Month: December 2022

Huang, Shuai published the artcilePd-Catalyzed umpolung asymmetric allylic alkylation of hydrazones to vicinal tertiary and quaternary chiral carbon centers, Quality Control of 258278-25-0, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(21), 3513-3516, database is CAplus and MEDLINE.

Diastereo- and enantioselective construction of vicinal tertiary and quaternary carbon centers is a great challenge in synthetic chem. Herein, a facile and efficient protocol to construct unsaturated azo compounds I [R¹ = Ph, 4-FC₆H₄, 2-naphthyl, 2-thienyl, etc., R² = Me; R¹ = Ph, R² = Et; R¹R² = (CH₂)₅; R³ = Ph, 4-MeOC₆H₄, 1,3-benzodioxol-5-yl, 2-furyl, etc.] with vicinal tertiary and quaternary chiral carbon centers in high yields with high regio-, diastereo- and enantioselectivities via Pd-catalyzed umpolung asym. allylic alkylation of hydrazones II with monosubstituted allylic pivalates R³CH:CHCH₂OC(O)Bu-t by using Kundig-type chiral N-heterocyclic carbene as the ligand is reported. The control experiments revealed that the reaction proceeds via the inner-sphere mechanism.

Chemical Communications (Cambridge, United Kingdom) 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, Quality Control of 258278-25-0.

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

Lin, Jian-Ping published the artcileSolvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines, SDS of cas: 2622-67-5, the publication is Organic Letters (2014), 16(11), 2822-2825, database is CAplus and MEDLINE.

A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp³)-C(sp²) and C(sp²)-N bond formation in nonpolar and polar solvents, resp. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp³C-H/sp²C-H direct coupling of the amidine with K₂S₂O₈ as the oxidant. No metal, base, or other additives were needed.

Organic Letters published new progress about 2622-67-5. 2622-67-5 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Benzene,Benzimidazole, name is 1,2-Diphenyl-1H-benzo[d]imidazole, and the molecular formula is C19H14N2, SDS of cas: 2622-67-5.

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

Han, Liangliang published the artcileEfficiency phosphorescent OLEDs with a low roll-off based on a hetero-triplet iridium complex, Safety of 1,2-Diphenyl-1H-benzo[d]imidazole, the publication is Dyes and Pigments (2015), 649-654, database is CAplus.

To explore the triplet-triplet annihilation in cyclometalated Ir complexes, a hetero-triplet Ir complex [Ir(ppy)₂pbi] employing 2 2-phenylpyridine (Hppy) ligands and one 1,2-diphenyl-1H-benzo[d]imidazole (Hpbi) ligand with similar triplet energies was synthesized. A device based on Ir(ppy)₂pbi exhibited high current efficiency 26.7 cd/A at high doping concentration 12%. The current efficiency was still maintained at 25.8 cd/A when the c.d. was >253.2 mA/cm². The efficiency roll-off was only ∼3.4%, much lower than that of traditional cyclometalated Ir complexes. Probably the complicated energy level and unsym. ligand in Ir(ppy)₂pbi may help to suppress the triplet-triplet annihilation.

Dyes and Pigments published new progress about 2622-67-5. 2622-67-5 belongs to imidazoles-derivatives, auxiliary class Benzimidazole,Benzene,Benzimidazole, name is 1,2-Diphenyl-1H-benzo[d]imidazole, and the molecular formula is C19H14N2, Safety of 1,2-Diphenyl-1H-benzo[d]imidazole.

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

Tan, Shuai published the artcileTuning the Charge and Hydrophobicity of Graphene Oxide Membranes by Functionalization with Ionic Liquids at Epoxide Sites, Quality Control of 79917-90-1, the publication is ACS Applied Materials & Interfaces (2022), 14(16), 19031-19042, database is CAplus and MEDLINE.

Functionalization of graphene oxide (GO) membranes is generally achieved using carboxyl groups as binding sites for ligands. Herein, by taking advantage of the ability of imidazolium-based ionic liquids (ILs) to undergo an epoxide ring-opening reaction, a new approach of GO modification was established, in which ILs were bonded to the abundant epoxides on GO without sacrificing the carboxyl groups. Computational methods confirmed this unique configuration of ILs on GO, which enabled the dispersion of IL/GO flakes in water for facile casting into laminate membranes. Compared with neat GO, the ILs in IL/GO membranes served as spacers that substantially reduced the multi-valent cation mobility, simultaneously facilitated ion desolvation, and increased the water flux across the membrane. Our studies found that the higher separation efficiency of IL/GO membranes may be attributed to the synergistic modification of the hydrophobicity and surface charge. Specifically, the protonated nitrogen of the imidazolium cations altered the surface charge of GO, thereby generating electrostatic repulsion that enhanced the selectivity of cation rejection. On the other hand, the increased length of the alkyl chains bound to the imidazolium rings was found to increase the hydrophobicity of GO, which, in turn, aided the fine-tuning of the water desolvation/transport dynamics at the GO/IL interface to achieve a high water flux. Addnl., the water retention was reduced on the hydrophobic planes, which inhibited GO swelling during aqueous separations Mol. dynamics simulations revealed increased water diffusivity when ILs were intercalated within GO layers. We establish that without requiring a high energy input, functionalization of GO membranes with ILs may be a promising approach to achieve efficient ion separation and critical material recovery.

ACS Applied Materials & Interfaces published new progress about 79917-90-1. 79917-90-1 belongs to imidazoles-derivatives, auxiliary class Ionic Liquid,Ionic Liquid, name is 3-Butyl-1-methyl-1H-imidazol-3-ium chloride, and the molecular formula is C8H11BO2, Quality Control of 79917-90-1.

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

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

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

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

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

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