Tag: M.W=50-100

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

Al-Saadi, Abdulaziz A. published the artcileUnderstanding the Influence of Electron-Donating and Electron-Withdrawing Substituents on the Anticorrosive Properties of Imidazole: A Quantum-Chemical Approach, Category: imidazoles-derivatives, the main research area is imidazole substituent effect protonation mol structure HOMO LUMO.

The nature and position of electron-donating and electron-withdrawing substituents are believed to play a major role on the corrosion inhibition properties in small organic mols. In this study, the substituent effect on the imidazoles anticorrosive properties has been explored theor. using the d. functional theory performed at the B3LYP/6-311++G(d,p) level. A wide spectrum of substituents including NH2, COOH, I, Br, Cl, F, CN, F, OH, OCH3, NO2, C6H5 and SH groups has been explored in the aqueous medium, and the different possible substitution positions have been investigated. Frontier MOs and quantum-chem. reactivity descriptors were calculated for the neutral and protonated forms of imidazole derivative While the energy gaps, electronegativity and global hardness values showed a very good agreement with the corrosion inhibition performance reported from previous exptl. work for imidazoles, the electrophilicity and mol. volume parameters were found less consistent. This study concluded that the amino and nitro groups, in particular those at C2 and C4 positions, exhibit prominent corrosion inhibition performance. The electron-releasing Ph and methoxy substituents could also play a potential role in enhancing the anticorrosive properties of imidazole.

Arabian Journal for Science and Engineering published new progress about Atomic charge. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Category: imidazoles-derivatives.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Kurzepa, M. published the artcileTheoretical studies on tautomerism and IR spectra of C-5 substituted imidazoles, Safety of 5-Fluoro-1H-imidazole, the main research area is theor tautomerism IR substituted imidazole.

Total energy, Gibbs free energy, the highest π and σ electronic states, and IR spectra were calculated for twelve C-5 substituted imidazoles at the MP2/6-311++G** level. The COOH and BH2 groups stabilize strongly the N1-H tautomer, the F and OH groups stabilize strongly the N3-H tautomer, whereas the NH2 and NO2 groups favors the N3-H tautomer with a similar, medium strength. The calculated IR spectra of the imidazoles studied reveal differences between the two tautomers, but they do not follow the order of derivatives emerging from the energetics.

Journal of Molecular Structure published new progress about Amino group. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Safety of 5-Fluoro-1H-imidazole.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Guemues, Selcuk published the artcileSubstituent effect on the aromaticity of 1,3-azole systems, Application of 5-Fluoro-1H-imidazole, the main research area is oxazole imidazole thiazole substituent effect aromaticity.

The effects of substituent type and position on the aromaticity of certain derivatives of oxazole, imidazole and thiazole have been theor. investigated by using d. functional theory at the levels of B3LYP/6-31G(d,p) and B3LYP/6-31++G(d,p) methods. The second heteroatom substitution decreased aromaticity of furan, pyrrole and thiophene. The decreased aromaticity was gained back to some extent by the substitution of strong electron withdrawing groups or atoms (NO2 and F). Nucleus-independent chem. shift (NICS) data have been considered to determine the aromaticity of the systems. The most effective substitution to enhance the aromaticity has been calculated to be at position 4. The variation of the bond lengths of the main skeleton supported the findings through NICS calculations The frontier MO energies have also been reported to draw a general correlation between these energies and the aromaticity of the system.

Heterocyclic Communications published new progress about Aromaticity. 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

Xing, Jing published the artcileRational design of 5-((1H-imidazol-1-yl)methyl)quinolin-8-ol derivatives as novel bromodomain-containing protein 4 inhibitors, Computed Properties of 30086-17-0, the main research area is imidazolylmethylquinolinol bromodomain containing protein 4 inhibitor; 8-OH-Quinoline; Anti-cancer activity; Bromodomain-containing protein 4; Computer-aided drug design; Early ADME/T evaluation; Rational hit-to-lead optimization.

