2,4,6-Tri(4-pyridyl)-1,3,5-triazine - 42333-78-8

2,4,6-Tri(4-pyridyl)-1,3,5-triazine

Catalog Number: EVT-293530
CAS Number: 42333-78-8
Molecular Formula: C18H12N6
Molecular Weight: 312.3 g/mol
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Product Introduction

Description

2,4,6-Tri(4-pyridyl)-1,3,5-triazine and its derivatives are a class of compounds that have garnered significant attention in the field of medicinal and coordination chemistry due to their unique structural features and biological activities. These compounds, characterized by a triazine ring substituted with pyridyl groups, have been explored for their potential as kinase inhibitors, antifungal agents, and coordination ligands for metal complexes with various applications.

Mechanism of Action

The mechanism of action of these triazine derivatives often involves the inhibition of key enzymes or interactions with metal ions. For instance, substituted pyrrolo[2,1-f][1,2,4]triazines have been identified as potent inhibitors of tyrosine kinase activity of growth factor receptors such as VEGFR-2 and FGFR-1. These compounds competitively inhibit ATP binding, leading to the suppression of endothelial cell proliferation, which is crucial in angiogenesis and tumor growth1. Additionally, the coordination chemistry of 2,4,6-tri(pyridyl)-1,3,5-triazine ligands with metals like copper and zinc has been extensively studied. These ligands form complexes with metals, which can influence the hydrolysis of the triazine ring or contribute to the antimicrobial properties of the resulting metal complexes25.

Applications in Various Fields

Medicinal Chemistry

In medicinal chemistry, these triazine derivatives have shown promise as antifungal agents, with some compounds inhibiting strains of Candida, Aspergillus, Mucor, and Trychophyton species at low concentrations3. Furthermore, the antiproliferative activity of fluorinated triazolo[1,5-a][1,3,5]triazines against various cancer cell lines has been documented, indicating their potential as cancer therapeutics7.

Coordination Chemistry

The coordination chemistry of 2,4,6-tri(pyridyl)-1,3,5-triazine ligands is rich and varied. These ligands have been used to synthesize complexes with transition metals and lanthanides, which have applications as luminescent materials, in the preparation of coordination polymers and networks, and in the synthesis of discrete metalla-assemblies4. The structural versatility of these ligands allows for the formation of various geometries and coordination modes, which can be tailored for specific applications.

Antimicrobial Activity

Metal complexes based on 2,4,6-tri(2-pyridyl)-1,3,5-triazine ligands have been investigated for their antibacterial activity. A Zn(II) complex with this ligand exhibited significant antimicrobial effects against Gram-positive, Gram-negative bacteria, and yeast. The complex's interaction with DNA was also studied, providing insights into its mode of action5.

Properties

CAS Number

42333-78-8

Product Name

2,4,6-Tri(4-pyridyl)-1,3,5-triazine

IUPAC Name

2,4,6-tripyridin-4-yl-1,3,5-triazine

Molecular Formula

C18H12N6

Molecular Weight

312.3 g/mol

InChI

InChI=1S/C18H12N6/c1-7-19-8-2-13(1)16-22-17(14-3-9-20-10-4-14)24-18(23-16)15-5-11-21-12-6-15/h1-12H

InChI Key

CBMYFVSIIYILRH-UHFFFAOYSA-N

SMILES

C1=CN=CC=C1C2=NC(=NC(=N2)C3=CC=NC=C3)C4=CC=NC=C4

Synonyms

2,4,6-Tri-4-pyridinyl-1,3,5-triazine; 1,3,5-Tris(4-pyridyl)-2,4,6-triazine; 2,4,6-Tri(4-pyridyl)-1,3,5-triazine; 2,4,6-Tri(4-pyridyl)-s-triazine; 2,4,6-Tri(pyridin-4-yl)-1,3,5-triazine; 2,4,6-Tri-4-pyridyltriazine; 2,4,6-Tris(4-pyridinyl)-1,3,5-triaz

Canonical SMILES

C1=CN=CC=C1C2=NC(=NC(=N2)C3=CC=NC=C3)C4=CC=NC=C4

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