Category: 45533-87-7

Handy, Scott T. published the artcileImidazolium ionic liquids: C2 substitution and acidity, Related Products of imidazoles-derivatives, the publication is Proceedings – Electrochemical Society (2006), 548-555, database is CAplus.

Although imidazolium room temperature ionic liquids (RTILs) have found considerable application, they are not the “inert” solvents that they are frequently considered to be. In particular, the 2 position is prone to deprotonation to form a stabilized carbene. Although this can be beneficial, it can also result in unwanted side reactions under basic conditions. We have studied the acidity of this position in substituted and unsubstituted imidazolium RTILs and discovered that even simple Me substitution does not avoid reasonably facile deprotonation at this site.

Proceedings – Electrochemical Society published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C5H8N2O, Related Products of imidazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Handy, Scott T. published the artcileThe 2-Position of Imidazolium Ionic Liquids: Substitution and Exchange, Synthetic Route of 45533-87-7, the publication is Journal of Organic Chemistry (2005), 70(5), 1915-1918, database is CAplus and MEDLINE.

The 2-position of imidazolium cations is known to be relatively acidic, leading to the useful Arduengo-type carbenes. At the same time, the acidity of this site can lead to undesired side reactions when using imidazolium-based ionic liquids as solvents. In this note, we describe the surprisingly facile deuterium exchange at this position and also the synthesis and exchange under modestly basic conditions (triethylamine) of a series of 2-methyl-substituted compounds

Journal of Organic Chemistry published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C5H8N2O, Synthetic Route of 45533-87-7.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Hirohata, R. published the artcileSynthesis of ophidine, Name: (2-Methyl-1H-imidazol-4-yl)methanol, the publication is Proceedings of the International Congress of Biochemistry (1955), 20, database is CAplus.

Ophidine is an anserine-like compound from cobra muscle. Kendo (C.A. 45, 3438c) reported that it is β-alanyl-2-methylhistidine. To confirm this structure, 2-methyl-4(5)-hydroxymethylimidazole (I), m. 114°, was synthesized from NH₄OH, fructose, and AcH. I was converted to the chloromethyl compound (II), m. 125°. AcNHCH(CO₂Et)₂ was condensed with II, yielding Et α-acetamido-α-carbethoxy-2-methyl-4(5)-imidazolepropionate (III), m. 122°. III was hydrolyzed and decarboxylated to 2-methylhistidine (IV), m. 231°, which was acetylated and resolved by means of acylase 1. The resulting L-IV with phthaloyl-β-alanyl chloride in the presence of NEt₃ at -10° yielded phthaloyl-β-alanyl-2-methylhistidine (V), m. 240°. By treating V with N₂H₄.H₂O solution 2 days, the phthaloyl group was detached, and β-alanyl-2-methylhistidine, m. 249°, was obtained. It gave no depression in m.p. when mixed with natural ophidine. Few exptl. details are given.

Proceedings of the International Congress of Biochemistry published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C5H8N2O, Name: (2-Methyl-1H-imidazol-4-yl)methanol.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Arimoto, Masahiro published the artcileSemisynthetic β-lactam antibiotics. IV. Synthesis and antibacterial activity of 7β-[2-(hetero aromatic methoxyimino)-2-(2-aminothiazol-4-yl)acetamido]cephalosporins, Product Details of C5H8N2O, the publication is Journal of Antibiotics (1988), 41(12), 1795-811, database is CAplus and MEDLINE.

Title compounds I [R = OAc, 1-methyl-5-tetrazolylthio, (un)substituted pyridinium, 1-methylpyrrolidinium, pyridazinium; R¹ = (un)substituted imidazol-4-yl, 1,2,3-triazol-4-yl, pyridazin-3-yl, pyrimidin-4-yl, pyrazinyl] were synthesized and bacteriol. evaluated. Several I showed exceptional in vitro activity. The most active derivative, I (R = pyridinium, R¹ = imidazol-4-yl), was the most evenly balanced with respect to activity against Gram-pos. and Gran-neg. bacteria. Furthermore, I (R = pyridinium, R¹ = imidazol-4-yl) was stable to various types of β-lactamases and had high affinities for penicillin binding protein-3 and -1Bs of both Escherichia coli and Pseudomonas aeruginosa.

Journal of Antibiotics published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C5H8N2O, Product Details of C5H8N2O.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Fujiwara, Tomoyuki published the artcilePigment formation by ultraviolet-ray decomposition of histidine, Recommanded Product: (2-Methyl-1H-imidazol-4-yl)methanol, the publication is Nagasaki Igakkai Zasshi (1954), 726-30, database is CAplus.

