33893-89-9Relevant articles and documents
A green emitting phosphorescent copper(I) complex with tetrazole derived ligand for electroluminescence application
Tong, Senmiao,Yuan, Donglin,Yi, Lita
, p. 280 - 286 (2014)
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
Metal-Binding Isosteres as New Scaffolds for Metalloenzyme Inhibitors
Dick, Benjamin L.,Cohen, Seth M.
, p. 9538 - 9543 (2018)
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 photophysical investigations of novel transition metal complexes of pyridine tetrazole ligands
Malik, Rayees Ahmad,Bhat, Nawaz Gulzar,Yadav, Renu,Singh, Navjot,Kumar, Gulshan,Mal, Suraj
, p. 2159 - 2163 (2018)
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.
Two novel bipolar Ir(III) complexes based on 9-(4-(pyridin-2-yl)phenyl)-9H-carbazole and N-heterocyclic ligand
Huixia, Xu,Fang, Wang,Kexiang, Wang,Peng, Sun,Jie, Li,Tingting, Yang,Hua, Wang,Bingshe, Xu
, p. 316 - 322 (2017)
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 and structures of 5-(pyridyl)tetrazole complexes of Mn(II)
Lin, Ping,Clegg, William,Harrington, Ross W.,Henderson, Richard A.
, p. 2388 - 2394 (2005)
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.
Going from green to red electroluminescence through ancillary ligand substitution in ruthenium(ii) tetrazole benzoic acid emitters
Shahroosvand, Hashem,Najafi, Leyla,Sousaraei, Ahmad,Mohajerani, Ezeddin,Janghouri, Mohammad
, p. 6970 - 6980 (2013)
The synthesis, characterization, photoluminescence (PL) and electroluminescence (EL) properties of novel ruthenium(ii) emitters with 4-(1H-tetrazole-5-yl)benzoic acid (TzBA) as a novel basic ligand and 2,2-bipyridine (bpy), 1,10-phenanthroline (phen) and pyridine tetrazole (pyTz) as ancillary ligands have been reported. The EL results show that the luminescence of Ru(TzBA) depends on the ancillary ligands, which can be used to tune the EL color of the Ru(TzBA) complexes from green to red emission. The role of ancillary ligands in EL devices of the Ru(TzBA) complexes was investigated by DFT calculations. The device [Ru(TzBA)(bpy)(pyTz)(SCN)] (5) has a luminance of 480 cd m-2 and a maximum efficiency of 1.2 cd A-1 at 16 V, which are the highest values among the five devices studied. The turn-on voltage of this device is approximately 6 V. We suggest that an electroplex occured at the PVK-Ru complex interface when pyTz was incorporated as an ancillary ligand into Ru(TzBA). OLED studies reveal that pyTz as an ancillary ligand exhibits better current generating capacity than bpy and phen ligands, which are introduced by an emitter (5).
Synthesis of novel tetrazole transition metal complexes for advanced photonic applications
Malik, Rayees Ahmad,Bhat, Nawaz Gulzar,Yadav, Renu,Singh, Navjot,Kumar, Gulshan,Mal, Suraj
, p. 520 - 524 (2018)
As tetrazole themselves revealed a rich photochemistry and are piquantly affected by the presence of substituents on tetrazole ring. This exertion explores the harmony of two bidentate ligands-pyridine tetrazole (Hpytz) and pyridine tetrazole-N-oxide (Hpytzo) as "antennae" and their complexes with transition metals (Fe3+, Co2+, Ni2+, Zn2+ and Ru3+). The erections of these pyridine tetrazole metal complexes were elucidated by UV, IR and 1H NMR by using DMSO, acetonitrile as solvents in which these metal complexes persist in undissociated form and also show high melting point >360 °C. These pyridine tetrazole ligands ("antennae") sensitize efficiently the metal centre and stimulus the absorption window of pyridine tetrazole transition metal complexes, which was appreciably stretched towards the UV-visible region of 400-800 nm. The wavelength of these ligands λemission was found to be amplified upto 522-540 nm (λexcitation = 270 nm) that might enlightens the extremely conjugated unsaturated system which triggers the UV-region and for metal complexes (λexcitation, Fe3+ = 270 nm, Co2+ = 280 nm, Ni2+ = 285 nm, Zn2+ = 270 nm and Ru3+ = 260 nm (λemission, Fe3+ = 522.5 nm, Co2+ = 576 nm, Ni2+ = 554 nm, Zn2+ = 521 nm and Ru3+ = 522 nm). The escalation in λemission of the metal complexes with novel designed tetrazole ligands spectacles a drift on complex formation due to the augmented conjugation and conformation, which might sensitizes luminescence properties as reported with La(III) complexes more proficiently. The fluorescent property revealed with these neutral pyridine tetrazole derivatives stipulate an efficient alternative to that of usual dipicolinate analogues.
Selective Synthesis and Complexation of Novel N,N′-Alkylene-Bridged Bis(5-pyridyltetrazole)
Voitekhovich, Sergei V.,Mosalkova, Anastasiya P.,Lyakhov, Alexander S.,Ivashkevich, Ludmila S.,Schmorl, Sara,Kersting, Berthold,Ivashkevich, Oleg A.
, p. 1611 - 1617 (2018)
A novel N,N′-alkylene-bridged bis(5-pyridyltetrazole) ligand, namely 2,5-bis[5-(2-pyridyl)-tetrazol-2-yl]-2,5-dimethylhexane (bpt), was prepared by regioselective N2-alkylation of 5-(2-pyridyl)tetrazole with 2,5-dimethylhexane-2,5-diol in perchloric acid. The ligand bpt was found to react with copper(II) chloride to give the dinuclear complex [Cu2(bpt)Cl4]. According to single-crystal X-ray analysis of the complex, bpt acts as a chelating ligand, coordinated by the metal through the tetrazole ring N4 and the pyridine ring nitrogen atoms. In the complex molecule, two copper atoms are linked by double chlorido bridges, and ligand bpt plays the role of the third bridge. The temperature-dependent magnetic susceptibility measurements of the complex revealed that the copper(II) ions were weakly antiferromagnetically coupled showing a coupling constant J of –1.04 cm–1.
A Ratiometric Tetrazolylpyridine-Based "turn-On" Fluorescent Chemosensor for Zinc(II) Ion in Aqueous Media
Kaleeswaran, Palanichamy,Azath, Ismail Abulkalam,Tharmaraj, Vairaperumal,Pitchumani, Kasi
, p. 1361 - 1366 (2014)
The highly selective ratiometric "turn-on" fluorescent sensing of Zn2+ ion involving 2-(1H-tetrazole-5-yl)pyridine (2PT) in aqueous medium is reported, which is not observed when other metal ions are present. Upon 2PT binding selectively with Zn2+ ion, a fluorescence enhancement is observed that is attributed to an enhancement of localized emission and suppression of excited-state intramolecular proton transfer. The described sensing system involving 2PT is also successfully applied to the detection of Zn2+ ion in real samples with a detection limit of 7.5×10-7 M.
CuO–NiO bimetallic nanoparticles supported on graphitic carbon nitride with enhanced catalytic performance for the synthesis of 1,2,3-triazoles, bis-1,2,3-triazoles, and tetrazoles in parts per million level
Gajurel, Sushmita,Dam, Binoyargha,Bhushan, Mayank,Singh, L. Robindro,Pal, Amarta Kumar
, (2021/12/09)
The unification of CuCl2·2H2O and NiCl2·6H2O with the support of graphitic carbon nitride yielded to form an efficient, synergistic, bimetallic nano-catalyst CuO–NiO@g-C3N4. FT-IR, SEM, TEM
Catalytic conversion of 2,4,5-trisubstituted imidazole and 5-substituted 1H-tetrazole derivatives using a new series of half-sandwich (η6-p-cymene)Ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazone ligands
Vinoth, Govindasamy,Indira, Sekar,Bharathi, Madheswaran,Archana, Govindhasamy,Alves, Luis G.,Martins, Ana M.,Shanmuga Bharathi, Kuppannan
, (2020/11/16)
A new series of half-sandwich (η6-p-cymene) ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazide derivatives [Ru(η6-p-cymene)(Cl)(L)] [L = N'-(naphthalen-1-ylmethylene)thiophene-2-carbohydrazide (L1), N'-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide (L2) and N'-(pyren-1-ylmethylene)thiophene-2-carbohydrazide (L3)] were synthesized. The ligand precursors and their Ru(II) complexes (1–3) were structurally characterized by spectral (IR, UV–Vis, NMR and mass spectrometry) and elemental analysis. The molecular structures of the ruthenium(II) complexes 1–3 were determined by single-crystal X-ray diffraction. All complexes were used as catalysts for the one-pot three-component syntheses of 2,4,5-trisubstitued imidazole and 5-substituted 1H-tetrazole derivatives. The catalytic studies optimized parameters as solvent, temperature and catalyst. The catalysts revealed very active for a broad range of aromatic aldehydes presenting either electron attractor or electron donor substituents and, although less active, moderate to high activities were observed for alkyl aldehydes.
Fe3O4@L-lysine-Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles
Ashraf, Muhammad Aqeel,Liu, Zhenling,Li, Cheng,Zhang, Dangquan
, (2020/12/23)
An efficient and sustainable synthetic protocol has been presented to synthesis and 5-substituted 1H-tetrazole privileged heterocyclic substructures. The synthetic protocol involves two-component reaction between aryl nitriles and NaN3 in water using complex of L-lysine-palladium nanoparticles (NPs) modified Fe3O4 nanoparticles as magnetically separable, recyclable, and reusable heterogeneous catalyst. Magnetically retrievable L-lysine-Pd(0) modified Fe3O4 nanoparticles were applied in [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles. The advantages of this strategy include easy recovery and efficient reusability of the expensive Pd NPs, obtaining high yields of [2 + 3] cycloaddition, short reaction times, and all of the reported synthetic strategies are being performed in water as green solvent for a wide range of substrates.
