Category: imidazoles-derivatives

Sosnowski, Jerzy published the artcilePreparation of prolonged-release tablets with antazoline hydrochloride by the mixed granulate method and double-layer tablets, Synthetic Route of 2508-72-7, the publication is Farmacja Polska (1986), 42(11), 611-15, database is CAplus.

One of the granulates used and one of the layers in the resulting tablets contained a hydrophobic matrix comprising poly(vinyl chloride). Two doses of the active substance were used as well as various excipients and various proportions of distribution of the active substance between the particular granulates or layers. The rate of in vitro release of antazoline-HCl from these tablets was estimated by the half-exchange method into artificial gastric and intestinal juices.

Farmacja Polska published new progress about 2508-72-7. 2508-72-7 belongs to imidazoles-derivatives, auxiliary class Inhibitor,Immunology/Inflammation,Histamine Receptor, name is N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, and the molecular formula is C7H8BClO2, Synthetic Route of 2508-72-7.

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

Sosnowski, Jerzy published the artcileElaboration of a preparation method of matrix tablets containing antazoline hydrochloride, HPLC of Formula: 2508-72-7, the publication is Farmacja Polska (1986), 42(8), 409-11, database is CAplus.

The matrix comprised poly(vinyl chloride), Et cellulose or Eudragit RL PM. Antazoline-HCl (I) was incorporated in the matrix by wet granulation. A solution of 10% Et cellulose in anhydrous EtOH, aqueous 4% solution of gelatin or 96% EtOH were used as binders. The in vitro release rate of I from these tablets was estimated by the half-exchange method.

Farmacja Polska published new progress about 2508-72-7. 2508-72-7 belongs to imidazoles-derivatives, auxiliary class Inhibitor,Immunology/Inflammation,Histamine Receptor, name is N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, and the molecular formula is C18H23OP, HPLC of Formula: 2508-72-7.

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

Boulebd, Houssem published the artcileSynthesis and biological evaluation of heterocyclic privileged medicinal structures containing (benz)imidazole unit, HPLC of Formula: 7467-35-8, the publication is Monatshefte fuer Chemie (2016), 147(12), 2209-2220, database is CAplus.

Abstract: New heterocyclic privileged medicinal scaffolds involving 4H-pyran, 1,4-dihydropyridine, quinazoline, and 2-aminochromene bearing a (benz)imidazole unit were prepared in good to excellent yields, and evaluated for their in vitro hepatotoxicity on HepG2 cells and antioxidant activity using DPPH radical-scavenging assay. From these results, 2-amino-4-(1-methyl-1H-imidazol-2-yl)-4H-benzo[h]chromene-3-carbonitrile has been identified as a racemic, readily available imidazole derivative, significantly less hepatotoxic than tacrine at 100 μM concentration One compound was a potent antioxidant agent. The catalytic effect of the 1-methylimidazole unit, in the synthesis of some heterocycle, was also demonstrated. Crystal x-ray structures are reported for six compounds Graphical abstract: [Figure not available: see fulltext.].

Monatshefte fuer Chemie published new progress about 7467-35-8. 7467-35-8 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Alcohol, name is (1-Methyl-1H-benzo[d]imidazol-2-yl)methanol, and the molecular formula is C9H10N2O, HPLC of Formula: 7467-35-8.

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

Chuh, Kelly N. published the artcileChanges in Metabolic Chemical Reporter Structure Yield a Selective Probe of O-GlcNAc Modification, SDS of cas: 359860-27-8, the publication is Journal of the American Chemical Society (2014), 136(35), 12283-12295, database is CAplus and MEDLINE.

Metabolic chem. reporters (MCRs) of glycosylation are analogs of monosaccharides that contain bioorthogonal functionalities and enable the direct visualization and identification of glycoproteins from living cells. Each MCR was initially thought to report on specific types of glycosylation. The authors and others demonstrated that several MCRs are metabolically transformed and enter multiple glycosylation pathways. Therefore, the development of selective MCRs remains a key unmet goal. The authors demonstrate here that 6-azido-6-deoxy-N-acetyl-glucosamine (6AzGlcNAc) is a specific MCR for O-GlcNAcylated proteins. Biochem. anal. and comparative proteomics with 6AzGlcNAc, N-azidoacetyl-glucosamine (GlcNAz), and N-azidoacetyl-galactosamine (GalNAz) revealed that 6AzGlcNAc exclusively labels intracellular proteins, while GlcNAz and GalNAz are incorporated into a combination of intracellular and extracellular/lumenal glycoproteins. Notably, 6AzGlcNAc cannot be biosynthetically transformed into the corresponding UDP sugar-donor by the canonical salvage-pathway that requires phosphorylation at the 6-hydroxyl. In vitro experiments showed that 6AzGlcNAc can bypass this roadblock through direct phosphorylation of its 1-hydroxyl by the enzyme phosphoacetylglucosamine mutase (AGM1). Taken together, 6AzGlcNAc enables the specific anal. of O-GlcNAcylated proteins, and these results suggest that specific MCRs for other types of glycosylation can be developed. Addnl., the authors’ data demonstrate that cells are equipped with a somewhat unappreciated metabolic flexibility with important implications for the biosynthesis of natural and unnatural carbohydrates.