Histidine (I), histamine, imidazoleacetic acid, 4(5)-hydroxymethylimidazole, and 2-methyl-4(5)-hydroxymethyl-imidazole (II) (2 mg. of each compound in 5 ml. of 4% Na₂-CO₃ solution) were irradiated for 2 hrs. by ultraviolet rays. All except II gave rise to pigment. When I is irradiated, a compound which reacts with Folin-Ciocalteu reagent is formed. Thus, pigment appears to be a polymerized 2-hydroxyimidazole.

Nagasaki Igakkai Zasshi published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C5H8N2O, Recommanded Product: (2-Methyl-1H-imidazol-4-yl)methanol.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Suter, Scott R. published the artcileStructure-Guided Control of siRNA Off-Target Effects, Recommanded Product: (2-Methyl-1H-imidazol-4-yl)methanol, the publication is Journal of the American Chemical Society (2016), 138(28), 8667-8669, database is CAplus and MEDLINE.

Short interfering RNAs (siRNAs) are promising therapeutics that make use of the RNA interference (RNAi) pathway, but liabilities arising from the native RNA structure necessitate chem. modification for drug development. Advances in the structural characterization of components of the human RNAi pathway have enabled structure-guided optimization of siRNA properties. Here the authors report the 2.3 Å resolution crystal structure of human Argonaute 2 (hAgo2), a key nuclease in the RNAi pathway, bound to an siRNA guide strand bearing an unnatural triazolyl nucleotide at position 1 (g1). Unlike natural nucleotides, this analog inserts deeply into hAgo2’s central RNA binding cleft and thus is able to modulate pairing between guide and target RNAs. The affinity of the hAgo2-siRNA complex for a seed-only matched target was significantly reduced by the triazolyl modification, while the affinity for a fully matched target was unchanged. In addition, siRNA potency for off-target repression was reduced (4-fold increase in IC₅₀) by the modification, while on-target knockdown was improved (2-fold reduction in IC₅₀). Controlling siRNA on-target vs. microRNA (miRNA)-like off-target potency by projection of substituent groups into the hAgo2 central cleft from g1 is a new approach to enhance siRNA selectivity with a strong structural rationale.

Journal of the American Chemical Society published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C4H7BrO, Recommanded Product: (2-Methyl-1H-imidazol-4-yl)methanol.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Gortinskaya, T. V. published the artcileSome derivatives of 4,4′-dihydrazinodiphenyl sulfone and 4-hydrazinophenyl 2-acetamido-5-thiazolyl sulfone, SDS of cas: 45533-87-7, the publication is Zhurnal Obshchei Khimii (1957), 1960-4, database is CAplus.

Heating 1.4 g. opianic acid in 50 ml. EtOH with 1 g. (p-HCl.H₂NNHC₆H₄)₂SO₂ in 10 ml. H₂O gave a precipitate of 2.2 g. {4-[2,3,4-HO₂C(MeO)₂C₆H₂CH:NNH]C₆H₄}₂SO₂ (I), m. 268-9°. If the reaction is run in H₂O there is formed yellow II, m. 258-60°, which changes to I on heating with ROH or alc. H₂SO₄. Hydrogenation of 4-nitrophenyl-2-amino-5-thiazolyl sulfone in EtOH over Raney Ni gave 87% 4-H₂NC₆H₄ analog, m. 217-19°. Hydrogenation of 4-nitrophenyl-2-acetamido-5-thiazolyl sulfone over Raney Ni in H₂O gave the 4-H₂NC₆H₄ analog, m. 268-9°. This (5.4 g.), 42 ml. AcOH, 21 ml. concentrated HCl, and 10.5 ml. H₂O diazotized with 1.1 g. NaNO₂ at 0° and the solution treated with 7.85 g. SnCl₂ in 38.5 ml. HCl, and kept 2 days at room temperature gave 0.3 g. p-H₂NNHC₆H₄ analog HCl salt, m. 222°; the filtrate treated with H₂S and filtered gave with NH₄OH 1.6 g. free base (IIA), m. 243-5°. The following hydrazones are reported: from (p-H₂NNHC₆H₄)₂SO₂ (III) and p-HOC₆H₄CHO, m. 238-40°; from III and p-AcNHC₆H₄CHO, m. 262-5°; from III and 3,4-MeO(HO)C₆H₃CHO, m. 250-2°; from 4-hydrazinophenyl-2-acetamido-5-thiazolyl sulfone (IV) and p-AcNHC₆H₄CHO, m. 221-3°; from IV and 3,4-MeO(HO)C₆H₃CHO, m. 238-40°; from IV and opianic acid, m. 263-4°. III showed some in vitro activity against human and avian tuberculosis and acid-fast saprophytic sp., Microsporon sp., Trichophyton sp., Achorion sp., and actinomyces sp. Some activity was found for III hydrazone, p-HOC₆H₄CHO, and IIA.

