33893-89-9

Usage

Uses

Used in Pharmaceutical Industry:
4-(2H-TETRAZOL-5-YL)-PYRIDINE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential applications in treating different diseases.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-(2H-TETRAZOL-5-YL)-PYRIDINE is used as a building block for creating complex organic molecules. Its reactivity and structural diversity make it a valuable component in the design and synthesis of novel chemical entities.
Used in Coordination Chemistry:
4-(2H-TETRAZOL-5-YL)-PYRIDINE is used as a ligand in coordination chemistry, forming stable complexes with metal ions. This application is particularly relevant in the synthesis and crystal structure of metal complexes, such as the [Ag(2-allyl-5-phenyl-2Htetrazole)ClO4] π,?-complex mentioned in the provided materials. These complexes have potential applications in various fields, including catalysis, materials science, and medicinal chemistry.

InChI:InChI=1/C6H4N5/c1-2-4-7-5(3-1)6-8-10-11-9-6/h1-4H/q-1

Upstream product

• 100-70-9 2-Cyanopyridine 
• 1005-02-3 pyridine-2-carboxamidrazone 
• 7647-01-0 hydrogenchloride 
• 68-12-2 N,N-dimethyl-formamide 
• 1121-60-4 pyridine-2-carbaldehyde 
• 109-06-8 α-picoline 
• 586-98-1 2-Hydroxymethylpyridine 
• 197958-29-5 pyridin-2-ylboronic acid 
• 5346-38-3 pyridine-2-carbothioamide 
• 109-04-6 2-bromo-pyridine 

Downstream Products

• 81186-94-9 mesitylenesulfonyl 5-(pyridin-2-yl) tetrazolide 
• 81186-95-0 2,4,6-triisopropylbenzenesulfonyl 5-(pyridin-2-yl) tetrazolide 
• 171018-17-0 2-(2-methyl-2H-tetrazol-5-yl)pyridine 
• 171018-16-9 2-(1-methyl-1H-tetrazol-5-yl)pyridine 
• 25433-30-1 2-(4-dimethylamino-penyl)-5-(2-pyridinyl)-1,3,4-oxadiazole 
• 63279-76-5 N-phenyl-5-(pyridin-2-yl)-1,3,4-thiadiazole-2-amine 
• 60838-23-5 N-phenyl-(5-pyridin-2-yl)[1,3,4]oxadiazole-2-yl-amine 
• 828-51-3 1-Adamantanecarboxylic acid 
• 1415251-74-9 C₁₇H₁₉N₃O 
• 1415251-75-0 C₁₆H₁₅N₃O 
• 1415251-76-1 C₁₉H₁₄N₄O 
• 1445903-73-0 [Cu(9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene)(5-(2-pyridyl)-tetrazolate)] 
• 1416587-30-8 [Cu(triphenylphosphine)₂(5-(2-pyridyl)-tetrazolate)] 
• 132766-74-6 2-(5-(pyridin-2-yl)-2H-tetrazole-2-yl)acetic acid 

Relevant academic research and scientific papers

A green emitting phosphorescent copper(I) complex with tetrazole derived ligand for electroluminescence application

In this paper, a tetrazole derived diamine ligand of 2-(1H-tetrazol-5-yl) pyridine (TP) owing electron-donors and short conjugation chain was synthesized to increase the band gap of its corresponding phosphorescent Cu(I) complex. This Cu(I) complex was ch

Thiocyanate-free ruthenium(II) sensitizer with a pyrid-2-yltetrazolate ligand for dye-sensitized solar cells

The synthesis of the new complex [Ru(Tetrazpy)(dcbpy)2]Cl is reported, along with its spectroscopical, electrochemical, and theoretical characterization. The first dye-sensitized solar cell device with this complex has been prepared, leading to a 3% of conversion efficiency, promising data considering the simplicity of the Tetrazpy ligand.

Metal-Binding Isosteres as New Scaffolds for Metalloenzyme Inhibitors

The principle of isosteres or bioisosteres in medicinal chemistry is a central and essential concept in modern drug discovery. For example, carboxylic acids are often replaced by bioisosteres to mitigate issues related to lipophilicity or acidity while retaining acidic characteristics in addition to hydrogen bond donor/acceptor abilities. Separately, the development of metal-binding pharmacophores (MBPs) for binding to the active site metal ion in metalloenzymes of therapeutic interest is an emerging area in the realm of fragment-based drug discovery (FBDD). The direct application of the bioisostere concept to MBPs has not been well-described or systematically investigated. Herein, the picolinic acid MBP is used as a case study for the development of MBP isosteres (so-called MBIs). Many of these isosteres are novel compounds, and data on their physicochemical properties, metal binding capacity, and metalloenzyme inhibition characteristics are presented. The results show that MBIs of picolinic acid generally retain metal coordinating properties and exhibit predictable metalloenzyme inhibitory activity while possessing a broad range of physicochemical properties (e.g., pKa, logP). These findings demonstrate the use of bioisosteres results in an untapped source of metal binding functional groups suitable for metalloenzyme FBDD. These MBIs provide a previously unexplored route for modulating the physicochemical properties of metalloenzyme inhibitors and improving their drug-likeness.

Synthesis and Characterization of New Phosphorescent Heteroleptic Iridium (III) Complex by Using Tetrazole as an Ancillary Ligand for Organic Light-Emitting Diodes

The yellow emitting tetrazole based heteroleptic iridium(III) complex, bis(diphenylquinoline)iridium(pyridyltetrazole)[(DPQ)2Ir(PyTz)], was synthesized and conformed by 1H-,13C NMR spectral techniques. The purity was also

Synthesis and photophysical investigations of novel transition metal complexes of pyridine tetrazole ligands

Two bidentate pyridine-tetrazole ligands viz. pyridine tetrazole (Hpytz) and pyridine tetrazole-N-oxide (Hpytzo), which are integrated in vitro from pyridine carbonitrile by thermal cycloaddition reaction with sodium azide for complexation with transition metals (Fe3+, Co2+, Ni2+, Zn2+ and Ru3+) to improve sophisticated photonic appliances in them as perceived in Ln (III) complexes. The configuration investigation of bis and tris-complexes was studied in solution by UV, FTIR and1H NMR techniques. The hetero-nuclear pyridine tetrazole metal complexes display a close performance concerning the photo-physical properties as displayed by lanthanide(III) complexes and conventional carboxylate analogous.

Design, Synthesis, Single X-Ray Crystal Structure, DFT and Molecular Docking Studies of Novel Clip Type-Pyridyltetrazole Analogues

Novel clip type-pyridyltetrazole analogs of 1,3-bis(5-(pyridin-2-yl)-1H-tetrazol-1-yl)propan-2-ol (3A) and 1,3-bis(5-(pyridin-2-yl)-2H-tetrazol-2-yl) propan-2-ol (3B) have been synthesized by the reaction of 2-(1H-tetrazol-5-yl)pyridine (2) with 0.5 equivalent of epichlorohydrine in DMF using K2CO3 as a base. Relevant monomers of 1-chloro-3-(5-(pyridin-2-yl)-1H-tetrazol-1-yl)propan-2-ol (3C) and 1-chloro-3-(5-(pyridin-2-yl)-2H-tetrazol-2-yl)propan-2-ol (3D) have been synthesized by reaction of compound 2 with one equivalent of epichlorohydrine in DMF using K2CO3 as a base. The compounds 3C and 3D are further modified by the reaction sequences to obtain the ligands 1-(2-(hydroxymethyl)phenoxy)-3-(5-(pyridin-2-yl)-1H-tetrazol-1-yl)propan-2-ol (3G) and 1-(2-(hydroxymethyl)phenoxy)-3-(5-(pyridin-2-yl)-2H-tetrazol-2-yl)propan-2-ol (3H) respectively. The eight synthesized compounds (3A-3H) were characterized by 1H NMR, 13C NMR, IR and Mass spectroscopy. The compound 3A, was crystallized in triclinic primitive system space group P2(1)/c with a = 8.9442 ?, b = 9.2097 ?, c = 11.3558 ?, V = 814.68 ?, R1 = 0.0213 at 298 K. The compounds 3A and 3B were optimized, HOMO/ LUMO and molecular electrostatic potential studies were carried by DFT calculations with B3LYP/6.311G** method. The molecular docking studies were performed on 3A, 3B, 3G and 3H and the studies reveal that all the compounds exist in crescent shapes.

Two novel bipolar Ir(III) complexes based on 9-(4-(pyridin-2-yl)phenyl)-9H-carbazole and N-heterocyclic ligand

Two novel bipolar Ir(III) complexes named (Czppy)2Ir(tfmptz) and (Czppy)2Ir(pptz) were synthesized and characterized, where the Czppy is 9-(4-(pyridin-2-yl)phenyl)-9H-carbazole, tfmptz refers to 2-(3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl)pyridine and Hpptz represents 2-(1H-tetrazol-5-yl)pyridine, respectively. Their molecular structures were confirmed by 1H NMR and photophysical were investigated. The performances in phosphorescent organic light emitting devices (PhOLEDs) were characterized by a heavy doping concentration of 20 wt% in host as emitting layer. The results suggest that the number of nitrogen atoms in ancillary has no obvious effects on their photophysical properties. Both (Czppy)2Ir(tfmptz) and (Czppy)2Ir(pptz) display the blue-green emission with the peaks at 492, 526 nm. The performances of complexes (Czppy)2Ir(tfmptz) in PhOLEDs superior to that of the (Czppy)2Ir(pptz) due to the poor thermal stability.

