- Heteropolyacid catalyzed click synthesis of 5-substituted 1H-tetrazoles from [bmim]N3 and nitriles under solvent-free conditions
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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
- Fazeli, Azadeh,Oskooie, Hossein A.,Beheshtiha, Yahya S.,Heravi, Majid M.,Valizadeh, Hassan,Bamoharram, Fatemeh F.
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- Challenging the Limits of Nitro Groups Associated with a Tetrazole Ring
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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.
- Yu, Qiong,Imler, Gregory H.,Parrish, Damon A.,Shreeve, Jean'Ne M.
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- Energetic high-nitrogen compounds: 5-(trinitromethyl)-2 H -tetrazole and -tetrazolates, preparation, characterization, and conversion into 5-(dinitromethyl)tetrazoles
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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.
- Haiges, Ralf,Christe, Karl O.
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- Computer design, synthesis, and bioactivity analyses of drugs like fingolimod used in the treatment of multiple sclerosis
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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
- Turgut, Gurbet ?elik,Doyduk, Do?ukan,Y?ld?r?r, Y?lmaz,Yavuz, Serkan,Akdemir, Atilla,Di?li, Ali,?en, Alaattin
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- Magnetization of biochar nanoparticles as a novel support for fabrication of organo nickel as a selective, reusable and magnetic nanocatalyst in organic reactions
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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.
- Moradi, Parisa,Hajjami, Maryam
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p. 2981 - 2994
(2021/02/26)
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- Synthesis of 5-substituted 1H-tetrazoles and oxidation of sulfides by using boehmite nanoparticles/nickel-curcumin as a robust and extremely efficient green nanocatalyst
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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.
- Jani, Muhammed Ali,Bahrami, Kiumars
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- L -Proline: An Efficient Organocatalyst for the Synthesis of 5-Substituted 1 H -Tetrazoles via [3+2] Cycloaddition of Nitriles and Sodium Azide
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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.
- Bhagat, Saket B.,Telvekar, Vikas N.
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supporting information
p. 874 - 879
(2018/02/16)
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- COMPOUNDS USEFUL AS CSF1 MODULATORS
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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.
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Paragraph 00771; 00772; 00773
(2016/04/26)
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- New energetic polynitrotetrazoles
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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.
- Kettner, Marcos A.,Klap?tke, Thomas M.
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p. 3755 - 3765
(2015/03/04)
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- Tetrazolylhydrazides as selective fragment-like inhibitors of the JumonjiC-domain-containing histone demethylase KDM4A
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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.
- Rüger, Nicole,Roatsch, Martin,Emmrich, Thomas,Franz, Henriette,Schüle, Roland,Jung, Manfred,Link, Andreas
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p. 1875 - 1883
(2015/11/10)
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- Eco-friendly synthesis of guanidinyltetrazole compounds and 5-substituted 1H-tetrazoles in water under microwave irradiation
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We have developed simple, short time, cost effective, purification of products by non-chromatographic methods and environmentally benign protocol for the synthesis of guanidinyltetrazoles and 5-substituted 1H-tetrazoles derivatives via [2,3]cyclo-addition
- El Remaily, Mahmoud Abd El Aleem Ali Ali,Mohamed, Shaaban K.
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p. 270 - 275
(2014/01/06)
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- Green synthesis of 5-substituted-1H-1,2,3,4-tetrazoles and 1-sustituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition by reusable immobilized AlCl3on -Al2O3
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We report the effectiveness of the surface modified γ-Al2O3which is reusable, efficient, catalytic, safe and environmentally acceptable procedure for the conversion of both alkyl and aryl nitriles into the corresponding 5-substituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition with sodium azide in excellent yields at mild reaction conditions (50 ° C). The catalyst also afforded 1-substituted-1H-1,2,3,4-tetrazoles by the reaction of amines, sodium azide and triethyl orthoformate. The catalyst could be recycled and was reused eleven runs without losing its activity.