Zhurnal Obshchei Khimii published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C5H8N2O, SDS of cas: 45533-87-7.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Sitzius, Hannelore published the artcileMass spectrometric studies of 4(5)-hydroxymethylimidazoles, Application In Synthesis of 45533-87-7, the publication is Archiv der Pharmazie (Weinheim, Germany) (1979), 312(12), 994-1003, database is CAplus.

The mass spectra of 11 I (R, R¹ = H, Me; R² = H, Me, cyclohexyl, p-tolyl, PhCH₂CH₂, Et, Pr) and of II are described and schemes for the fragmentation of I (R = R¹ = R² = H) and II are given.

Archiv der Pharmazie (Weinheim, Germany) published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C10H12F6N4O6PdS2, Application In Synthesis of 45533-87-7.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Madsen, Christian published the artcile5-Substituted Imidazole-4-acetic Acid Analogues: Synthesis, Modeling, and Pharmacological Characterization of a Series of Novel γ-Aminobutyric Acid_C Receptor Agonists, Synthetic Route of 45533-87-7, the publication is Journal of Medicinal Chemistry (2007), 50(17), 4147-4161, database is CAplus and MEDLINE.

A series of ring-substituted analogs of imidazole-4-acetic acid (IAA), a partial agonist at both GABA_A and GABA_C receptors (GABA = γ-aminobutyric acid), have been synthesized. The synthesized compounds, e.g. I·HCl, have been evaluated as ligands for the α₁β₂γ_2S GABA_A receptors and the ρ₁ GABA_C receptors using the FLIPR membrane potential (FMP) assay and by electrophysiol. techniques. None of the tested compounds displayed activity at the GABA_A receptors at concentrations up to 1000 μM. However, the 5-Me, 5-Ph, 5-p-Me-Ph, and 5-p-F-Ph IAA analogs, displayed full agonist activities at the ρ₁ receptors in the FMP assay (EC₅₀ in the range 22-420 μM). Ligand-protein docking identified the Thr129 in the α₁ subunit and the corresponding Ser168 residue in ρ₁ as determinants of the selectivity displayed by the 5-substituted IAA analogs. The fact that GABA, IAA, and I·HCl displayed decreased agonist potencies at a ρ₁Ser168Thr mutant compared to the WT ρ₁ receptor strongly supported this hypothesis. However, in contrast to GABA and IAA, which exhibited increased agonist potencies at a α₁(Thr129Ser)β₂γ₂ mutant compared to WT GABA_A receptor, the data obtained for I·HCl at the WT and mutant receptors were nonconclusive.

Journal of Medicinal Chemistry published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C5H8N2O, Synthetic Route of 45533-87-7.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Gerlinger, Erich published the artcileMechanistic studies of the urocanase reaction using proton and phosphorus-31 NMR spectroscopy and the substrate analog 2-methylurocanate, Category: imidazoles-derivatives, the publication is Tetrahedron (1983), 39(21), 3523-8, database is CAplus.

The reaction of 2-methylurocanate with urocanase from Pseudomonas putida was monitored by ¹H NMR spectroscopy at 500 MHz. 2-Methylurocanate reacted 128-fold more slowly with urocanase than did urocanate. No signals for the enol form of the 2-methylimidazolone propionate produced were detected. 2-Methylimidazolone propionate was ∼25-fold more stable to hydrolysis than imidazolone propionate. The urocanase-catalyzed exchange of the 5-H of 2-methylurocanate with the solvent ²H was 1.3-fold faster than the overall reaction. The nonenzymic exchange of the Me protons of 2-methylimidazolone propionate with solvent ²H took place with a half-life of 5.8 h. ¹H NMR spectroscopy showed that the urocanase reaction is reversible. At 8° and pD 6.3, 1.6% of the total imidazolone propionate was converted into urocanate. Apart from the pyrophosphate ester group of NAD, no phosphorylated groups were detected in urocanase by ³¹P NMR spectroscopy.

Tetrahedron published new progress about 45533-87-7. 45533-87-7 belongs to imidazoles-derivatives, auxiliary class Imidazole,Alcohol,Imidazole, name is (2-Methyl-1H-imidazol-4-yl)methanol, and the molecular formula is C5H8N2O, Category: imidazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem