Tag: M.W=150-200

Carvalho, Thiago O.; Carvalho, Pedro H. P. R.; Correa, Jose R.; Guido, Bruna C.; Medeiros, Gisele A.; Eberlin, Marcos N.; Coelho, Sara E.; Domingos, Josiel B.; Neto, Brenno A. D. published the artcile< Palladium Catalyst with Task-Specific Ionic Liquid Ligands: Intracellular Reactions and Mitochondrial Imaging with Benzothiadiazole Derivatives>, Recommanded Product: 1-carboxymethyl-3-methylimidazolium chloride, the main research area is palladium catalyst ionic liquid ligand mitochondria imaging benzothiadiazole.

A water-soluble and charge-tagged palladium complex (PdMAI) was found to function inside breast cancer live cells of the MCF-7 lineage as an efficient catalyst for cross-coupling reaction. PdMAI, bearing two ionophilic task-specific ionic liquids as ligands, efficiently catalyzed both in cellulo Suzuki and Buchwald-Hartwig amination reactions. For the first time, therefore, the Buchwald-Hartwig amination is described to occur inside the highly complex cellular environment. The 2,1,3-benzothiadiazole (BTD) core was used as the base for the syntheses, and two π-extended fluorescent derivatives (BTD-2APy) and (BTD-1AN), which were found to emit in the green and red channels, had impressive mitochondrial affinity. These chromophores allowed for selective mitochondrial imaging and tracking.

Journal of Organic Chemistry published new progress about Benzothiadiazoles Role: BUU (Biological Use, Unclassified), SPN (Synthetic Preparation), BIOL (Biological Study), USES (Uses), PREP (Preparation). 700370-07-6 belongs to class imidazoles-derivatives, and the molecular formula is C6H9ClN2O2, Recommanded Product: 1-carboxymethyl-3-methylimidazolium chloride.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Letavic, Michael A.; Ly, Kiev S. published the artcile< Microwave assisted, palladium catalyzed aminocarbonylations of heteroaromatic bromides using solid Mo(CO)6 as the carbon monoxide source>, Application of C4H5BrN2, the main research area is heteroaromatic amide preparation microwave irradiation; amine heteroaromatic bromide molybdenum carbonyl aminocarbonylation amidation palladium catalysis.

The direct conversion of a variety of heteroaromatic bromides into heteroaromatic amides is described. This reaction utilizes Mo(CO)6 as the carbon monoxide source and is performed using microwave heating allowing for very short reaction times. This convenient methodol. allows for the preparation of a variety of heteroaromatic amides, e.g. I, which are useful in medicinal chem. applications.

Tetrahedron Letters published new progress about Amidation. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Application of C4H5BrN2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Besseau, Francois; Graton, Jerome; Berthelot, Michel published the artcile< A theoretical evaluation of the pKHB and ΔH-HB hydrogen-bond scales of nitrogen bases>, COA of Formula: C4H5BrN2, the main research area is theory pK hydrogen bond basicity nitrogen base.

The exptl. pKHB hydrogen-bond (HB) basicity scale and the corresponding ΔH-hB enthalpic scale of nitrogen compounds are extended and analyzed in light of simple theor. descriptors using the B3LYP d. functional method and a medium-size basis set (6-31 + G(d,p)). The selected training set includes 59 monofunctional unhindered nitrogen bases for which homogeneous and accurate exptl. pKHB and ΔH-HB data have been determined by means of the association equilibrium of the bases with a reference hydrogen-bond acid, 4-fluorophenol, in CCl4. The three hybridization states encountered in the nitrogen atom, sp, sp2 and sp3, are equally represented in this data set. A proper estimation of their exptl. enthalpy (ΔH-HB) is directly attainable from the theor. enthalpy of the complexation reaction with hydrogen fluoride (ΔH-(HF)). However, a second parameter is required to calculate with good accuracy the exptl. free energy of association represented by pKHB. About 99% of the variance of the pKHB scale is described by a bilinear equation using the min. electrostatic potential (VS,min) of the monomer in addition to the interaction energy (D(HF)0). The equations are tested for an external set of 99 addnl. compounds including very different nitrogen bases such as ortho-substituted pyridines, polyazines and azoles. Theor. calculations give a reliable estimation of hydrogen-bond basicity provided that the populations of the different isomers of the bases are taken into account by using the Boltzmann law, and that a specific halogen-bond interaction with the solvent CCl4 is considered for polybasic mols. The pKHB scale can thus be extended to important classes of species exptl. inaccessible in CCl4, to polynitrogen compounds and to mols. of biol. significance.

Chemistry – A European Journal published new progress about Complexation enthalpy (Hydrogen bond). 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, COA of Formula: C4H5BrN2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Butler, Richard Noel published the artcile< Proton nuclear magnetic resonance spectra of aryl and mono- and disubstituted N-methylazoles>, Synthetic Route of 1003-21-0, the main research area is NMR methylazole; pyrazole tetrazole imidazole NMR.

