Imidazoles-derivatives

Gu, Yang published the artcileLigand-Controlled Copper-Catalyzed Highly Regioselective Difluoromethylation of Allylic Chlorides/Bromides and Propargyl Bromides, Product Details of C27H39ClN2, the publication is Chinese Journal of Chemistry (2018), 36(1), 55-58, database is CAplus.

Highly regiodivergent copper-catalyzed allylic/propargylic difluoromethylation reactions by employing different ligands were described. When 5,6-dimethyl-1,10-phenanthroline was used as the ligand, exclusively α-difluoromethylated products I [R = 4-ClC₆H₄, 4-CF₃C₆H₄, 1-naphthyl, etc.] were obtained, while γ-selective difluoromethylated products II were generated when N-heterocyclic carbene-SIPr was used as the ligand. Likewise, α-difluoromethylated products III [Ar = 4-ClC₆H₄, 4-CF₃C₆H₄, 4-t-BuC₆H₄, etc.] and γ-difluoromethylated products IV were achieved in the presence of similar copper catalysts for the reactions of propargyl bromides. Moreover, a copper-catalyzed asym. allylic difluoromethylation reaction with moderate to good enantioselectivity by the use of chiral ligands was afforded α-difluoromethylated products II [R = 3-ClC₆H₄, 4-CO₂MeC₆H₄, 2,5-(Br)₂C₆H₃, etc.].

Chinese Journal of Chemistry 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, Product Details of C27H39ClN2.

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

Li, Youshan published the artcileBioorthogonal Ligation and Cleavage by Reactions of Chloroquinoxalines with ortho-Dithiophenols, Category: imidazoles-derivatives, the publication is Angewandte Chemie, International Edition (2020), 59(9), 3671-3677, database is CAplus and MEDLINE.

A bioorthogonal ligation and cleavage method via reactions of chloroquinoxalines (CQ) and ortho-dithiophenols (DT) is presented. Double nucleophilic substitutions of ortho-dithiophenols to chloroquinoxalines provide conjugates containing tetracyclic benzo[5,6][1,4]dithiino[2,3-b]quinoxaline with strong built-in fluorescence together with release of the other functional mols. Three cleavable linkers were designed and successfully used in release of the mols. containing biotin from the protein conjugates. The CQ-DT bioorthogonal reactions can be applied for the bioorthogonal ligations, bioorthogonal cleavages, and trans-tagging of proteins, and show advantages of readily accessible unnatural orthogonal groups, appealing reaction kinetics (k₂ â‰?1.3 m^-1 s^-1), excellent biocompatibility of orthogonal groups, and high stability of conjugates. This complements previous bioorthogonal reactions and is a new route for protein-fishing applications and in-gel fluorescence anal.

Angewandte Chemie, International Edition 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, Category: imidazoles-derivatives.

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

Sioriki, Eleni published the artcileIn vitro Anti-atherogenic Properties of N-Heterocyclic Carbene Aurate(I) Compounds, Product Details of C27H39ClN2, the publication is ChemMedChem (2018), 13(23), 2484-2487, database is CAplus and MEDLINE.

The anti-atherogenic (anti-inflammatory) properties of various aurate(I) salts, of the general formula [NHC·H][AuCl₂] (NHC=N-heterocyclic carbene) were investigated. The aurates were easily synthesized and obtained in anal. pure form. In addition, the biol. activity of these compounds against atheromatosis via in vitro inhibition of platelet-activating factor (PAF)-induced platelet aggregation was probed. All complexes were found to possess anti-aggregatory properties in vitro with [IPr*·H][AuCl₂] (6) being the most potent inhibitor of PAF at micromolar concentration Based on our findings, we conclude that these simply assembled aurates are a very promising class of PAF inhibitors and anti-inflammatory drugs.

ChemMedChem 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 C9H13NO2, Product Details of C27H39ClN2.

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

Menendez, Guillermo O. published the artcileA Versatile Near-Infrared Asymmetric Tricarbocyanine for Zinc Ion Sensing in Water, Recommanded Product: N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide, the publication is Photochemistry and Photobiology (2013), 89(6), 1354-1361, database is CAplus and MEDLINE.

We have synthesized a near-IR emissive asym. tricarbocyanine conveniently functionalized to improve bioconjugation. The leading structure contains a versatile derivatization point at the meso position for facile radical-nucleophilic aromatic substitution. We have evaluated a DPEN (N,N-di(2-picolyl)ethylendiamine) derivative of this dye as a highly selective sensor for zinc (II) in aqueous medium, which performs in an appropriate sensitivity range for biol. studies. The probe was successfully conjugated to a protein-ligand model with high affinity and specificity (biotin-streptavidin technol.) rendering an excellent performance of sensing. In a general strategy to obtain sensitive probes combining fluorescent nanoparticles and mol. fluorophores, a preliminary design of a supramol. assembly derived from the conjugation of the mol. sensor to quantum dots (QDs) was also investigated. The advantages and problems of FRET-based sensors are also discussed.

Photochemistry and Photobiology 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, Recommanded Product: N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide.

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

Mitra, Mainak published the artcileEvidence that steric factors modulate reactivity of tautomeric iron-oxo species in stereospecific alkane C-H hydroxylation, HPLC of Formula: 4760-35-4, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(12), 1408-1410, database is CAplus and MEDLINE.

A new iron complex mediates stereospecific hydroxylation of alkyl C-H bonds with hydrogen peroxide, exhibiting excellent efficiency. Isotope labeling studies provide evidence that the relative reactivity of tautomerically related oxo-iron species responsible for the C-H hydroxylation reaction is dominated by steric factors.

Chemical Communications (Cambridge, United Kingdom) 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, HPLC of Formula: 4760-35-4.

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

Han, Yali published the artcileHalf-sandwich Iridium(III) Benzimidazole-Appended Imidazolium-Based N-heterocyclic Carbene Complexes and Antitumor Application, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole, the publication is Chemistry – An Asian Journal (2018), 13(23), 3697-3705, database is CAplus and MEDLINE.

A series of half-sandwich iridium(III) benzimidazole-appended imidazolium-based N-heterocyclic carbene (NHC) antitumor complexes [(η⁵-Cp^x)Ir(CN̂)Cl]Cl, where Cp^x is pentamethylcyclopentadienyl (Cp*) or its biphenyl derivative (Cp^xbiph) and CN̂ is a NHC chelating ligand, were successfully synthesized and characterized. The Ir^III complexes showed potential antitumor activity against A549 cells, at most three times more potent than cis-platin under the same conditions. Complexes could bind to BSA by a static quenching mode, catalyzing the change of NADH to NAD⁺ and inducing the production of reactive oxygen species (maximum turnover number, 9.8), which play an important role in regulating cell apoptosis. Confocal microscopy showed that the complexes could specifically target lysosomes in cells with a Pearson’s co-localization coefficient 0.76 and 0.72 after 1 h and 6 h, resp., followed an energy-dependent cellular uptake mechanism and damaged the integrity of lysosomes. At the same time, complexes caused a marked loss of mitochondrial membrane potential.

Chemistry – An Asian Journal 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, Recommanded Product: 2-(Chloromethyl)-1-methyl-1H-benzo[d]imidazole.

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

Liu, Zhen-zhen published the artcileIdentification of pimavanserin tartrate as a potent Ca²⁺-calcineurin-NFAT pathway inhibitor for glioblastoma therapy, Recommanded Product: N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride, the publication is Acta Pharmacologica Sinica (2021), 42(11), 1860-1874, database is CAplus and MEDLINE.

Glioblastoma multiforme (GBM) is the most common and malignant type of primary brain tumor, and 95% of patients die within 2 years after diagnosis. In this study, aiming to overcome chemoresistance to the first-line drug temozolomide (TMZ), we carried out research to discover a novel alternative drug targeting the oncogenic NFAT signaling pathway for GBM therapy. To accelerate the drug′s clin. application, we took advantage of a drug repurposing strategy to identify novel NFAT signaling pathway inhibitors. After screening a set of 93 FDA-approved drugs with simple structures, we identified pimavanserin tartrate (PIM), an effective 5-HT_2A receptor inverse agonist used for the treatment of Parkinson′s disease-associated psychiatric symptoms, as having the most potent inhibitory activity against the NFAT signaling pathway. Further study revealed that PIM suppressed STIM1 puncta formation to inhibit store-operated calcium entry (SOCE) and subsequent NFAT activity. In cellula, PIM significantly suppressed the proliferation, migration, division, and motility of U87 glioblastoma cells, induced G1/S phase arrest and promoted apoptosis. In vivo, the growth of s.c. and orthotopic glioblastoma xenografts was markedly suppressed by PIM. Unbiased omics studies revealed the novel mol. mechanism of PIM′s antitumor activity, which included suppression of the ATR/CDK2/E2F axis, MYC, and AuroraA/B signaling. Interestingly, the genes upregulated by PIM were largely associated with cholesterol homeostasis, which may contribute to PIM′s side effects and should be given more attention. Our study identified store-operated calcium channels as novel targets of PIM and was the first to systematically highlight the therapeutic potential of pimavanserin tartrate for glioblastoma.

Acta Pharmacologica Sinica 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 C17H20ClN3, Recommanded Product: N-Benzyl-N-((4,5-dihydro-1H-imidazol-2-yl)methyl)aniline hydrochloride.

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

Paresi, Chelsea J. published the artcileBenzimidazole covalent probes and the gastric H⁺/K⁺-ATPase as a model system for protein labeling in a copper-free setting, Application In Synthesis of 359860-27-8, the publication is Molecular BioSystems (2016), 12(6), 1772-1780, database is CAplus and MEDLINE.

Affinity probes are useful tools for determining mol. targets and elucidating mechanism of action for novel, bioactive compounds In the case of covalent inhibitors, activity based probes are particularly valuable for ensuring acceptable selectivity margins. However, there is a variety of bioorthogonal chem. reactions available for modifying compounds of interest with clickable tags. Here, we describe a direct comparison of tetrazine ligation and strain promoted azide-alkyne cycloaddition using benzimidazole based probes to bind their known target, the gastric proton pump, ATP4A. This study validates the use of chem. probes for target identification and illustrates the superior efficiency of tetrazine ligation for copper-free click systems. In addition, we have identified several novel binding partners of benzimidazole probes: Isoform 2 of deleted in malignant brain tumors 1 protein (DMBT1) and three uncharacterized proteins.

Molecular BioSystems 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, Application In Synthesis of 359860-27-8.

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

Yang, Qingxi published the artcileThe dissipation of cyazofamid and its main metabolite CCIM during tomato growth and tomato paste making process, Product Details of C11H8ClN3, the publication is Food Additives & Contaminants, Part A (2019), 36(9), 1327-1336, database is CAplus and MEDLINE.

In several studies focused on the residues of cyazofamid and its main metabolite 4-chloro-5-p-tolylimidazole-2-carbonitrile (CCIM) on tomato where it is widely used, CCIM has been shown to have higher acute toxicity than cyazofamid, and this is crucial to evaluate the potential food risk of cyazofamid and CCIM. In this study, the dissipation of cyazofamid and CCIM during tomato growth and tomato paste making process were assessed. The targeted compounds cyazofamid and CCIM were determined by LC-MS/MS. The results indicated that the half-life of cyazofamid was 4.6 days after applying in the field, and the maximum value of CCIM was 0.08 mg/kg at 3 days after the last application of cyazofamid, then gradually decreased. In addition, the concentrations of cyazofamid and CCIM were affected by different processing steps including washing, peeling, homogenisation, simmering, and sterilisation. Results showed that the mean losses of cyazofamid and CCIM were 92.3% and 75.2% after washing and peeling. The Processing Factor (PF) values were all less than 1. Especially for peeling, the PFs of cyazofamid and CCIM were 0.12 and 0.04, resp.

Food Additives & Contaminants, Part A published new progress about 120118-14-1. 120118-14-1 belongs to imidazoles-derivatives, auxiliary class Imidazole,Chloride,Nitrile,Benzene, name is 4-Chloro-5-(p-tolyl)-1H-imidazole-2-carbonitrile, and the molecular formula is C11H9NO3, Product Details of C11H8ClN3.

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

Liu, Jianming published the artcileConstruction of the flavones and aurones through regioselective carbonylative annulation of 2-bromophenols and terminal alkynes, Synthetic Route of 4760-35-4, the publication is Tetrahedron Letters (2013), 54(14), 1802-1807, database is CAplus.

The easily available and efficient catalyst containing a benzimidazolium ligand and PdCl₂(PPh₃)₂ demonstrated excellent catalytic activity to construct the flavones and aurones, resp. This reaction can be operated under mild conditions, affording the desired products in moderate to good yields. This protocol was used to prepare the flavones and aurones by a slight modification of amines.

Tetrahedron Letters 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, Synthetic Route of 4760-35-4.

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