13616-37-0

Usage

Uses

Used in Chemical Synthesis:
ETHYL 2-(2H-1,2,3,4-TETRAAZOL-5-YL)ACETATE is used as a starting reagent for the synthesis of ethyl aryloxadiazolylacetates. Its unique tetrazole structure makes it a valuable component in the creation of these compounds, which can have various applications in different industries.
Used in Pharmaceutical Applications:
ETHYL 2-(2H-1,2,3,4-TETRAAZOL-5-YL)ACETATE is used as a key component in the preparation of homochiral 3D diamondoid metal-organic frameworks, such as [Zn2(etza)4]. These frameworks have potential applications in drug delivery, catalysis, and other areas of pharmaceutical research.
Used in Enzyme Research:
ETHYL 2-(2H-1,2,3,4-TETRAAZOL-5-YL)ACETATE has been reported to have an effect on the glutaminyl cyclase activity of the recombinant human glutaminyl cyclase (QC). This makes it a valuable tool in the study of enzyme function and the development of new therapeutic strategies.

InChI:InChI=1/C5H8N4O2/c1-2-11-5(10)3-4-6-8-9-7-4/h2-3H2,1H3,(H,6,7,8,9)

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 123-91-1 1,4-dioxane 

Downstream Products

• 88669-78-7 (2-Benzyloxymethyl-2H-tetrazol-5-yl)-acetic acid ethyl ester 
• 88669-73-2 (1-Benzyloxymethyl-1H-tetrazol-5-yl)-acetic acid ethyl ester 
• 88669-77-6 ethyl (2-benzyl-2H-tetrazol-5-yl)acetate 
• 88669-72-1 ethyl (1-benzyl-1H-tetrazol-5-yl)acetate 
• 91660-69-4 ethyl 3-(dimethylamino)-2-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]-2-propenoate 
• 91660-68-3 (E)-3-Dimethylamino-2-[1-(4-methoxy-benzyl)-1H-tetrazol-5-yl]-acrylic acid ethyl ester 
• 91660-72-9 ethyl 2-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]acetate 
• 91660-71-8 ethyl 2-(5-(4-methoxybenzyl)tetrazolyl)acetate 
• 89488-96-0 ethyl (2-methyl-2H-tetrazol-5-yl)acetate 
• 5250-25-9 ethyl 2-(1-methyl-1H-tetrazol-5-yl)acetate 
• 5932-27-4 ethyl 1H-pyrazole-3-carboxylate 
• 4882-92-2 ethyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)acetate 
• 186368-61-6 ethyl (5-(4-methoxyphenyl)-[1,3,4]oxadiazol-2-yl)acetate 
• 70786-25-3 (tetrazolo-5-yl)acetanilide 

Relevant academic research and scientific papers

Heteropolyacid catalyzed click synthesis of 5-substituted 1H-tetrazoles from [bmim]N3 and nitriles under solvent-free conditions

A simple and solvent-free route for the synthesis of 5-substituted 1H-tetrazoles is reported. In this method, 5-substituted 1H-tetrazoles are synthesized from nitriles and [bmim]N3 with heteropolyacid (H 3PW12O40/sub

Challenging the Limits of Nitro Groups Associated with a Tetrazole Ring

To challenge the limits of nitro groups associated with a tetrazole ring, the polynitrotetrazoles, 2,5-bis(dinitromethyl)-2H-tetrazole, and 2-(dinitromethyl)-5-(trinitromethyl)-2H-tetrazole as well as their salts, were designed, synthesized, and characterized. The neutral compounds were also studied by natural bonding orbital (NBO) and Hirshfeld surface calculations. The heats of formation were calculated with Gaussian 03 and combined with experimentally determined densities in order to obtain the detonation properties of the energetic materials with the EXPLO5 program. They exhibit high densities, good oxygen balances, positive heats of formation, and excellent detonation properties.

Energetic high-nitrogen compounds: 5-(trinitromethyl)-2 H -tetrazole and -tetrazolates, preparation, characterization, and conversion into 5-(dinitromethyl)tetrazoles

A convenient access to 5-(trinitromethyl)-2H-tetrazole (HTNTz) has been developed, based on the exhaustive nitration of 1H-tetrazole-5-acetic acid, which was prepared from ethyl cyanoacetate and HN3 in a 1,3-dipolar cycloaddition reaction, followed by basic hydrolysis. HTNTz was converted into the ammonium, guanidinium, rubidium, cesium, copper, and silver 5-(trinitromethyl)-2H-tetrazolates. In addition, the ammonia adducts of the copper and silver salts were isolated. The reaction of HTNTz with hydrazine and hydroxylamine resulted in the formation of hydrazinium 5-(dinitromethyl) tetrazolate and hydroxylammonium 5-(dinitromethyl)-1H-tetrazolate, respectively. Acid treatment of both 5-(dinitromethyl)tetrazolates resulted in the isolation of 5-(dinitromethylene)-4,5-dihydro-1H-tetrazole, which was converted into potassium 5-(dinitromethyl)-1H-tetrazolate by reaction with K2CO 3. All prepared compounds were fully characterized by 1H, 13C, 14N, and 15N NMR spectroscopy and X-ray crystal structure determination. Initial safety testing (impact, friction, and electrostatic sensitivity) and thermal stability measurements (differential thermal analysis, DTA) were also carried out. The 5-(trinitromethyl) and 5-(dinitromethyl)tetrazoles are highly energetic materials that explode upon impact or heating.

