- Design and Synthesis of a BODIPY-Tetrazole Based “Off-On” in-Cell Fluorescence Reporter of Hydrogen Peroxide
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BODIPY-linked bithiophene-tetrazoles were designed and synthesized for bioorthogonal photoclick reactions in vitro and in vivo. The reactivity of these tetrazoles toward dimethyl fumarate was found to depend on the BODIPY attachment site, with the meta-linked BODIPY–tetrazole being the most reactive. The resulting pyrazoline cycloadduct showed drastically reduced BODIPY fluorescence. However, BODIPY fluorescence recovered after treatment with hydrogen peroxide. This turn-on effect was attributed to conversion from the pyrazoline to a pyrazole. Finally, we showed that this unique BODIPY–tetrazole off–on fluorescence probe can be used to detect hydrogen peroxide inside HeLa cells.
- An, Peng,Lewandowski, Tracey M.,Lin, Qing
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- Highly active and reusable cu/c catalyst for synthesis of 5-substituted 1h-tetrazoles starting from aromatic aldehydes
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A new, efficient and convenient method for the synthesis of 5-substituted 1H-tetrazole derivatives with a wide range of substituents in good to excellent yields has been developed. The synthesis was performed by the one-pot three-component [3+2]cycloaddit
- Khalifeh, Reza,Khalili, Dariush,Rastegar, Najme
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p. 1044 - 1052
(2021/06/07)
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- One-Pot Suzuki-Hydrogenolysis Protocol for the Modular Synthesis of 2,5-Diaryltetrazoles
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2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the prac
- Bertrand, Sophie,Jamieson, Craig,Livingstone, Keith
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p. 7413 - 7423
(2020/07/07)
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- A robust and recyclable ionic liquid-supported copper(II) catalyst for the synthesis of 5-substituted-1H-tetrazoles using microwave irradiation
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Abstract: A novel and robust ionic liquid-supported copper(II) catalyst has been developed and explored for the efficient synthesis of 5-substituted-1H-tetrazoles using microwave irradiation. The ionic liquid-supported catalyst facilitated the efficient isolation of tetrazole products with high purity by simple extraction with organic solvent. Recovered ionic liquid-supported copper(II) catalyst could be recycled for three times for the synthesis of tetrazole products with high purity. This synthetic protocol offers a very clean, convenient, and microwave-assisted environment-friendly method for the efficient synthesis of 5-substituted-1H-tetrazoles with high yield. Graphic abstract: [Figure not available: see fulltext.].
- Padmaja,Chanda, Kaushik
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p. 1307 - 1317
(2019/11/14)
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- HETEROCYCLIC COMPOUNDS AS FUNGICIDES
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The present invention relates to novel heterocyclic compound of Formula (I), (I) wherein, Het, L1, A, L2 and R12 are as defined in the detailed description, for use as fungicides.
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- Tetrazolylpropan-2-ones as inhibitors of fatty acid amide hydrolase: Studies on structure-activity relationships and metabolic stability
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A series of derivatives of 1-(4-octylphenoxy)-3-(2H-tetrazol-2-yl)propan-2-one (3) and 1-(4-octylphenoxy)-3-(1H-tetrazol-1-yl)propan-2-one (4) was synthesized and tested for fatty acid amide hydrolase (FAAH) inhibitory potency and phase I metabolic stability. Introduction of certain substituents like 4-chlorophenyl, 4-methoxycarbonylphenyl and carboxyl in position 5 of the tetrazole ring of 3 led to a significant increase of the metabolic stability of the scissile ketone pharmacophore, while the high activity towards FAAH was not affected markedly. In contrast, substituents in position 5 of the heterocyclic system of 4 did not have a considerable impact on the undesired ketone reduction. Furthermore, the effect of shielding the ketone group of some derivatives of 3 by a methyl substituent in position 3 of the propan-2-one scaffold and the consequences of the replacement of the lipophilic octyl residue of these compounds by more drug-like substituents were examined.