Bromodomain-containing protein 4 (BRD4), an epigenetic reader of acetyl lysine, has emerged as a promising therapeutic target for many diseases including cancer, inflammation and heart failure. The previous study reported that nitroxoline, an FDA approved antibiotic, showed potential BRD4 inhibitory activity and antiproliferation activity against leukemia cell lines. In this study, the authors further explored the structure-activity relationship (SAR) around nitroxoline and employed the previously developed machine learning based activity scoring function BRD4LGR for further anal. To improve the cellular level activity, physico-chem. properties were optimized using computational approaches. Then the candidates were tested for their ADME/T profiles. Finally, based on this rational hit-to-lead optimization strategy, 3 drug-like BRD4 inhibitors were obtained, with different profiles on cell line selectivity for multiple myeloma, leukemia and triple neg. breast cancer. Further mechanism study showed these compounds could down-regulate c-Myc to inhibit cancer cell growth. This work illustrates the application of multiple computer-aided drug design techniques in a hit-to-lead optimization scenario, and provides novel potent BRD4 inhibitors with different phenotype propensities for future cancer treatment.

European Journal of Medicinal Chemistry published new progress about Antitumor agents. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Computed Properties of 30086-17-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

De Clercq, Erik published the artcileFluoroimidazoles as antiviral agents and inhibitors of polynucleotide biosynthesis, SDS of cas: 30086-17-0, the main research area is fluoroimidazole virus nucleotide.

4-Fluoroimidazole (4-FI) [30086-17-0], 4-fluoroimidazole-5-carboxylic acid (4-FIC) [42309-90-0], 4-fluoroimidazole-5-carboxamide (4-FICA ) [33300-35-5], and 5-fluoro-1-β-D-ribofuranosylimidazole-4-carboxamide (5-FICAR) [56766-95-1] were studied for their inhibitory effects on viral cytopathogenicity in 10 assay systems encompassing nearly all major virus groups. Ribavirin (1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide) [36791-04-5], 5-AICAR (5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide) [2627-69-2], and poly (I)-poly (C) [24939-03-5] were included as reference materials. Although the antiviral activities of ribavirin and the fluoroimidazoles varied considerably from 1 system to another, the relative order of activity remained constant: ribavirin > 5-FICAR > 5-AICAR > 4-FICA. 4-FIC and 4-FI were inactive. Poly (I)-poly (C) showed a spectrum of antiviral activity that differed totally from that of 5-FICAR and the other compounds Unlike 5-AICAR, both 5-FICAR and ribavirin inhibited cellular DNA and RNA synthesis at concentrations which coincided quite well with those inhibiting viral cytopathogenicity. Hence, 5-FICAR and ribavirin may owe their broad-spectrum antiviral activity to inhibition of nucleic acid synthesis in the infected cell.

Life Sciences published new progress about Antiviral agents. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, SDS of cas: 30086-17-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Lingscheid, Yves published the artcileDetermination of inter-ionic and intra-ionic interactions in a monofluorinated imidazolium ionic liquid by a combination of X-ray crystallography and NOE NMR spectroscopy, Category: imidazoles-derivatives, the main research area is inter ionic intra interaction monofluorinated imidazolium liquid; X ray crystallog NOE NMR spectroscopy.

We report the very first application of a Transient 1D 1H{19F} NOE NMR experiment in neat ionic liquids In comparison with classical 2D HOESY NMR spectroscopy, a substantial reduction in measurement time is gained with comparable quality and information content of the spectra. In combination with classical X-ray crystallog., we have applied this technique for the determination of inter-ionic distances (i.e. probabilities of presence) utilizing an ionic liquid containing a monofluorinated imidazolium cation. Copyright © 2017 John Wiley & Sons, Ltd.

Magnetic Resonance in Chemistry published new progress about Crystal structure. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Category: imidazoles-derivatives.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Takeuchi, Yoshio published the artcileAdjacent lone pair (ALP) effects in heteroaromatic systems. 2. Isotope exchange of ring hydrogens in nitro- and fluoroimidazoles, Formula: C3H3FN2, the main research area is adjacent lone pair effect; hydrogen exchange nitroimidazole fluoroimidazole; imidazole nitro fluoro exchange.