Computer design, synthesis, and bioactivity analyses of drugs like fingolimod used in the treatment of multiple sclerosis

Multiple sclerosis (MS) is a very common disease of vital importance. In the MS treatment, some drugs such as fingolimod which help to protect nerves from damage are used. The main goal of the drug therapy in MS is to take control of the inflammation whic

Magnetization of biochar nanoparticles as a novel support for fabrication of organo nickel as a selective, reusable and magnetic nanocatalyst in organic reactions

Catalyst species are an important class of materials in chemistry, industry, medicine and biotechnology. Also, waste recycling is an important process in green chemistry and economic efficiency. Therefore, in order to recycle waste, biochar nanoparticles were prepared from chicken manure. Then, the biochar nanoparticles were magnetized under a green and environmentally friendly method. Finally, the surface of the magnetic biochar nanoparticles was modified and further they were applied as a novel support for fabrication of nickel as a homoselective and reusable catalyst in organic reactions. The structure of this organic-inorganic catalyst has been characterized by N2adsorption-desorption isotherms, and the SEM, EDS, WDX, XRD, TGA, AAS, FT-IR and VSM techniques. This magnetically recyclable catalyst was used in the homoselective synthesis of tetrazole and pyranopyrazole derivatives. This catalyst can be reused several times without significant loss of its catalytic efficiency. The heterogeneity and stability of this nanocatalyst were studied by hot filtration and the AAS technique. Also, the reused catalyst was characterized by the SEM, EDS, AAS and BET techniques.

Synthesis of 5-substituted 1H-tetrazoles and oxidation of sulfides by using boehmite nanoparticles/nickel-curcumin as a robust and extremely efficient green nanocatalyst

Nickel-anchored curcumin-functionalized boehmite nanoparticles (BNPs@Cur-Ni) as a robust and versatile nanocatalyst was synthesized and well-characterized by using Fourier transform infrared (FT-IR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), X-ray mapping, thermogravimetric analysis (TGA), differential thermal analysis (DTA), Brunauer–Emmett–Teller (BET), X-ray diffraction (XRD), and inductively coupled plasma optical emission spectroscopy (ICP-OES). The synthesis of 5-substituted 1H-tetrazoles and the oxidation of sulfides were conducted by BNPs@Cur-Ni with excellent turnover number (TON) and turnover frequency (TOF) outcomes. Also, the catalyst was reused for several sequential runs without Ni leaching or decreasing in reaction yield. Utilizing the curcumin and boehmite with a natural source as well as poly(ethylene glycol) (PEG) as a solvent in this simple protocol can be based on green chemistry rules.

L -Proline: An Efficient Organocatalyst for the Synthesis of 5-Substituted 1 H -Tetrazoles via [3+2] Cycloaddition of Nitriles and Sodium Azide

A simple and efficient route for the synthesis of a series of 5-substituted 1 H -tetrazoles using l -proline as a catalyst from structurally diverse organic nitriles and sodium azide is reported. The prominent features of this environmentally benign, cost effective, and high-yielding l -proline-catalyzed protocol includes simple experimental procedure, short reaction time, simple workup, and excellent yields making it a safer and economical alternative to hazardous Lewis acid catalyzed methods. The protocol was successfully applied to a broad range of substrates, including aliphatic and aryl nitriles, organic thiocyanates, and cyanamides.

COMPOUNDS USEFUL AS CSF1 MODULATORS

This invention relates to novel compounds and to pharmaceutical compositions comprising the novel compounds. More specifically, the invention relates to compounds useful as Colony Stimulating Factor 1 Receptor (cFMS) modulators (e.g. cFMS inhibitors). This invention also relates to processes for preparing the compounds, uses of the compounds in treatment and methods of treatment employing the compounds. Specifically, the invention relates to the use of the compounds for the treatment of cancer and autoimmune diseases.

New energetic polynitrotetrazoles

This combined experimental, theoretical and comparative study details the syntheses and chemical characterisation of two new energetic polynitromethyl tetrazole derivatives, namely, 2-(2-nitro-2-azapropyl)-5-(trinitromethyl)-2H-tetrazole and its fluorine-containing analogue 2-(2-nitro-2-azapropyl)-5-(fluorodinitromethyl)-2H-tetrazole. Their crystal structures and energetic behaviour are compared to those of their starting materials, the ammonium salts of the corresponding 5-(polynitromethyl)-2H-tetrazoles. Additionally, the crystal structures of two further related polynitrotetrazoles are presented.

Tetrazolylhydrazides as selective fragment-like inhibitors of the JumonjiC-domain-containing histone demethylase KDM4A

The JumonjiC-domain-containing histone demethylase 2A (JMJD2A, KDM4A) is a key player in the epigenetic regulation of gene expression. Previous publications have shown that both elevated and lowered enzyme levels are associated with certain types of cancer, and therefore the definite role of KDM4A in oncogenesis remains elusive. To identify a novel molecular starting point with favorable physicochemical properties for the investigation of the physiological role of KDM4A, we screened a number of molecules bearing an iron-chelating moiety by using two independent assays. In this way, we were able to identify 2-(1H-tetrazol-5-yl)acetohydrazide as a novel fragment-like lead structure with low relative molecular mass (Mr=142 Da), low complexity, and an IC50 value of 46.6 μm in a formaldehyde dehydrogenase (FDH)-coupled assay and 2.4 μm in an antibody-based assay. Despite its small size, relative selectivity against two other demethylases could be demonstrated for this compound. This is the first example of a tetrazole group as a warhead in JMJD demethylases. Anchor fragment: To develop non-promiscuous metalloenzyme inhibitors, a metal-complexing acetohydrazide group was integrated in a tetrazolyl fragment, which can be matured into a scaffold to promote further selectivity at the ligand backbone binding site of these emerging drug targets.