Category: imidazoles-derivatives

Morishima, Isao published the artcileProton NMR study of hemoproteins. Ionization and orientation of iron-bound imidazole in methemoglobin and metmyoglobin, Application of 5-Fluoro-1H-imidazole, the main research area is methemoprotein imidazolyl ionization orientation; imidazolylmethemoprotein ligand ionization orientation; imidazolylmetHb ionization heme orientation; imidazolylmetmyoglobin ionization heme orientation; heme orientation imidazolylmethemoprotein ligand.

Characteristics of imidazole derivatives bound to metHb and metmyoglobin (MetMb) were investigated by H NMR spectroscopy with special regard to the ionization of the imino proton and orientation of the imidazole ring in the heme crevice. The hyperfine-shifted heme Me resonances of MetMb complexes with imidazole, 4-methylimidazole, and triazole were pH dependent, whereas those of the N-methylimidazole complex were pH independent. The pH-dependent shifts in the former complexes were attributed to the deprotonation of the imino proton of imidazole derivatives bound to the heme Fe. In contrast, MetMb complexes with 4-nitroimidazole and 4-fluoroimidazole, both of which have the ionizable NH proton, did not exhibit such pH-dependent shifts, indicating restricted orientation of the Fe-bound 4-nitroimidazole and 4-fluoroimidazole in the heme crevice, where the imino proton is not exposed to the solvent sphere. In the MetMb-imidazole complex, however, pH dependence of the hyperfine shifts was observed, in contrast to the case of imidazole-MetMb. This was also interpreted as arising from the specific orientation of the Fe-bound exogenous imidazole in the MetMb heme pocket. Two sets of heme Me proton resonances were detected for the 4-fluoroimidazole-MetMb complex and these were attributed to the 2 tautomeric forms of the Fe-bound 4-fluoroimidazole. The relative proportion of the 2 tautomers was dependent on both pH and temperature The temperature dependence of the hyperfine shifts of the 2 species indicated that they are in a single spin state.

Biochimica et Biophysica Acta, Protein Structure published new progress about Ionization. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Application of 5-Fluoro-1H-imidazole.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Gesmundo, Nathan J. published the artcileNanoscale synthesis and affinity ranking, Product Details of C8H8N2O, the main research area is structure drug discovery.

Most drugs are developed through iterative rounds of chem. synthesis and biochem. testing to optimize the affinity of a particular compound for a protein target of therapeutic interest. This process is challenging because candidate mols. must be selected from a chem. space of more than 1060 drug-like possibilities1, and a single reaction used to synthesize each mol. has more than 107 plausible permutations of catalysts, ligands, additives and other parameters2. The merger of a method for high-throughput chem. synthesis with a biochem. assay would facilitate the exploration of this enormous search space and streamline the hunt for new drugs and chem. probes. Miniaturized high-throughput chem. synthesis3-7 has enabled rapid evaluation of reaction space, but so far the merger of such syntheses with bioassays has been achieved with only low-d. reaction arrays, which analyze only a handful of analogs prepared under a single reaction condition8-13. High-d. chem. synthesis approaches that have been coupled to bioassays, including on-bead14, on-surface15, on-DNA16 and mass-encoding technologies17, greatly reduce material requirements, but they require the covalent linkage of substrates to a potentially reactive support, must be performed under high dilution and must operate in a mixture format. These reaction attributes limit the application of transition-metal catalysts, which are easily poisoned by the many functional groups present in a complex mixture, and of transformations for which the kinetics require a high concentration of reactant. Here the authors couple high-throughput nanomole-scale synthesis with a label-free affinity-selection mass spectrometry bioassay. Each reaction is performed at a 0.1-M concentration in a discrete well to enable transition-metal catalysis while consuming less than 0.05 mg of substrate per reaction. The affinity-selection mass spectrometry bioassay is then used to rank the affinity of the reaction products to target proteins, removing the need for time-intensive reaction purification This method enables the primary synthesis and testing steps that are critical to the invention of protein inhibitors to be performed rapidly and with minimal consumption of starting materials.

Nature (London, United Kingdom) published new progress about Chemical library. 82090-52-6 belongs to class imidazoles-derivatives, name is Imidazo[1,2-a]pyridin-2-ylmethanol, and the molecular formula is C8H8N2O, Product Details of C8H8N2O.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Dolensky, Bohumil published the artcileSynthesis of 4,5-difluoroimidazole, Formula: C3H3FN2, the main research area is imidazole difluoro preparation; photochem Schiemann reaction aminoimidazole fluorination.

5-Fluoroimidazole-4-carboxylic acid Et ester 3 was converted to the corresponding hydrazide 4 in 81% yield. Oxidation of the hydrazide to the carbonyl azide 5 (88%) and Curtius rearrangement in t-Bu alc. produced 94% 4-t-butyloxycarbonylamino-5-fluoroimidazole 6. Dissolution of the t-Bu carbamate in 50% HBF4, in situ diazotization of the resulting amine, and irradiation produced the target compound 1 in 36% yield from 6 by the photochem. Schiemann reaction.

Journal of Fluorine Chemistry published new progress about Curtius reaction. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Formula: C3H3FN2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Catalan, Javier published the artcileSubstituent effects on proton affinities: through bonds or through space mechanism?, Product Details of C3H3FN2, the main research area is MO pyrazole imidazole; protonation energy pyrazole imidazole; lone pair orbital energy heterocycle.

INDO calculations of the protonation energies and lone pair orbital energies of twenty pyrazoles and twenty imidazoles have been carried out in order to ascertain the mechanism of the substituent effect; Me, cyano, fluoro, amino, and nitro substituents have been examined The nitro group shows a special behavior. The importance of optimizing the geometry and the reasons for the anomaly shown by the nitro derivatives are discussed.

Heterocycles published new progress about Electronic state. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Product Details of C3H3FN2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Thomann, Andreas published the artcileMicrowave-assisted synthesis of 4-substituted 2-methylthiopyrimidines, Recommanded Product: 5,6-Dimethoxy-1H-benzo[d]imidazole, the main research area is chloromethylthiopyrimidine heterocycle aromatic substitution microwave irradiation; heterocycle substituted methylthiopyrimidine preparation green chem.

Typically, SNAr reactions at 4-chloro-2-methylthiopyrimidine are carried out employing DMF and sodium hydride under inert gas as well as prolonged reaction times. Herein, we describe a mild and rapid microwave-assisted synthesis to achieve 4-substituted 2-methylthiopyrimidines from the corresponding chlorine precursor. Moderate to excellent yields were obtained in a green chem. fashion requiring only few minutes of reaction time.

Synlett published new progress about Green chemistry. 72721-02-9 belongs to class imidazoles-derivatives, name is 5,6-Dimethoxy-1H-benzo[d]imidazole, and the molecular formula is C9H10N2O2, Recommanded Product: 5,6-Dimethoxy-1H-benzo[d]imidazole.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Kirk, Kenneth L. published the artcileBiochemistry and pharmacology of ring-fluorinated imidazoles, Recommanded Product: 5-Fluoro-1H-imidazole, the main research area is fluoroimidazole pharmacol; histadine fluoro derivative pharmacol; imidazole fluoro derivative pharmacol.

Concentrations of 2-fluorohistidine (I) [57212-36-9] ≤10-5 M were bacteriostatic with Escherichia coli, but the inhibition was reversed by the addition of L-histidine [71-00-1]. I also showed antiviral activity in cell cultures. Thyrotropin-releasing-factor (TRF) [24305-27-9] and luteinizing hormone-releasing factor (LHRF) [9034-40-6] were synthesized with I and 4-fluorohistidine [57372-70-0] residues as replacement for the histadine residues; while the 4-fluoro analogs were inactive, those containing I showed 20-30% activity. 4-Fluorohistadine did not show bacterostatic or antiviral activity, but it was a substrate for bacterial histidine decarboxylase [9024-61-7]. Neither 4-fluorourocanic acid [60010-44-8] or 2-fluorourocanic acid [60010-46-0] was a substrate for urocanase [9014-58-8], but the 2-fluoro derivative of urocanic acid was an inhibitor of the enzyme. 2-Fluorohistamine [50581-18-5] had good affinity for H1 histamine receptors in guinea pig ileum.

ACS Symposium Series published new progress about Antihistamines. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Recommanded Product: 5-Fluoro-1H-imidazole.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Linz, Sabine published the artcileDesign, synthesis and dopamine D4 receptor binding activities of new N-heteroaromatic 5/6-ring Mannich bases, Category: imidazoles-derivatives, the main research area is dopamine D4 receptor antagonist Mannich bases SAR preparation.

A series of phenylpiperazine-methyl-substituted 1H-pyrrolo[2,3-c]pyridine, imidazo[1,2-c]-, pyrrolo[2,3-d]- and pyrrolo[3,2-d]pyrimidines were prepared as selective dopamine D4-ligands. The pyrrolo[2,3-d]pyrimidine derivatives 12d (I) (K i = 1,9 nM) and 34d (II)(K i = 2,4 nM) as well as the pyrrolo[3,2-d]pyrimidine Mannich base 49f (III) (K i = 2,8 nM) showed high dopamine D4 receptor activity superior to the atypical antipsychotic agent clozapine.

Bioorganic & Medicinal Chemistry published new progress about Antipsychotics. 274-78-2 belongs to class imidazoles-derivatives, name is Imidazo[1,2-c]pyrimidine, and the molecular formula is C6H5N3, Category: imidazoles-derivatives.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Dumanovic, D. published the artcileSimultaneous determination of N-substituted and N-substituted nitroazoles, and criteria for their identification. III. Chromatographic separation and polarographic determination of halonitroimidazoles, Name: 5-Bromo-2-methyl-4-nitroimidazole, the main research area is halonitroimidazole mixture polarog chromatog; chromatog thin layer halonitroimidazole; nitroimidazole halo polarog determination; imidazole halo nitro determination.

Halonitroimidazoles with the NO2 group in the same position are separated for identification by thin-layer chromatog. on unactivated silica gel HF254 in an atm. saturated with the vapor of 1 of 5 developers, the plate then being sprayed with 15% SnCl2 solution in aqueous HCl, dried, sprayed with p-dimethylaminobenzaldehyde solution, and redried. All 4-nitro derivatives give a yellow color and 4(5)- and 5-nitro compounds are yellow-red. Polarog. determination of halonitroimidazoles may be used in all synthetic processes where the azoles were prepared by nitration of haloimidazoles. A sample of the reaction mixture containing ≤10-3M polarog.-active compound and a suitable buffer is polarographed in the presence and absence of 2 ml 10-3M standard solution of the imidazole being determined and the amount imidazole is directly calculated from the observed wave heights. For halonitroimidazoles obtained from 5(4)-halo-4(5)-nitroimidazoles by substitution of the imino H, and when only one N-substituted derivative is present in the reaction mixture, simultaneous polarog. determination of both compounds is possible only in alk. medium. For mixtures on which simultaneous polarog. determination is impossible a sample of the reaction mixture containing 3 × 10-3-10-2M of all polarog.-active compounds is chromatog. separated and the bands are removed, dissolved in water, and then polarographed.

Talanta published new progress about Chromatography. 18874-52-7 belongs to class imidazoles-derivatives, name is 5-Bromo-2-methyl-4-nitroimidazole, and the molecular formula is C4H4BrN3O2, Name: 5-Bromo-2-methyl-4-nitroimidazole.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Poplawska, Magdalena published the artcileDetermination of flibanserin and tadalafil in supplements for women sexual desire enhancement using high-performance liquid chromatography with tandem mass spectrometer, diode array detector and charged aerosol detector, Recommanded Product: 1-(2-Chloroethyl)-1H-benzo[d]imidazol-2(3H)-one, the main research area is flibanserin tadalafil determination counterfeit herbal supplement HPLC mass spectrometry; Adulteration; Charged aerosol detector; Counterfeit herbal supplement; Flibanserin; Unified calibration.

The new compound – flibanserin – begun to appear as a synthetic adulterant in counterfeit herbal supplements used to stimulate women sexual drive. It was detected in 2 samples submitted to the Polish National Medicines Institute for anal. The second sample contained also tadalafil. This study presents the LC method development which enables the determination of flibanserin and tadalafil. It employs 3 different detectors charged aerosol detector (CAD), diode array detector (DAD) and mass spectrometer (MS). The conditions of the elaborated method were optimized to obtain the highest sensitivity and the best resolution, especially the separation of icariin – the natural compound observed often in supplements for sexual disorders. The validation of the method proved good linearity, good accuracy and precision of the measurements recorded by all 3 detectors. Addnl., for CAD data, an alternative calculation method using a unified calibration function was presented and evaluated. It seems that this is the way to overcome the problem of non-availability of the reference standard of a target compound Flibanserin content was quantified using the data of other reference standard (tadalafil). The inaccuracy of proposed indirect determination was found to be ±3%. A statistical evaluation proved that the results obtained with all detection modes and the results calculated using a unified calibration were not significantly different (p > 0.05).

Journal of Pharmaceutical and Biomedical Analysis published new progress about Counterfeiting. 52548-84-2 belongs to class imidazoles-derivatives, name is 1-(2-Chloroethyl)-1H-benzo[d]imidazol-2(3H)-one, and the molecular formula is C9H9ClN2O, Recommanded Product: 1-(2-Chloroethyl)-1H-benzo[d]imidazol-2(3H)-one.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Fujii, Tozo published the artcilePurines. XX. Synthesis of 1-substituted 5-aminoimidazole-4-carboxamidines and related compounds, Recommanded Product: 5-Amino-1-methyl-1H-imidazole-4-carboxamide, the main research area is imidazolecarboxamidine amino; adenine.

Several 1-substituted 5-aminoimidazole-4-carboxamidines I (R = Me, Et, PhCH2, β-D-ribofuranosyl) were prepared from the corresponding N’-alkoxyamidines (R2 = Me, Et, PhCH2) by catalytic hydrogenolysis. In the hydrogenolysis of II using Raney Ni catalyst, addition of one molar equivalent of HCl accelerated the reaction to give I in acceptable yields. The structures of I were confirmed by cyclization to 9-substituted adenines III and by alk. hydrolysis to 1-substituted derivatives of 5-aminoimidazole-4-carboxamide.

Chemical & Pharmaceutical Bulletin published new progress about Hydrogenolysis. 21343-04-4 belongs to class imidazoles-derivatives, name is 5-Amino-1-methyl-1H-imidazole-4-carboxamide, and the molecular formula is C5H8N4O, Recommanded Product: 5-Amino-1-methyl-1H-imidazole-4-carboxamide.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem