bladder cancer. Here, by conjugating artesunate to metformin, a novel artesunate-metformin dimer triazine derivative AM2 was designed and synthesized. The inhibitory effect of AM2 on bladder cancer cell line T24 and the mechanism underlying was determined. Anti-tumor activity of AM2 was assessed by MTT, cloning formation and wound healing assays. Decreasing effect of AM2 on lipogenesis was determined by oil red O staining. The protein expressions of Clusterin, SREBP1 and FASN in T24 cells were evaluated by Western blotting. The results show that AM2 significantly inhibited cell proliferation and migration at micromolar level, much higher than parental metformin. AM2 reduced lipogenesis and down-regulated the expressions of Clusterin, SREBP1 and FASN. These results suggest that AM2 inhibits the growth of bladder cancer cells T24 by inhibiting cellular lipogenesis associated with the Clusterin/SREBP1/FASN signaling pathway.

Bis(dimethylpyrazolyl)-aniline-s-triazine derivatives as efficient corrosion inhibitors for C-steel and computational studies.

4,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-N-phenyl-1,3,5-triazin-2-amine (PTA-1), N-(4-bromophenyl)-4,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,3,5-triazin-2-amine (PTA-2) and 4,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-N-(4-methoxyphenyl)-1,3,5-triazin-2-amine (PTA-3) were synthesized and characterized. Their corrosion inhibition of carbon C-steel in 0.25 M H2SO4 was studied by electrochemical impedance. The inhibition efficiency (IE%) of triazine was superior due to the cumulative inhibition of triazine core structure and pyrazole motif. Potentiodynamic polarizations suggested that s-triazine derivatives behave as mixed type inhibitors. The IE% values were 96.5% and 93.4% at 120 ppm for inhibitor PTA-2 and PTA-3 bearing -Br and -OCH3 groups on aniline, respectively. While PTA-1 without an electron donating group showed only 79.0% inhibition at 175 ppm. The adsorption of triazine derivatives followed Langmuir and Frumkin models. The values of adsorption equilibrium constant K°ads and free energy change ΔG°ads revealed that adsorption of inhibitor onto steel surface was favoured. A corrosion inhibition mechanism was proposed suggesting the presence of physical and chemical interactions. Density functional theory computational investigation corroborated nicely with the experimental results. Monte Carlo simulation revealed that the energy associated with the metal/adsorbate arrangement dE ads/dN i, for both forms of PTA-2 and PTA-3 with electron donating groups (-439.73 and -436.62 kcal mol-1) is higher than that of PTA-1 molecule (-428.73 kcal mol-1). This aligned with experimental inhibition efficiency results.

Synthesis and Reactions of 3‐Amino‐5,6‐Dimethyl‐l,2,4‐Triazine: DFT Studies, ADME Assay, and Molecular Docking on the new l,2,4‐Triazine Derivatives as Anticancer Agents.

AbstractTwo effective one‐pot synthesis procedures were proposed for the synthesis of 3‐amino‐5,6‐dimethyl‐l,2,4‐triazine under free solvent conditions; these methods included fusing the monohydrazide of biacetyl with either methyl carbamimidothioate (Method B) or cyanamide (Method C). Simple reaction conditions, an easy work‐up process, and facile separation characterize the ecologically friendly fusion process used in techniques B and C. The results from methods B and C indicated the existence of amino‐imino prototropic tautomerism. The triazine in method C had a different melting point and had unusual mass spectral behavior, suggesting that it was in the imino‐tautomer form, as opposed to the amino‐tautomer form discovered in procedure B. The strong electron‐withdrawing activity of the triazine ring appears to deactivate the 3‐amino group, which in turn triggers the production of additional triazine derivatives (3–12), with yields ranging from 54% to 82%. To characterize the structure of the newly synthesized compounds, 1H, 13C‐NMR, and mass spectrometry were employed. The compounds that were created underwent testing at the National Cancer Institute. According to the screening results, conjugates 9 and 10 were successful against most of the cancer cell line subpanels. With the use of DFT, we conducted theoretical studies on compounds 9 and 10. Topological studies, including ELF, LOL, and RDG, were used to identify the main binding sites and weak interactions of the target derivatives. The synthesized compounds that have promising properties are subjected to a pharmacological examination using Swiss‐ADME. Cox‐1 (PDB ID: 3KK6) is the target of molecular docking experiments that aim to identify the anticancer active site of the derivatives of interest.

A Survey of UV Filters Used in Sunscreen Cosmetics

The aim of this study was to determine the types of UV filters used in adult and children’s sunscreen products sold in Poland (part of the EU market) and their frequency of use. The INCI compositions of sunscreen products were collected and analyzed for the presence of UV filters. The study included 150 randomly selected preparations for adults (from 71 brands) and 50 for children (from 33 brands). The survey concerned the UV filters listed in Annex VI to Regulation (EC) No 1223/2009 of the European Parliament and Council of 30 November 2009 on cosmetic products. The most frequently used UV filters in the child sunscreens were triazine derivatives: bis-ethylhexyloxyphenol methoxyphenyl triazine (60.0%) and ethylhexyl triazone (52.0%), and ethylhexyl salicylate (46.0%), a derivative of salicylic acid. The most common in adult sunscreens were butyl methoxydibenzoylmethane (56.0%), a dibenzoylmethane derivative, followed by the salicylic acid derivative ethylhexyl salicylate (54.7%) and the triazine derivatives bis-ethylhexyloxyphenol methoxyphenyl triazine (54.7%) and ethylhexyl triazone (50.0%). Physical filters, including their nano and non-nano forms, were more popular in sunscreens for children, i.e., 50.0% (TiO2) and 22.0% (ZnO), than for adults: 21.3% (TiO2) and 6.7% (ZnO). For both adults and children, many cosmetic products contained four or five UV filters per preparation; however, the child preparations often used two UV filters. To summarize, the following UV filters dominate in photoprotectors for both adults and children: butyl methoxydibenzoylmethane, bis-ethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazone, ethylhexyl salicylate, and diethylamino hydroxybenzoyl hexyl benzoate.

Donor-acceptor type conjugated porous polymers based on benzotrithiophen and triazine derivatives: Effect of linkage unit on photocatalytic water splitting

Donor-acceptor conjugated polymers have received significant attention as the most promising photocatalysts for efficient photocatalytic hydrogen production (PHP). Nonetheless, achieving high photocatalytic PHP performance relies on molecular framework design and the judicious selection of different structural units. Herein, benzotrithiophene (BTT) and triazine derivatives were used as the basic units of organic polymers, and two conjugated porous polymers (CPPs) named as CP1 and CP2 were successfully synthesized by Stille coupling reaction. Compared with benzene as the linkage unit of triazine, it is evident that the incorporation of the thiophene unit in CP2 broadens its light response range, and promotes the generation of electrons/holes induced by light. Density functional theory (DFT) calculations and femtosecond transient absorption(fs-TA) spectroscopy reveal that CP2 effectively inhibits the photogenerated electron-hole pair recombination and promotes carrier transport. Remarkably, CP2 with Pt co-catalyst exhibited a notably superior PHP performance compared with that of CP1 polymer, which achieved an impressive hydrogen evolution rate (HER) of 21702.4 μmol/g/h, surpassing CP1 by approximately 3.7 times. This work provides a new tactic for enhancing the intrinsic PHP activity and reveals the underlying mechanism for the enhanced photocatalytic activity by regulating the different structural units of the donor-acceptor conjugated polymers.

Synthesis, biological activities, and molecular docking studies of triazolo[4,3-b]triazine derivatives as a novel class of α-glucosidase and α-amylase inhibitors.

In diabetes mellitus, amylase and glucosidase enzymes are the primary triggers. The main function of these enzymes is to break macromolecules into simple sugar units, which directly affect blood sugar levels by increasing blood permeability. To overcome this metabolic effect, there is a need for a potent and effective inhibitor capable of suppressing the enzymatic conversion of sugar macromolecules into their smaller units. Herein, we reported the discovery of a series of substituted triazolo[4,3-b][1,2,4]triazine derivatives as α-glucosidase and α-amylase inhibitors. All target compounds demonstrated significant inhibitory activities against α-glucosidase and α-amylase enzymes compared with acarbose as the positive control. The most potent compound 10k, 2-[(6-phenyl-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl)thio]-N-[4-(trifluoromethyl)phenyl]acetamide, demonstrated IC50 values of 31.87 and 24.64 nM against α-glucosidase and α-amylase enzymes, respectively. To study their mechanism of action, kinetic studies were also done, which determined the mode of inhibition of both enzymes. Molecular docking was used to confirm the binding interactions of the most active compounds.

In-vitro Evaluation of Triazine Scaffold for Anticancer Drug Development: A Review.

The widespread importance of the synthesis and modification of anticancer agents has given rise to many numbers of medicinal chemistry programs. In this regard, triazine derivatives have attracted attention due to their remarkable activity against a wide range of cancer cells. This evaluation covers work reports to define the anticancer activity, the most active synthesized compound for the target, the SAR and, when described, the probable MOA besides similarly considered to deliver complete and target-pointed data for the development of types of anti-tumour medicines of triazine derivatives. Triazine scaffold for the development of anticancer analogues. Triazine can also relate to numerous beneficial targets, and their analogues have auspicious in-vitro and in-vivo anti-tumour activity. Fused molecules can improve efficacy, and drug resistance and diminish side effects, and numerous hybrid molecules are beneath diverse stages of clinical trials, so hybrid derivatives of triazine may offer valuable therapeutic involvement for the dealing of tumours. The objective of the recent review was to summarize the recent reports on triazine as well as its analogues with respect to its anticancer therapeutic potential. The content of the review would be helpful to update the researchers working towards the synthesis and designing of new molecules for the treatment of various types of cancer disease with the recent molecules that have been produced from the triazine scaffold. Triazine scaffolds based on 1,3,5-triazine considerably boost molecular diversity levels and enable covering chemical space in key medicinal chemistry fields.

Effects of solvent casted poly (lactic acid)/poly(ethylene glycol)/paraben derivative triazine films on antibacterial performance and cytotoxicity

AbstractA series of poly(lactic acid) (PLA) films that including fully paraben substituted triazine derivatives having anti‐bacterial properties have been prepared by utilizing the solvent‐casting method. PLA as biodegradable polymer, poly(ethylene glycol) (PEG) as a plasticizing agent and s‐triazine molecules (TA01, TA02, TA03, TA04, and TA05) behaving as an anti‐bacterial component have been utilized in the experiments. The influence of TA compounds on the antibacterial performance of PLA/PEG films was investigated for the first time against Gram‐negative Escherichia coli (E. coli) and Gram‐positive Staphylococcus aureus (S. aureus) bacteria via the contact active method. TA01‐03‐05 incorporated PLA/PEG films gave the best results against E.coli bacteria and log10 reductions of these films were 0.78, 0.64, and 0.65 respectively. The effect of TA compounds on the cell viability was investigated against cancer and non‐cancerous cell lines using an MTS assay. The results showed that TA compounds had a positive effect on cell growth in non‐cancerous cells, while they had a negative effect on cell growth in cancer cells. Furthermore, the addition of TA considerably increased the decomposition temperatures from 349° to 361° and char yield from 0.65 for PLA/PEG film to 2.3 for PLA/PEG/TA05. All of the films had good transparency and low opacity which was 7.2 for pure PLA used for control and the maximum opacity value was 11.2 observed for PLA/PEG/01. TA03 and TA04 caused a decrement of water vapor permission when compared to PLA/PEG films from 1439 to 749 and 664. It was also observed that pure PLA/PEG film lost weight rapidly over time during degradation tests. On the other hand, weight loss wasn't observed in PLA/PEG/TA films. This study focused on demonstrating the use of our new, flexible PLA/PEG derivatives in food and medical packaging.

A materials informatics driven fine-tuning of triazine-based electron-transport layer for organic light-emitting devices

Materials informatics in the development of organic light-emitting diode (OLED) related materials have been performed and exhibited the effectiveness for finding promising compounds with a desired property. However, the molecular structure optimization of the promising compounds through the conventional approach, namely the fine-tuning of molecules, still involves a significant amount of trial and error. This is because it is challenging to endow a single molecule with all the properties required for practical applications. The present work focused on fine-tuning triazine-based electron-transport materials using machine learning (ML) techniques. The prediction models based on localized datasets containing only triazine derivatives showed high prediction accuracy. The descriptors from density functional theory calculations enhanced the prediction of the glass transition temperature. The proposed multistep virtual screening approach extracted the promising triazine derivatives with the coexistence of higher electron mobility and glass transition temperature. Nine selected triazine compounds from 3,670,000 of the initial search space were synthesized and used as the electron transport layer for practical OLED devices. Their observed properties matched the predicted properties, and they enhanced the current efficiency and lifetime of the device. This paper provides a successful model for the ML assisted fine-tuning that effectively accelerates the development of practical materials.