Synthesis, Characterization, and Biological Activities of Pendant Arm-Pyridyltetrazole Copper(II) Complexes: DNA Binding/Cleavage Activity and Cytotoxic Studies

2-(1H-Tetrazol-5-yl)pyridine (L) has been reacted separately with Me2NCH2CH2Cl·HCl and ClCH2CH2OH to yield two regioisomers in each case, N,N-dimethyl-2-[5-(pyridin-2-yl)-1H-tetrazol-1-yl]ethanamine (L1)/N,N-dimethyl-2-[5-(pyridin-2-yl)-2H-tetrazol-2-yl]ethanamine (L2) and 2-[5-(pyridin-2-yl)-1H-tetrazol-1-yl]ethanol (L3)/2-[5-(pyridin-2-yl)-2H-tetrazol-2-yl]ethanol (L4), respectively. These ligands, L1-L4, have been coordinated with CuCl2·H2O in 1:1 composition to furnish the corresponding complexes 1-4. EPR Spectra of Cu complexes 1 and 3 were characteristic of square planar geometry, with nuclear hyperfine spin 3/2. Single X-ray crystallographic studies of 3 revealed that the Cu center has a square planar structure. DNA binding studies were carried out by UV/VIS absorption; viscosity and thermal denaturation studies revealed that each of these complexes are avid binders of calf thymus DNA. Investigation of nucleolytic cleavage activities of the complexes was carried out on double-stranded pBR322 circular plasmid DNA by using a gel electrophoresis experiment under various conditions, where cleavage of DNA takes place by oxidative free-radical mechanism (OH·). In vitro anticancer activities of the complexes against MCF-7 (human breast adenocarcinoma) cells revealed that the complexes inhibit the growth of cancer cells. The IC50 values of the complexes showed that Cu complexes exhibit comparable cytotoxic activities compared to the standard drug cisplatin.

Synthesis and structures of 5-(pyridyl)tetrazole complexes of Mn(II)

New MnII complexes containing 5-(2-pyridyl)tetrazole, 5-(3-cyano-4-pyridyl)tetrazole or 5-(4-pyridyl)tetrazole ligands are described. The complexes are prepared by reaction of the corresponding cyanopyridines with sodium azide in the presence of MnII salts. All the complexes have been characterized by X-ray crystallography, which reveals that 5-(pyridyl)tetrazole ligands can coordinate to Mn through either type of nitrogen atom in the tetrazole residue or via the pyridyl group. In the solid state, extended 2D and 3D structures are produced through networks of hydrogen bonding (involving water molecules and the tetrazolate residue). Acidification of the complexes produces the corresponding free 5-(pyridyl)-1H-tetrazole. The Royal Society of Chemistry 2005.

Strongly photoluminescent Eu(III) tetrazolate ternary complexes with phosphine oxides as powerful sensitizers

The Eu(III) cation forms electrically neutral photoluminescent complex with 5-(2-pyridyl-1-oxide)tetrazolate (PTO) anion. Although the photoluminescence properties of such tertiary Eu(III) and Tb(III) complexes were not as high (13 and 31% photoluminescence quantum yield, respectively) as reported for other diketonate lanthanide complexes probably because of high number of nitrogen atoms involved in PTO which leads to attachment of water molecules, reducing the luminescence quantum yield with vibrational and rotational quenching. Here, we report the removal of quencher molecules from the coordination sphere of tris-europium tetrazolate oxide complex by replacing them with various phosphine oxides which leads to improved photoluminescence quantum yield for the complexes by acting as auxiliary co-ligands with that of the main antenna 5-(2-pyridyl-1-oxide)tetrazolate. The coordination sphere in these complexes can be complemented by aromatic phosphine oxides to provide highly photoluminescent Eu(III) complexes. The highest quantum yield was 38% in 3 [Eu(PTO)3·DPEPO](H2O)5 containing bis(2-(diphenylphosphino)phenyl) ether oxide (DPEPO) as compared to tris-europium complex with 5-(2-pyridyl-1-oxide)tetrazolate.