Journal of the American Chemical Society published new progress about 359860-27-8. 359860-27-8 belongs to imidazoles-derivatives, auxiliary class Other Aliphatic Heterocyclic,Chiral,Amine,Amide,Ether,Inhibitor, name is N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, and the molecular formula is C18H34N4O5S, SDS of cas: 359860-27-8.

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

Taldone, Tony published the artcileDesign, synthesis, and evaluation of small molecule Hsp90 probes, Related Products of imidazoles-derivatives, the publication is Bioorganic & Medicinal Chemistry (2011), 19(8), 2603-2614, database is CAplus and MEDLINE.

A number of compounds from different chem. classes are known to bind competitively to the ATP-pocket of Hsp90 and inhibit its chaperone function. The natural product geldanamycin was the first reported inhibitor of Hsp90 and since then synthetic inhibitors from purine, isoxazole and indazol-4-one chem. classes have been discovered and are currently or soon to be in clin. trials for the treatment of cancer. In spite of a similar binding mode to Hsp90, distinct biol. profiles were demonstrated among these mols., both in vitro and in vivo. To better understand the mol. basis for these dissimilarities, we report here the synthesis of chem. tools for three Hsp90 inhibitor classes. These agents will be useful for probing tumor-by-tumor the Hsp90 complexes isolated by specific inhibitors. Such information will lead to better understanding of tumor specific mol. markers to aid in their clin. development. It will also help to elucidate the mol. basis for the biol. differences observed among Hsp90 inhibitors.

Bioorganic & Medicinal Chemistry published new progress about 359860-27-8. 359860-27-8 belongs to imidazoles-derivatives, auxiliary class Other Aliphatic Heterocyclic,Chiral,Amine,Amide,Ether,Inhibitor, name is N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, and the molecular formula is C11H24O3, Related Products of imidazoles-derivatives.

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

Li, Dan published the artcileQuality control of esomeprazole sodium enteric-coated tablets, Recommanded Product: Sodium (S)-6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide, the publication is Yiyao Daobao (2013), 32(5), 683-685, database is CAplus.

Quality control method for esomeprazole sodium enteric-coated tablets was established. Content of esomeprazole was determined by HPLC, and enantiomer of esomeprazole was identified by normal phase chromatog.

Yiyao Daobao published new progress about 161796-78-7. 161796-78-7 belongs to imidazoles-derivatives, auxiliary class Membrane Transporter/Ion Channel,Proton Pump, name is Sodium (S)-6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide, and the molecular formula is C17H18N3NaO3S, Recommanded Product: Sodium (S)-6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide.

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

Bai, Yu-Bin published the artcileSynthesis and Antifungal Activity of 2-Chloromethyl-1H-benzimidazole Derivatives against Phytopathogenic Fungi in Vitro, Category: imidazoles-derivatives, the publication is Journal of Agricultural and Food Chemistry (2013), 61(11), 2789-2795, database is CAplus and MEDLINE.

