Browse
Submit Data
Databases
API
Help

Dataset Information

25 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties.

ABSTRACT: A series of new symmetrical s-tetrazine derivatives, coupled via a 1,4-phenylene linkage with a 4H-1,2,4-triazole ring, were obtained. The combination of these two rings in an extensively coupled system has significant potential applications, mainly in optoelectronics. The methodology used turned out to be useful regardless of the type of five-membered ring or the nature of the individual substituents. All the products were identified by spectroscopic methods, and the target compounds were tested for luminescent properties. This study showed that all the synthesized highly-conjugated triazoles exhibited luminescence; in particular, one derivative, 3,6-bis(4-(5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazol-3-yl)phenyl)-1,2,4,5-tetrazine (13b), showed strong fluorescence emission and ahigh quantum yield close to 1.

SUBMITTER: Maj A

PROVIDER: S-EPMC8779062 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Highly Luminescent 4H-1,2,4-Triazole Derivatives: Synthesis, Molecular Structure and Photophysical Properties.

Project description:An alternative approach to the Suzuki cross-coupling reaction is used to synthesize a series of new luminophores based on 4-alkyl-4H-1,2,4-triazole cores conjugated via 1,4-phenylene linker to fused-bicyclic and tricyclic aromatic, or heteroaromatic arrangements. The described methodology allows one to conduct the coupling reaction with the use of commercially available boronic acids in the presence of conventional solvents or ionic liquids and produced excellent yields. It was found that the use of ultrasounds or microwaves significantly accelerates the reaction. The obtained compounds exhibited high luminescent properties and a large quantum yield of emitted photons. The X-ray molecular structures of three highly conjugated 4H-1,2,4-triazole representatives are also presented.

| S-EPMC7764194 | biostudies-literature

Synthesis of 4-Alkyl-4H-1,2,4-triazole Derivatives by Suzuki Cross-coupling Reactions and Their Luminescence Properties.

Project description:New derivatives of 4-alkyl-3,5-diaryl-4H-1,2,4-triazole were synthesized utilizing the Suzuki cross-coupling reaction. The presented methodology comprises of the preparation of bromine-containing 4-alkyl-4H-1,2,4-triazoles and their coupling with different commercially available boronic acids in the presence of ionic liquids or in conventional solvents. The obtained compounds were tested for their luminescence properties.

| S-EPMC6384732 | biostudies-literature

4-Amino-3,5-dimethyl-4H-1,2,4-triazole.

Project description:In the title compound, C(4)H(8)N(4), inter-molecular N-H?N hydrogen bonds involving the amino groups and triazole N atoms form a two-dimensional sheet.

| S-EPMC2961470 | biostudies-literature

Design, Synthesis, and Biological Evaluation of 1,2,4-Thiadiazole-1,2,4-Triazole Derivatives Bearing Amide Functionality as Anticancer Agents.

Project description:A novel library of amide functionality having 1,2,4-thiadiazole-1,2,4-triazole (8a-j) analogs was designed, synthesized, and structures were characterized by 1H NMR, 13C NMR, and mass (ESI-MS) spectral data. Further, all compounds were evaluated for their anticancer activities against four different cancer cell lines including breast cancer (MCF-7, MDA MB-231), lung cancer (A549), and prostate cancer (DU-145) by MTT reduction assay method, and etoposide acts as a standard drug. The results confirmed that majority of the synthesized compounds showed moderate to potent anticancer activities aligned with four cell lines. Among the synthesized compounds, 8b, 8c, 8d, 8e, 8g and 8i displayed more potent activity along with inhibitory concentration values ranging from 0.10 ± 0.084 to 11.5 ± 6.49 µM than the standard IC50 values, which ranges from 1.91 ± 0.84 to 3.08 ± 0.135 µM, respectively.

| S-EPMC7243954 | biostudies-literature

Synthesis, Characterization, and Enzyme Inhibition Properties of 1,2,4-Triazole Bearing Azinane Analogues.