- Nanjundaswamy, Hemmaragala Marishetty,Abrahamse, Heidi
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p. 2137 - 2150
(2015/01/09)
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- β-Cyclodextrin-mediated highly efficient [2+3] cycloaddition reactions for the synthesis of 5-substituted 1H-tetrazoles
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A β-cyclodextrin-promoted [2+3] cycloaddition reaction between nitriles and sodium azide in the presence of ammonium chloride in DMF at 120 °C is reported, affording various 5-substituted 1H-tetrazoles in good to excellent yields in short reaction times. The presence of β-CD renders the formation of a precipitate-like gel in the reaction media when heated. No precipitation occurs in the absence of NaN3 and NH4Cl. The precipitation responses with other salts such as LiCl and NiCl2 were weaker than with NH4Cl. In the present paper the application of supramolecular aggregates is reported for the [2+3] cycloaddition reaction. β-Cyclodextrin can be recovered and reused without any significant loss of activity.
- Patil, Dipak R.,Wagh, Yogesh B.,Ingole, Pravin G.,Singh, Kripal,Dalal, Dipak S.
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p. 3261 - 3266
(2013/10/01)
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- InCl3-catalyzed [2+3] cycloaddition reaction: A rapid synthesis of 5-substituted 1H-tetrazole under microwave irradiation
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A series of 5-substituted 1H-tetrazole were efficiently prepared by InCl3 catalyzed (10 mol %) from structurally divert organic nitriles with sodium azide under the influence of microwave irradiation. The present protocol was successfully applied to the aliphatic, aryl, benzylic and heterocyclic nitriles and corresponding 5-substituted 1H-tetrazole were obtained in good to excellent yield (70-96%). This method gives remarkable advantages such as short reaction time, simple work-up procedure and economical beneficial.
- Patil, Vijay S.,Nandre, Kamalakar P.,Borse, Amulrao U.,Bhosale, Sidhanath V.
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experimental part
p. 1145 - 1152
(2012/05/31)
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- Inhibition of the production of the Pseudomonas aeruginosa virulence factor pyocyanin in wild-type cells by quorum sensing autoinducer-mimics
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Pseudomonas aeruginosa is a notorious human pathogen associated with a range of life-threatening nosocomial infections. There is an increasing problem of antibiotic resistance in P. aeruginosa, highlighted by the emergence of multi-drug resistant strains.
- Morkunas, Bernardas,Galloway, Warren R. J. D.,Wright, Megan,Ibbeson, Brett M.,Hodgkinson, James T.,O'Connell, Kieron M. G.,Bartolucci, Noemi,Valle, Martina Della,Welch, Martin,Spring, David R.
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p. 8452 - 8464
(2013/01/15)
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- Amine salt-catalyzed synthesis of 5-substituted 1H-tetrazoles from nitriles
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The [3+2] cycloaddition reaction between sodium azide and various organic nitriles proceeds smoothly in the presence of amine salts as catalyst in dimethylformamide. The corresponding 5-substituted 1-H tetrazoles were obtained under mild condition in good to excellent yields. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Taylor & Francis Group, LLC.
- Zhou, Yi,Yao, Cheng,Ni, Renjie,Yang, Gaowen
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experimental part
p. 2624 - 2632
(2010/10/03)
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- Heterocyclic-substituted alkylamide acat inhibitors
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Pharmaceutically useful compounds having ACAT inhibitory activity of the formula wherein n is 0, 1, or 2, for X other than tetrazole and n = 2 then R2 = R3 = H; R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, a heteroaromatic group or a hydrocarbon group having from one to 18 carbon atoms; R2 and R3 are hydrogen, halo, hydroxy, alkyl, alkenyl, cycloalkyl, phenyl, substituted phenyl, a heteroaryl, or form a spiroalkyl group; x is a 5-membered heteromonocyclic group containing at least one to four heteroatoms selected from the group consisting of isothiazole, oxazole, thiazole, imidazole, furan, thiophene, pyrrole, tetrazole, 1,2,3-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and 1,2,4-oxadiazole said heteromonocyclic group being unsubstituted or substituted at any available position along the ring,
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- Tetrazole compounds and pharmaceutical agents containing such derivative
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PCT No. PCT/JP96/03801 Sec. 371 Date Jun. 29, 1998 Sec. 102(e) Date Jun. 29, 1998 PCT Filed Dec. 26, 1996 PCT Pub. No. WO97/24339 PCT Pub. Date Oct. 7, 1997A tetrazole derivative of formula (I) wherein R is H, alkyl, alkoxy, carbocyclic ring, alkyl or alkoxy substituted by carbocyclic ring; AA1 and AA2 is a bond or and respectively, or AA1 and AA2, together, may have the formula (a); and Y is formula (b) wherein the Tet ring is tetrazole; Z is alkylene, alkenylene, O, S, SO, SO2, NR26, methylene in alkylene replaced by O, S, -SO-, -SO2- or -NR26-; and E is H, alkyl, or COOR27.
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- Inhibitors of acyl-CoA:cholesterol O-acyltransferase. Synthesis and pharmacological activity of (±)-2-dodecyl-α-phenyl-N-(2,4,6- trimethoxyphenyl)-2H-tetrazole-5-acetamide and structurally related tetrazole amide derivatives
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A series of tetrazole amide derivatives of (±)-2-dodecyl-α-phenyl-N- (2,4,6-trimethoxyphenyl)-2H-tetrazole-5-acetamide (1) was prepared and evaluated for their ability to inhibit acyl-CoA: cholesterol O- acyltransferase (ACAT) in vitro and to lower plasma total cholesterol in vivo. For this series of compounds, our objective was to systematically replace substituents appended to the amide and tetrazole moieties of 1 with structurally diverse functionalities and assess the effect that these changes have on biological activity. The ensuing structure-activity relationship (SAR) studies identified aryl (7b) and heteroaryl (7f,g) replacements for 2,4,6-trimethoxyphenyl that potently inhibit liver microsomal and macrophage ACAT in vitro and exhibit good cholesterol lowering activity (56-66% decreases in plasma total cholesterol at 30 mg/kg), relative to 1, when compared in the acute rat model of hypercholesterolemia. Replacement of the α-phenyl moiety with electron-withdrawing substituents (13e-h), however, significantly reduced liver microsomal ACAT inhibitory activity (IC50 > 1 μM). This is in contrast to electron-donating substituents (13ij,m-q), which produce IC50 values ranging from 5 to 75 nM in the hepatic microsomal assay. For selected tetrazole amides (1, 7b, 13n,o), reversing the order of substituents appended to the 2- and 5-positions in the tetrazole ring (36a- d), in general, improved macrophage ACAT inhibitory activity and provided excellent cholesterol-lowering activity (ranging from 65% to 77% decreases in plasma total cholesterol at 30 mg/kg) in the acute rat screen. The most potent isomeric pair in this set of unsubstituted methylene derivatives (13n and 36a) caused adrenocortical cell degeneration in guinea pigs treated with these inhibitors. In contrast, adrenal glands taken from guinea pigs treated with the corresponding α-phenyl-substituted analogs (7b and 36c) were essentially unchanged compared to untreated controls. Subsequent evaluation of 7b and 36c in a rabbit bioassay showed that both compounds and/or their metabolites were present in plasma after oral dosing. Unlike 7b and 36c, compound 1 and related 2,4,6-trimethoxyanilides (13j, 30c,d) showed poor oral activity in the rabbit bioassay. Nevertheless, in cholesterol-fed rabbits, both systemically available (7b, 36c) and poorly absorbed inhibitors (1, 36d) were more effective in lowering plasma total cholesterol than the fatty acid amide CI-976.
- O'Brien,Sliskovic,Picard,Lee,Purchase II,Roth,White,Anderson,Mueller,Bocan,Bousley,Hamelehle,Homan,Lee,Krause,Reindel,Stanfield,Turluck
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p. 2354 - 2366
(2007/10/03)
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- Amide tetrazole ACAT inhibitors
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Amide tetrazoles of the formula STR1 wherein aryl includes phenyl and naphthyl, unsubstituted or substituted, X is =O, =N--R5, or --NR3 R4, where R2, R4, and R5 include alkyl and alkoxy and
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- Isoxazolyl-substituted alkyl amide ACAT inhibitors
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Pharmaceutically useful compounds having ACAT inhibitory activity of the formula STR1 wherein n is 0, 1, or 2, for X other than tetrazole and n=2 then R2 =R3 =H; R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, a heteroaromatic group or a hydrocarbon group having from one to 18 carbon atoms; R2 and R3 are hydrogen, halo, hydroxy, alkyl, alkenyl, cycloalkyl, phenyl, substituted phenyl, a heteroaryl, or form a spiroalkyl group; X is a heteromonocyclic 5-membered ring containing one to four heteroatoms, said heteroatoms being nitrogen, oxygen or sulfur, and combination thereof; and R4 is a hydrocarbon group having from one to 20 carbon atoms are described as well as methods of their manufacture.
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