A series of 35 benzimidazole derivatives were synthesized from 2-chloromethyl-1H-benzimidazole in good yields. Their structures were characterized by ¹H and ¹³C NMR and HRESIMS. Antifungal activities of all of the synthesized compounds were evaluated against five phytopathogens fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani, and Fusarium solani) using the mycelium growth rate method. Compound 1-methyl-2-(phenoxymethyl)-1H-benzo[d]imidazole (4m) displayed strong growth inhibition of C. gloeosporioides, A. solani, and F. solani with IC₅₀ of 20.76, 27.58, and 18.60 μg/mL, resp. Selective inhibition of B. cinerea instead of the other fungal pathogenes was observed with 2-[(4-Chlorophenoxy)methyl]-1-methyl-5-nitro-1H-benzo[d]imidazole (7f) (IC₅₀ of 13.36 μg/mL), comparable to that of pos. control, a com. agricultural fungicide hymexazol (IC₅₀ of 8.92 μg/mL). Compound 2-(chloromethyl)-1-(methylsulfonyl)-1H-benzo[d]imidazole (5b) exhibited remarkable antifungal properties against Cytospora sp., C. gloeosporioides, B. cinerea, and F. solani with IC₅₀ values of 30.97, 11.38, 57.71, and 40.15 μg/mL, resp.; among the target fungi, 5b was the most active compound and superior to the reference against C. gloeosporioides alone. Structure-activity relationship (SAR) data of these compounds are as follows: (1) introduction of the chlorine atom on para-position in the benzene ring help to increase activity (2-((4-chlorophenoxy)methyl)-1-methyl-1H-benzo[d]imidazole (4f) vs. 1-[4-[(1-Methyl-1H-benzo[d]imidazol-2-yl)methoxy]phenyl]ethanone (4c); 2-[(4-Chlorophenoxy)methyl]-1-methyl-5-nitro-1H-benzo[d]imidazole (7f) vs. 2-[(Benzo[d][1,3]dioxol-5-yloxy)methyl]-1-methyl-5-nitro-1H-benzo[d]imidazole (7n)), (2) the sulfonyl group is critical for the inhibition of C. gloeosporioides (5b and 2-(Chloromethyl)-1-[(4-chlorophenyl)sulfonyl]-1H-benzo[d]imidazol (5c) vs. 1-(2-(chloromethyl)-1H-benzo[d]imidazol-1-yl)ethanone (5a)), and (3) the unsubstituted benzene ring improve activity (4m vs. 2-[(Benzo[d][1,3]dioxol-5-yloxy)methyl]-1-methyl-1H-benzo[d]imidazole (4n), 2-((4-fluorophenoxy)methyl)-1-methyl-1H-benzo[d]imidazole (4e) and 1-[3-[(1-Methyl-1H-benzo[d]imidazol-2-yl)methoxy]phenyl]ethanone (4a)). Thus, compounds 5b, 4m, and 7f emerged as a new leading structure for the development of new fungicides.

Journal of Agricultural and Food Chemistry published new progress about 4760-35-4. 4760-35-4 belongs to imidazoles-derivatives, auxiliary class Chloride,Benzimidazole, name is 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, and the molecular formula is C9H9ClN2, Category: imidazoles-derivatives.

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

Weng, Yangyang published the artcileNickel-catalyzed allylic carbonylative coupling of alkyl zinc reagents with tert-butyl isocyanide, Recommanded Product: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Nature Communications (2020), 11(1), 392, database is CAplus and MEDLINE.

By leveraging easily accessible tert-Bu isocyanide as the CO surrogate, a nickel-catalyzed allylic carbonylative coupling with alkyl zinc reagent RZnX (R = Me, n-Bu, Bn, cyclopentyl, 2-chloropyridin-5-yl, etc.; X = Br, Cl), allowing for the practical and straightforward preparation of synthetically important β,γ-unsaturated ketones R¹CH=C(R²)CH(R³)C(O)R (R¹ = n-Pr, Ph, cyclohexyl, furan-2-yl, etc.; R² = H, Me; R³ = H, Me, Et, cyclopropyl) in a linear-selective fashion with excellent trans-selectivity under mild conditions was described. Moreover, the undesired polycarbonylation process which is often encountered in palladium chem. could be completely suppressed. This nickel-based method features excellent functional group tolerance, even including the active aryl iodide functionality to allow the orthogonal derivatization of β,γ-unsaturated ketones. Preliminary mechanistic studies suggest that the reaction proceeds via π-allylnickel intermediate.

Nature Communications published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C12H14O2, Recommanded Product: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride.

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

Yang, Ze-Kun published the artcileCross-coupling polycondensation via C-O or C-N bond cleavage, Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Nature Communications (2018), 9(1), 1-7, database is CAplus and MEDLINE.

π-Conjugated polymers are widely used in optoelectronics for fabrication of organic photovoltaic devices, organic light-emitting diodes, organic field effect transistors, and so on. Here we describe the protocol for polycondensation of bifunctional aryl ethers or aryl ammonium salts with aromatic dimetallic compounds through cleavage of inert C-O/C-N bonds. This reaction proceeds smoothly in the presence of com. available Ni/Pd catalyst under mild conditions, affording the corresponding π-conjugated polymers with high mol. weight The method is applicable to monomers that are unreactive in other currently employed polymerization procedures, and opens up the possibility of transforming a range of naturally abundant chems. into useful functional compounds/polymers.

Nature Communications published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C11H21BF4N2O2, Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride.

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

Li, Jiang-Fei published the artcileConstruction 7-membered ring via Ni-Al bimetal-enabled C-H cyclization for synthesis of tricyclic imidazoles, Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Nature Communications (2021), 12(1), 3070, database is CAplus and MEDLINE.

A direct construction of 7-membered rings via Ni-Al co-catalyzed unreactive C7-H cyclization of benzoimidazoles with alkenes, providing a series of tricyclic imidazoles such as I [R = Me, 2-FC₆H₄, BnO(CH₂)₂, etc.; R¹ = CF₃, 3-pyridyl, Bn, etc.; R² = H, 4-t-Bu, 4,5-F₂, etc.] in 40-98% yield and with up to 95:5 er was reported.

Nature Communications published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C27H39ClN2, Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride.

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