Project description:Considering the importance of acetylcholine esterase (AChE, BchE) and α-glucosidase in the treatment of Alzheimer's disease and diabetes mellitus, the synthesis of novel azinane triazole-based derivatives as effective acetylcholinesterase (AchE), α-glucosidase, urease, lipoxygenase (LOX), and butyrylcholinesterase (BChE) inhibitors is described. Azinane analogue (2) was merged with 1,2,4-triazole to acquire 1-(4-toluenesulfonyl)-4-(3-mercapto-4-methyl-4H-1,2,4-triazol-5-yl) piperidine (8) through a list of intermediates including 1-(4-toluenesulfonyl)-4-(ethoxycarbonyl) piperidine (3), 1-(4-toluenesulfonyl)-4-(2-hydrazinocarbonyl)piperidine (5), and 1-(4-toluenesulfonyl)-4-[1-(methyl amino thiocarbonyl)-2-hydrazinocarbonyl]piperidine (7). The target molecules, 1-(4-toluenesulfonyl)-4-[3-(N-alkyl/phenyl/aryl-2-ethanamoyl thio)-4-methyl-4H-1,2,4-triazol-5-yl] piperidine (12a-o), were achieved through the reaction of 8 with N-alkyl/phenyl/aryl-2-bromo ethanamides (11a-o) as electrophiles. These electrophiles were accomplished by a benign reaction of alkyl/phenyl/aryl amines (9a-o) and 2-bromo ethanoyl bromide (10). The spectral study of IR, 1D-NMR, and EI-MS corroborated the synthesized compounds. Methyl phenyl and methyl phenyl-substituted derivatives 12d and 12m with IC50 = 0.73 ± 0.54; 36.74 ± 1.24; 19.35 ± 1.28; 0.017 ± 0.53; and 0.038 ± 0.50 μM are found to be the most potent AChE, α-glucosidase, urease, and BChE inhibitors. The high inhibition potential of synthesized molecules against AChE, α-glucosidase, urease, and BChEenzymes inferred their role in enzyme inhibition properties.

| S-EPMC9476189 | biostudies-literature

5-Amino-3-(4H-1,2,4-triazol-4-yl)-1H-1,2,4-triazole.

Project description:The asymmetric unit of the title compound, C(4)H(5)N(7), comprises two independent but virtually superimposable mol-ecules. Each mol-ecule is planar with the dihedral angles between the five-membered rings being 2.8?(3) and 2.1?(3)°. The crystal structure is formed by an extensive network of relatively strong N-H?N hydrogen-bond inter-actions. Individual mol-ecules are arranged into supra-molecular zigzag chains running parallel to [001] by way of the strongest N-H?N inter-actions. Adjacent chains are inter-connected by rather long (D?A distances range from ca 3.00 to 3.03?Å) but highly directional (inter-action angles above ca 173°) hydrogen bonds forming a supra-molecular layer in the bc plane.

| S-EPMC3435720 | biostudies-literature

Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety.

Project description:Seventeen novel 2-(5-amino-1-(substituted sulfonyl)-1H-1,2,4-triazol-3-ylthio)-6- isopropyl-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one compounds were synthesized from the abundant and naturally renewable longifolene and their structures were confirmed by FT-IR, NMR, and ESI-MS. The in vitro cytotoxicity of the synthesized compounds was evaluated by standard MTT assay against five human cancer cell lines, i.e., T-24, MCF-7, HepG2, A549, and HT-29. As a result, compounds 6d, 6g, and 6h exhibited better and more broad-spectrum anticancer activity against almost all the tested cancer cell lines than that of the positive control, 5-FU. Some intriguing structure-activity relationships were found and are discussed herein by theoretical calculation.

| S-EPMC7070458 | biostudies-literature

Poly[(?(3)-hydrogenphosphato)(4H-1,2,4-triazole-?N(1))zinc].

Project description:The asymmetric unit of the title compound, [Zn(HPO(4))(C(2)H(3)N(3))](n), contains one Zn(2+) cation, one (HPO(4))(2-) anion and a 1,2,4 triazole ligand. The Zn(2+) cation is coordinated in a quite regular tetra-hedral geometry by O atoms from three phosphate groups and a tertiary N atom from the triazole ring. Each phosphate anion is connected to three Zn(II) cations, leading to a series of corrugated organic-inorganic layers parallel to the ac plane. The overall structure involves stacking of complex hybrid organic-inorganic layers along the b axis. Cohesion in the crystal is ensured by an infinite three-dimensional network of N-H?O and O-H?O hydrogen bonds between the phosphate groups and the triazole ligands.

| S-EPMC3515161 | biostudies-literature

4-Amino-3,5-di-2-pyridyl-4H-1,2,4-triazole.

Project description:In the crystal structure of the title compound, C(12)H(10)N(6), the mol-ecules deviate slightly from planarity. The plane of the central triazole ring makes angles of 6.13 (9) and 3.28 (10)° with the pyridyl ring planes. Intra-molecular N-H⋯N inter-actions form six-membered closed rings. The crystal packing also shows weak C-H⋯π and C-H⋯N inter-actions.

| S-EPMC2960509 | biostudies-literature

4-[4-(Diethyl-amino)benzyl-ideneamino]-4H-1,2,4-triazole.

Project description:The title compound, C(13)H(17)N(5), is a Schiff base synthesized by the reaction of 4-amino-4H-1,2,4-triazole and 4-(diethyl-amino)benzaldehyde. The triazole ring forms a dihedral angle of 5.77 (16)° with the benzene ring. The crystal structure is stabilized by an inter-molecular C-H⋯N hydrogen bond.

| S-EPMC2961419 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data