The ring protons of nitro- and fluoroimidazoles (and their N-Me derivatives) undergo base-catalyzed exchange in D2O by a combination of carbanion (C) and ylide (Y) pathways, which involve proton abstraction from the neutral imidazole species and from the imidazolium ion, resp. In 4-substituted imidazoles, C exchange occurs more readily at C-5 than at C-2, log kC correlating with σo° for the NH- and with σp° for the N-Me series. For 1-methyl-4-nitroimidazole, t1/2 = 2 min at C-5 (50°, 0.2 N NaOD). In 1-methyl-5-X-imidazoles, exchange at C-4 occurs only via the Y pathway, carbanion formation in the neutral species being retarded by the adjacent lone pair (ALP) effect at N-3. The same effect is seen in the lack of C exchange at C-4 in 1-methylimidazoles. The ALP effect is considerably weaker or nonexistent at C-2. Most exchanges across the ring show correlations of log k with ςm°. 4-Alkylimidazoles (but not 1,4-dialkylimidazoles) show enhanced C exchange at C-5, which may result from the existence of a trace concentration of the ketimine tautomer. Enhanced exchange at C-5 in 2-fluorohistidine is ascribed to a combination of the ketimine effect, C exchange involving catalysis by OH and intramol. general-base catalysis by the side-chain primary-amine function. The use of buffer catalysis for the T labeling of poorly reactive imidazoles is described.

Journal of Organic Chemistry published new progress about Exchange 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

Ogretir, Cemil published the artcileAM1 and PM3 study of the protonation tautomerization and valence tautomerization of some 4-substituted imidazoles, Product Details of C3H3FN2, the main research area is MO protonation tautomerization substituted imidazole; valence tautomerization substituted imidazole.

The gas-phase geometries, relative stabilities, ionization potentials and proton affinities of the different tautomers of some 4-substituted imidazoles and their N-Me derivatives were calculated with full geometry optimization. The predominance of the a (i.e. 1H-form) form with an electron-acceptor group at the 4-position over the b (i.e. 3H-form) form and the predominance of the b (i.e. 3H-form) form with an electron-donor group at the 4-position over the a (i.e. 1H-form) form were confirmed. A correlation between exptl. obtained acidity constants, pKa, and calculated proton affinities was detected.

Journal of Molecular Structure: THEOCHEM published new progress about AM1 (molecular orbital method). 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

Raczynska, E. D. published the artcileApplication of semiempirical method (AM1) to the study of tautomeric equilibria in the gas phase for simple compounds containing the amidine group: 4(5)-substituted imidazoles, HPLC of Formula: 30086-17-0, the main research area is MO gas phase tautomeric equilibrium imidazole; protonation amidine imidazole derivative; acid base equilibrium amidine imidazole derivative.

Semiempirical method (AM1) has been used to predict the tautomeric equilibrium constants (pKT) in the gas phase for 4(5)-substituted imidazoles. The pKT values have been calculated on the basis of heats of formation of individual tautomers. In calculations it has been assumed that the TΔS term has the same value for both tautomers. For comparison, the pKT values have also been estimated on the basis of the calculated (by AM1) proton affinities of N-methyl-4- and 5-substituted imidazoles. Both estimations give almost the same pKT values. Obtained results are compared with those found in solution Comparison shows that the gas-phase substituent effects do not reproduce well those in solution To find an explanation of this observation, the influence of rotational isomerism of substituent on the tautomeric equilibrium constant has been studied. Proton affinities and deprotonation enthalpies of 4- and 5-substituted imidazoles have also been calculated For unsubstituted imidazole, 4(5)-methyl-imidazole and their N-Me derivatives they are compared with those exptl. obtained. Errors are considerably smaller than the average errors of AM1 method for nitrogen acids and bases.

Analytica Chimica Acta published new progress about Acid-base equilibrium. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, HPLC of Formula: 30086-17-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem