Triazine Nucleus Research Articles

An Acid-Responsive Fluorescent Molecule for Erasable Anti-Counterfeiting.

A tetraphenylethylene (TPE) derivative, TPEPhDAT, modified by diaminotriazine (DAT), was prepared by successive Suzuki-Miyaura coupling and ring-closing reactions. This compound exhibits aggregation-induced emission enhancement (AIEE) properties in the DMSO/MeOH system, with a fluorescence emission intensity in the aggregated state that is 5-fold higher than that of its counterpart in a dilute solution. Moreover, the DAT structure of the molecule is a good acceptor of protons; thus, the TPEPhDAT molecule exhibits acid-responsive fluorescence. TPEPhDAT was protonated by trifluoroacetic acid (TFA), leading to fluorescence quenching, which was reversibly restored by treatment with ammonia (on-off switch). Time-dependent density functional theory (TDDFT) computational studies have shown that protonation enhances the electron-withdrawing capacity of the triazine nucleus and reduces the bandgap. The protonated TPEPhDAT conformation became more distorted, and the fluorescence lifetime was attenuated, which may have produced a twisted intramolecular charge transfer (TICT) effect, leading to fluorescence redshift and quenching. MeOH can easily remove the protonated TPEPhDAT, and this acid-induced discoloration and erasable property can be applied in anti-counterfeiting.

Synthesis and Biological Evaluation of New Dithiocarbamate Derivatives and New α-aminophosphonate Conjugates Containing 1,3,5 Triazine Nucleus

Synthesis and Biological Evaluation of New Dithiocarbamate Derivatives and New α-aminophosphonate Conjugates Containing 1,3,5 Triazine Nucleus

Heterocyclic Compounds Bearing Triazine Scaffold and Their Biological Significance: A 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.

Spectroscopic and Electrochemical Investigations of New 5-oxo-2- Phenyloxazol-4(5H)-ylidene Based Triazine Derivatives

The present study reports the two step synthesis of a novel oxazolone derivative, 4-((4,6-bis(4-((Z)-(5-oxo-2-phenyloxazol-4(5H)-ylidene) methyl)phenoxy)-1,3,5-triazin-2-yl) oxy) benzaldehyde (CBOZ (5)), containing two oxazolone ring substituted with central triazine nucleus in their structural framework. The structural and spectroscopic properties of synthesized CBOZ (5) were characterized by FTIR, 1HNMR, 13CNMR, and mass spectroscopic analysis. The UV-Vis absorption of CBOZ (5) showed a single absorption band at ~370 nm due to π-π* transition with the estimated energy gap of ~3.02 eV. Cyclic voltammetry analysis revealed that the synthesized CBOZ (5) obtained the HOMO and LUMO values of -5.87 eV and-2.85 eV, respectively. Density functional theory (DFT) studies were carried out to predict the electronic absorption spectra of CBOZ (5) and the obtained values were in excellent agreement with the experimental results.

Novel Synthesis of Imidazo‐based and Benzimidazo‐based privileged Templates on s‐Triazine Nucleus through a Phenoxyl Spacer

A novel synthetic procedure has been designed for the synthesis of imidazo‐based and benzimidazo‐based privileged templates on s‐triazine nucleus through a phenoxyl spacer by exploiting the versatility of the reactive synthon imidate ester.

A New Approach for the Synthesis of Chalcone, Acetyl Pyrazoline and Amino Pyrimidine Bearing 1,3,5- Triazine Nucleus as Potential Antimicrobial and Antitubercular Agent

In an attempt to find a new class of antimicrobial and antitubercular agent, a new series of chalcone, acetyl pyrazoline and amino pyrimidine bearing 1,3,5- triazine nucleus were synthesized with appropriate chemical reagent. Chalcones (D 1 -D 5 ) were synthesized by the classical Claisen-Schmidt condensation of substituted ketone (C) with variously substituted aldehydes via conventional method. Now treatment of chalcones with hydrazine hydrate/glacial acetic acid and guanidine hydrochloride/Alkali afforded the corresponding acetyl pyrazoline (E 1 -E 5 ) and amino pyrimidine (F 1 -F 5 ) derivatives respectively. The chemical structures of all newly synthesized compounds were established on the basis of their FTIR, 1H NMR, 13C NMR, LC-MS as well as elemental analysis. All the newly design compounds were assayed for their in vitro antimicrobial activity against selected pathogens by the Broth dilution method and in vitro antitubercular activity against Mycobacterium tuberculosis H 37 Rv using Lowenstein-Jensen MIC method. Most of the compounds showed appreciable antimicrobial activity against the all tested strains. Among the synthesized compounds D 1 , D 2 , D 3 , E1, E3, E4, F3 and F4 exhibited excellent antimicrobial activity and said to be the most proficient members of the series. Compound D 5 and F 5 exhibited promising antitubercular activity.

Bisaminoferrocenyl triazine derivatives: effects of the third substituent on the extent of interaction between the metal centers

We prepared a new series of bisaminoferrocenyl triazine derivatives and investigated their anodic voltammetric behavior. The electronic nature of the third substituent on the triazine nucleus, that is, its electronic donor/acceptor character determines the level of interactions between the two ferrocenyl centers as measured by the separation between their two oxidation half-wave potentials.

Synthesis of pyrazolo[1,5-a][1,3,5]triazine derivatives as inhibitors of thymidine phosphorylase

Thymidine phosphorylase (TP) is an enzyme that promotes tumor growth and metastasis and therefore is an attractive druggable target. Using a reported TP inhibitor, 7-deazaxanthine (7DX), as the lead compound; this study was set up to evaluate whether pyrazolo[1,5-a][1,3,5]triazin-2,4-diones and pyrazolo[1,5-a][1,3,5]triazin-2-thioxo-4-ones would exhibit TP inhibitory activity. The pyrazolo[1,5-a][1,3,5]triazine nucleus was constructed using a reaction that annulated the 1,3,5-triazine ring onto a pyrazole scaffold. Among the 52 compounds synthesized and tested, it was found that 1,3-dihydro-pyrazolo[1,5-a][1,3,5]triazin-2-thioxo-4-ones exhibited various extent of inhibitory activity against TP. The best compound 17p, which bears a para-substituted pentafluorosulfur group, showed an IC50 value of 0.04 μM, which was around 800 times more potent than the 7DX (IC50 = 32 μM) under the same bioassay conditions. The results of the study suggested that a substituent with +σ and +π properties inserted at position 4 of a phenyl ring that is attached to position 8 of the pyrazolo[1,5-a][1,3,5]triazin-2-thioxo-4-one scaffold would give excellent TP inhibitory action. In addition, 17p was found to be a non-competitive inhibitor thus suggested that it might interact with TP at a position different from the substrate binding site.

Multiple hydrogen bonded mesomorphic complexes between complementary 1,3,5-triazine and pyrimidine derivatives

A 2,4-diamino-6-phenyl-1,3,5-triazine grafted with two semiperfluorinated chains at the phenyl substituent has been investigated in binary mixtures with complementary orotic acid and barbituric acid derivatives carrying either a lipophilic alkyl or a semiperfluoroalkyl tail. Equimolar mixtures of the triazine with nucleobases form triple hydrogen-bonded heterodimers with an elongated central core. Mesomorphic properties are observed only if the pyrimidinone component provides an additional free NH function not involved in triple H-bonding with the triazine nucleus. In that case, additional H-bond interactions orthogonal to the rod-shaped core of the heterodimers initiate the formation of cyclotrimeric rosette-type associates with circular geometry of the polar core region. Rosettes of heterodimers involving an alkyl substituted nucleobase organize to hexagonal columnar mesophases. Replacing the alkyl tail of the pyrimidine with a semiperfluorinated fragment leads to the formation of a micellar cubic phase. The individual micelles are composed of segmented columns three-dimensionally surrounded by a continuum of the semiperfluorinated segments.

Development of a Practical Synthesis of a Functionalized Pyrrolo[2,1-f][1,2,4]triazine Nucleus

Functionalized pyrrolotriazine 1b is a key heterocyclic building block in the synthesis of BMS-690514, a potent anticancer agent. Described herein are our development activities that led to the efficient preparation of 1b on a large scale. The key transformations include a selective C-alkylation of an oxalacetate salt with a hydrazonyl bromide to form a 2-hydrazonoethyl-3-oxosuccinate, followed by cyclodehydration to an aminopyrrole. Subsequent deprotection and condensation with formamidine afforded the pyrrolotriazine scaffold. Further elaboration of this core provided the desired pyrrolotriazinyl amine.

3D-QSAR studies on purine-carbonitriles as cruzain inhibitors: comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA)

Cruzain has been identified as the major cysteine protease of Trypanosoma cruzi, the etiological cause of Chaga's disease. For this reason, many efforts have been undertaken to design new inhibitors against this enzyme. Recently, molecules having a purine or triazine nucleus have been reported as potent non-peptidic inhibitors of cruzain. In order to gain an insight into the structural requirements that can lead to the improvement of the activity of these molecules, in this paper we report the CoMFA and CoMSIA studies of a series of purine-carbonitriles as cruzain inhibitors. Quantum semi-empirical calculations of the inhibitors inside the active site of cruzain were used as an approach to obtain reliable conformations for molecular alignment. Two different molecular alignments were used, resulting in 3 CoMFA models and 31 CoMSIA models. These models correspond to all of the possible combinations among five fields: steric, electrostatic, hydrophobic, hydrogen bond donor, and hydrogen bond acceptor. Highly predictive models were obtained. Based on the q2 values, the best CoMFA model had an r2 = 0.98 and a q2 = 0.73, whereas the best CoMSIA model retrieved an r2 = 0.88 and a q2 = 0.62. All models were validated with a rigorous procedure using an external test set. Contour maps obtained from these models show a preference toward the purine ring and indicate that bulky groups with a negative potential at the 3- and 5-positions of the phenyl ring are important structural requirements for inhibitory activity against cruzain.

ChemInform Abstract: Efficient Synthesis of Some Novel Spiro Heterocycles Containing Triazine Nucleus and Their Microbiological Activity.

AbstractTitle compounds (VIII) and (X) are screened for microbiological activity.

Collagen stabilization and modification using a polyepoxide, triglycidyl isocyanurate

This paper reports a study on the crosslinking behaviour of dermal collagen with the polyepoxide triglycidyl isocyanurate (TEPIC), which is thought to introduce a specific stabilization effect into a collagen matrix. TEPIC shows a higher reactivity towards collagen compared to glycerol triglycidyl ether, a water-soluble epoxide with the same tri-functionality but having an aliphatic backbone in its molecular structure, and one of the most commonly used epoxide monomers reported in the literature. Significant stabilization of the collagen matrix treated with TEPIC has been shown in our work, based on the examination of hydrothermal properties, thermal degradation and enzyme degradation properties, amino acid analysis and measurement of mechanical properties. Collagen's dimensional stability was also found to be improved, from tensile testing and fibre morphology observations (here by scanning electron microscopy). The overall stabilization effect of TEPIC is comparable or better than the conventionally used crosslinker, glutaraldehyde, and so implies that a stable three-dimensional, covalent network is formed by the TEPIC within the collagen supermolecule, instead of the two-dimensional crosslinked bridging systems in the case of glutaraldehyde. These results also suggest that the additional stabilization by TEPIC may relate to its triazine nucleus, which introduces a more rigid conformation into the collagen polypeptide chains. In addition, the treated collagen matrix has been found to have increased adsorption ability for anionic dyes. This study has shown that TEPIC can be considered as one of the more effective aldehyde alternatives, which could have a potential significance in leather and textile industrial applications.

7-Dimethylamino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine methanol solvate

7-Dimethyl­amino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine crystallized with one mol­ecule of methanol to give the title compound, C12H13N7·CH3OH. The triazolo[1,5-a][1,3,5]triazine heterocyclic core is essentially planar as are both amino groups that are involved in π-electron delocalization with the triazolo[1,5-a][1,3,5]triazine nucleus. The methyl groups of the dimethyl­amino fragment are involved in the formation of weak intra­molecular C—H⋯N hydrogen bonds with the N atoms of the heterocyclic system. The crystal packing is stabilized by inter­molecular N—H⋯N hydrogen bonds between the triazolo[1,5-a][1,3,5]triazine mol­ecules. The methanol solvent mol­ecule also participates in the formation of the crystal structure via inter­molecular O—H⋯N, N—H⋯O and weak C—H⋯O hydrogen bonds, linking the layers of triazolo[1,5-a][1,3,5]triazine mol­ecules.

A New Series of Dendrimers Containing Two Ferrocenyl Units and a Fréchet Dendron around a Triazine Nucleus

The preparation and characterization of a new series of dendrimers containing two identical aminoferrocenyl units and a Fréchet dendron around a triazine nucleus is described. A sizable degree of electronic communication between the two redox active ferrocenyl residues was detected in dichloromethane solution containing tetrabutylammonium tetra(pentafluorophenyl)borate as the supporting electrolyte. Binding of glutarimide via hydrogen bonding interactions to all the dendrimers was easily detected by using (1)H NMR spectroscopic and voltammetric techniques.

The triazine ring as a scaffold for the synthesis of new organogelators

The synthesis of new organogelators based on a triazine nucleus is described together with the analysis of the properties of the main compound 15. This compound revealed an efficient organogelator in both polar and apolar solvents and represents a promising precursor of other functionalized organogelators.

1,2,4‐Triazolo[1,5‐a][1,3,5]triazines (5‐Azapurines): Synthesis and Biological Activity

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

1,2,4-Triazolo[1,5-a][1,3,5]triazines (5-Azapurines): Synthesis and Biological Activity

The present review gives an account of the various synthetic routes to the 5-aza-analogue of purine-1,2,4-triazolo[1,5-a][1,3,5]triazine nucleus and polyfused systems bearing this heterocyclic core. Data concerning biological activity of the compounds with l,2,4-triazolo[l,5-a][l,3,5]triazine skeleton are also discussed.

New dual inhibitors of EGFR and HER2 protein tyrosine kinases

A novel series of dual EGFR and HER2 inhibitors based on the pyrrolo[2,1- f][1,2,4]triazine nucleus is described. A general route toward their synthesis, which enables functionalization at multiple sites, has been developed. Biological evaluation in enzymatic and cell-based assays has identified a series of C-6 carbamates with potent biochemical and cellular activities.

Synthesis and SAR of 4-(3-hydroxyphenylamino)pyrrolo[2,1- f][1,2,4]triazine based VEGFR-2 kinase inhibitors

A versatile synthesis of the suitably functionalized pyrrolo[2,1- f][1,2,4]triazine nucleus is described. SAR at the C-5 and C-6 positions of the 4-(3-hydroxy-4-methylphenylamino)pyrrolo[2,1- f][1,2,4]triazine template led to compounds with good in vitro potency against VEGFR-2 kinase. Glucuronidation of the phenol group is mitigated by incorporation of a basic amino group on the C-6 side chain of the pyrrolotriazine nucleus.