- Garzinsky, David,Zahov, Stefan,Ekodo Voundi, Merlin,Hanekamp, Walburga,Lehr, Matthias
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supporting information
p. 183 - 192
(2018/10/21)
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- A Practical Synthesis of 5-Substituted 1 H -Tetrazoles from Aldoximes Employing the Azide Anion from Diphenyl Phosphorazidate
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5-Substituted 1 H -tetrazoles were effectively synthesized from aldoximes and diphenyl phosphorazidate (DPPA) under reflux conditions in xylenes. Various aldoximes underwent the cycloaddition reaction to afford the corresponding 5-substituted 1 H -tetrazoles in short reaction times and in good yields. Chiral aldoximes derived from amino acids also gave aminotetrazoles with almost no racemization.
- Ishihara, Kotaro,Kawashima, Mayumi,Matsumoto, Takatoshi,Shioiri, Takayuki,Matsugi, Masato
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p. 1293 - 1300
(2017/12/26)
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- [Cu(phen)(PPh3)2]NO3-catalyzed microwave-assisted green synthesis of 5-substituted 1H-tetrazoles
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Abstract: An efficient synthetic methodology for construction of 5-substituted 1H-tetrazoles under microwave irradiation in green medium is described. With [Cu(phen)(PPh3)2]NO3 as catalyst and H2O-isopropyl alcohol (IPA) as reaction medium, various substituted nitriles underwent (3?+?2) cycloaddition reaction with NaN3 under microwave irradiation to provide corresponding 5-substituted 1H-tetrazoles in high yield. This method is not only efficient and general but also benefits from high functional group tolerance. This environmentally friendly synthetic methodology is visualized as an alternative to existing procedures, providing a simple route to privileged scaffolds.
- Padmaja,Meena,Maiti, Barnali,Chanda, Kaushik
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p. 7365 - 7374
(2017/09/06)
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- Synthesis of 5-Substituted 1 H -Tetrazoles from Aldoximes Using Diphenyl Phosphorazidate
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A novel method for the synthesis of 5-substituted 1H-tetrazoles using diphenyl phosphorazidate (DPPA) has been developed. Aromatic and aliphatic aldoximes underwent cycloaddition to afford the corresponding 5-substituted 1H-tetrazoles with ease and efficiency.
- Ishihara, Kotaro,Kawashima, Mayumi,Shioiri, Takayuki,Matsugi, Masato
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supporting information
p. 2225 - 2228
(2016/11/06)
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- Preparation of 5-substituted 1H-tetrazoles catalyzed by scandium triflate in water
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Several 5-substituted 1H-tetrazoles were prepared in water or isopropanol/water mixtures using microwave heating. Good yields were obtained for the [2 + 3] cycloaddition of sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles when catal
- Coca, Adiel,Turek, Evan,Feinn, Liana
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p. 218 - 225
(2015/11/02)
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- Microwave Synthesis of 5-Substituted 1 H-Tetrazoles Catalyzed by Bismuth Chloride in Water
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(Chemical Equation Presented). Bismuth chloride was used to catalyze the [2 + 3] cycloaddition between sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles. A number of 5-substituted 1H-tetrazoles were synthesized in water or isopropano
- Coca, Adiel,Feinn, Liana,Dudley, Joshua
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p. 1023 - 1030
(2015/03/30)
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- CuFe2O4 nanoparticle mediated method for the synthesis of 5-substituted 1H-tetrazoles from (E)-aldoximes
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A strategy for the synthesis of 5-substituted 1H-tetrazoles from various (E)-aldoximes and sodium azide was adopted using copper ferrite nanoparticles as a reusable catalyst.
- Akula, Ravi Kumar,Adimulam, Chandra S.,Gangaram, Sathaiah,Kengiri, Raju,Banda, Narsaiah,Pamulaparthy, Shanthan R.
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p. 440 - 445
(2014/05/20)
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- Going from green to red electroluminescence through ancillary ligand substitution in ruthenium(ii) tetrazole benzoic acid emitters
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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).
- Shahroosvand, Hashem,Najafi, Leyla,Sousaraei, Ahmad,Mohajerani, Ezeddin,Janghouri, Mohammad
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p. 6970 - 6980
(2013/10/22)
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- The synthesis of 5-substituted 1H-tetrazoles in molten tetrabutylammonium bromide
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An economical and environmentally benign method for the synthesis of 5-substituted 1H-tetrazoles has been established. In this protocol, molten tetrabutylammonium bromide (TBAB) is used as both the solvent and catalyst. A mechanism involving the intermedi
- Xie, Aming,Cao, Meiping,Feng, Liandong,Dong, Wei
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p. 665 - 667
(2014/01/17)
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- Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction
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The design and synthesis of a new class of laser light activatable tetrazoles with extended π-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M-1 s-1. The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.
- An, Peng,Yu, Zhipeng,Lin, Qing
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supporting information
p. 5496 - 5499
(2013/11/19)
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- FUSED HETEROCYCLIC COMPOUNDS AND THROMBOPOIETIN RECEPTOR ACTIVATORS
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Fused heterocyclic compounds useful for prevention, treatment or improvement of diseases against which activation of the thrombopoietin receptor is effective are provided. A compound represented by the formula (I) (wherein R1 is an aryl group fused to a saturated ring or the like, A, B, L1, R2, L2, L3, Y, L4, R3 and X are defined in the description), a tautomer, prodrug or a pharmaceutically acceptable salt of the compound or a solvate thereof.
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Page/Page column 35
(2012/08/28)
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- Assembly of super-supertetrahedral metal-organic clusters into a hierarchical porous cubic framework
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A porous framework comprising a super-supertetrahedral metal-organic cluster building block has been synthesized. Its cubic framework represents a multi-level hierarchical architecture and also possesses an interesting magnetic property.
- Wang, Le,Morales, Jason,Wu, Tao,Zhao, Xiang,Beyermann, Ward P.,Bu, Xianhui,Feng, Pingyun
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supporting information; experimental part
p. 7498 - 7500
(2012/10/18)
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- A simple, advantageous synthesis of 5-substituted 1 h -tetrazoles
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An advantageous synthesis of 5-substituted 1H-tetrazoles has been developed by treatment of organic nitriles with NaN3 in the presence of iodine or the heterogeneous catalyst, silica-supported sodium hydrogen sulfate (NaHSO4SiO2). Georg Thieme Verlag Stuttgart New York.
- Das, Biswanath,Reddy, Cheruku Ravindra,Kumar, Duddukuri Nandan,Krishnaiah, Martha,Narender, Ravirala
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experimental part
p. 391 - 394
(2010/04/24)
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- Tetrazoles: A new class of compound for crystallization modification
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Tetrazoles are a class of organic compound often used as carboxylic acid analogues. This analogous behaviour is shown to extend to crystallization modification, that is, tetrazoles are also able to influence crystal growth and morphology although in a dif
- Massi, Massimiliano,Ogden, Mark I.,Radomirovic, Tomoko,Jones, Franca
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body text
p. 4205 - 4207
(2011/07/08)
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- Synthesis of a novel β-diketone containing carbazole and 2,5-diphenyl-1,3,4-oxadiazole fragments
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A novel β-diketone containing carbazole and 2,5-diphenyl-1,3,4- oxadiazole fragments as hole- and electron-transporting functional groups, respectively, was synthesized via efficient and convenient procedure. The product attracts interest from the viewpoint of its potential applications as optoelectronic material.
- Tang, Huaijun,Zhang, Zhiguo,Cong, Changjie,Zhang, Keli
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experimental part
p. 559 - 563
(2009/09/06)
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- MODULATORS OF ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTORS AND THERAPEUTIC USES THEREOF
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The present invention relates to compounds with α7 nAChR agonistic activity, processes for their preparation, pharmaceutical compositions containing the same and the use thereof for the treatment of neurological, psychiatric, cognitive, immunological and inflammatory disorders.
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Page/Page column 24-25
(2010/02/15)
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- 5-Aryltetrazole Compounds, compositions thereof, and uses therefor
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The present invention relates to 5-Aryltetrazole compounds, compositions comprising a 5-Aryltetrazole compound, and methods for treating an inflammation disease, a reperfusion disease, hyperuricemia, gout, or tumor-lysis syndrome in an animal in need ther
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