Proton NMR spectra of substituted azoles, e.g., methylpyrrole, imidazoles, pyrazoles, etc., are compared. The influence of the azole ring on the chem. shifts of phenyl protons is discussed. A correlation between N-Me chem. shifts and the structural characteristics of the N-Me group in mono- and disubstituted azoles is noted.

Canadian Journal of Chemistry published new progress about Molecular structure-property relationship. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Synthetic Route of 1003-21-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Amaudrut, Jerome; Argiriadi, Maria A.; Barth, Martine; Breinlinger, Eric C.; Bressac, Didier; Broqua, Pierre; Calderwood, David J.; Chatar, Mohamed; Cusack, Kevin P.; Gauld, Stephen B.; Jacquet, Sebastien; Kamath, Rajesh V.; Kort, Michael E.; Lepais, Valerie; Luccarini, Jean-Michel; Masson, Philippe; Montalbetti, Christian; Mounier, Laurent; Potin, Dominique; Poupardin, Olivia; Rouaud, Sylvie; Spitzer, Luc; Wallace, Craig D. published the artcile< Discovery of novel quinoline sulphonamide derivatives as potent, selective and orally active RORγ inverse agonists>, Category: imidazoles-derivatives, the main research area is RORgamma agonist IL17 nuclear hormone receptor SAR; IL-17; Nuclear hormone receptor; RORγt inverse agonist; SAR; Th17 cells.

A high-throughput screen against Inventiva’s compound library using a Gal4/RORγ-LBD luciferase reporter gene assay led to the discovery of a new series of quinoline sulfonamides as RORγ inhibitors, eventually giving rise to a lead compound having an interesting in vivo profile after oral administration. This lead was evaluated in a target engagement model in mouse, where it reduced IL-17 cytokine production after immune challenge. It also proved to be active in a multiple sclerosis model (EAE) where it reduced the disease score. The synthesis, structure activity relationship (SAR) and biol. activity of these derivatives is described herein.

Bioorganic & Medicinal Chemistry Letters published new progress about Autoimmune disease. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Category: imidazoles-derivatives.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Linciano, Pasquale; Sorbi, Claudia; Comitato, Antonella; Lesniak, Anna; Bujalska-Zadrozny, Magdalena; Pawlowska, Agata; Bielenica, Anna; Orzelska-Gorka, Jolanta; Kedzierska, Ewa; Biala, Grazyna; Ronsisvalle, Simone; Limoncella, Silvia; Casarini, Livio; Cichero, Elena; Fossa, Paola; Satala, Grzegorz; Bojarski, Andrzej J.; Brasili, Livio; Bardoni, Rita; Franchini, Silvia published the artcile< Identification of a Potent and Selective 5-HT1A Receptor Agonist with In Vitro and In Vivo Antinociceptive Activity>, Safety of 5-Bromo-1-methyl-1H-imidazole, the main research area is pain 5HT1A receptor agonist preparation analgesic; 5-HT1AR agonists; Serotonin receptors; behavioral profiling; mice; pain.

Opioids are the gold standard drugs for the treatment of acute and chronic severe pain, although their serious side effects constitute a big limitation. In the search for new and safer drugs, 5-HT1AR agonists are emerging as potential candidates in pain relief therapy. In this work, we evaluated the affinity and activity of enantiomers of the two newly synthesized, potent 5-HT1AR agonists N-[(2,2-diphenyl-1,3-dioxolan-4-yl)methyl]-2-[2-(pyridin-4-yl)phenoxy]ethan-1-ammonium hydrogenoxalate (rac-1) and N-((2,2-diphenyl-1,3-dioxolan-4-yl)methyl)-2-(2-(1-methyl-1H-imidazol-5-yl)phenoxy)ethan-1-ammonium hydrogenoxalate (rac-2) in vitro and in vivo. The role of chirality in the interaction with 5-HT1AR was evaluated by mol. docking. The activity of the rac-1 was tested in mouse models of acute pain (hot plate) and severe tonic nociceptive stimulation (intraplantar formalin test). Rac-1 was active in the formalin test with a reduction in paw licking in both phases at 10 mg/kg, and its effect was abolished by the selective 5-HT1AR antagonist, WAY-100635. The eutomer (S)-1, but not the racemate, was active during the hot plate test at 10 and 20 mg/kg, and this effect was abolished by 30 min treatment with WAY-100635 at 30 min. Similarly to 8-OH-DPAT, (S)-1 evoked a slow outward current and depressed spontaneous glutamatergic transmission in superficial dorsal horn neurons, more effectively than rac-1. The eutomer (S)-1 showed promising developability properties, such as high selectivity over 5-HT subtypes, no interaction with the μ receptors, and low hepato- and cardiotoxicity. Therefore, (S)-1 may represent a potential candidate for the treatment of acute and chronic pain without having the adverse effects that are commonly associated with the classic opioid drugs.

ACS Chemical Neuroscience published new progress about 5-HT1A agonists. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Safety of 5-Bromo-1-methyl-1H-imidazole.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Inoue, Hiroo; Hayashi, Shigeki; Imoto, Eiji published the artcile< Electrical conductivity of heterocyclic compounds. Molecular complexes of phenazine>, Application In Synthesis of 1003-21-0, the main research area is .

The composition, color, and m.p. of mol. complexes of the salt type prepared from phenazine hydro-chloride (I) or methosulfate and pyrene (II) or p-hydroquinone (III) varied with drying conditions. Thus, the N content and resistivity increased and the Cl content and m.p. decreased with increased drying times over P2O5 at reduced pressure. The ultraviolet spectra of I-II in a KBr pellet showed an absorption band at ∼620 mμ. The electron spin resonance spectra showed an unpaired electron localized on the N atom of II. The salt-type mol. complexes had a lower resistivity than the non-salt type. Thus, the sp. resistivities of I-III and II-III were 3 × 1011 and 3 × 1015 ohm-cm., res.

Bulletin of the Chemical Society of Japan published new progress about Heterocyclic compounds. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Application In Synthesis of 1003-21-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Lin, Fang; Wang, Hao; Liu, Wei; Li, Jing published the artcile< Zero-dimensional ionic antimony halide inorganic-organic hybrid with strong greenish yellow emission>, Recommanded Product: 1-carboxymethyl-3-methylimidazolium chloride, the main research area is ionic antimony halide inorganic organic hybrid greenish yellow emission; crystallog ionic antimony halide inorganic organic hybrid.

Here, we reported a new zero-dimensional ionic antimony halide inorganic-organic hybrid structure, H3SbBr6(L)6 (L = 2-(3-methyl-1H-imidazol-3-ium-1-yl)acetate). The inorganic component is a mol. SbBr63- anion with an octaheral geometry for the metal. Each individual anion is surrounded by six organic ligands. The compound emits bright green-yellow light with high quantum efficiency (IQY = 55% at λex = 360 nm). Combined with its low toxicity and high stability, the title compound serves as a good example of lighting phosphors based on antimony halide hybrid materials.

Journal of Materials Chemistry C: Materials for Optical and Electronic Devices published new progress about Band structure. 700370-07-6 belongs to class imidazoles-derivatives, and the molecular formula is C6H9ClN2O2, Recommanded Product: 1-carboxymethyl-3-methylimidazolium chloride.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ohba, Masashi; Mukaihira, Takafumi; Fujii, Tozo published the artcile< Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines>, HPLC of Formula: 1003-21-0, the main research area is asym synthesis arylthiomethylhistidine; histidine arylthio asym synthesis; formal synthesis starfish alkaloid imbricatine; ovothiol A C formal synthesis.

Chiral syntheses of 3-methyl-5-(arylthio)-L-histidines I (R = Ph, 1-naphthyl), selected as models for the asteroid alkaloid imbricatine, have been accomplished through a 10-step route starting from 4(5)-bromoimidazole (II). The key steps involved were methylation of II, hydroxymethylation of 4-bromo-1-methyl-1H-imidazole, replacement of the 4-bromo group by an arylthio group, and introduction of a chiral α-amino acid moiety into the chlorides III by the bislactim ether method. The synthesis of 4-(4-methoxybenzyl)thio analog III (R = 4-MeOC6H4CH2), carried out in a similar manner, concluded formal syntheses of ovothiols A and C.

Chemical & Pharmaceutical Bulletin published new progress about Stereoselective synthesis. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, HPLC of Formula: 1003-21-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Hu, Miao; Lin, Zidong; Li, Jianxiao; Wu, Wanqing; Jiang, Huanfeng published the artcile< Palladium-catalyzed ionic liquid-accelerated oxidative annulation of acetylenic oximes with unactivated long-chain enols>, Formula: C6H9ClN2O2, the main research area is isoxazole regioselective green preparation; oxime acetylenic enol oxidative annulation alkylation tandem palladium catalyst; allyl alc oxime oxidative annulation allylation tandem palladium catalyst.

A method was developed for the synthesis of isoxazoles such as I [R1 = H, Me, 4-BrC6H4, etc.; R2 = Pr, cyclopentyl, 4-MeC6H4, etc.; R3 = H, Br, n-Pr, etc.; X = CH2, O; n = 1, 2, 3, 4, 5] via palladium-catalyzed ionic liquid-accelerated oxidative cascade annulation/functionalization of acetylenic oximes with unactivated long chain enols/allylic alcs. under aerobic conditions. This newly developed protocol provides the rapid and straightforward synthetic strategy for the assembly of structurally diverse isoxazole architectures under mild conditions with high atom- and step-economy and exceptional functional group tolerance. Notably, the ionic liquid acts as not only a solvent in the reaction but also provided the excess halide ions to eliminate hydrochloride from acetylenic oximes. Moreover, this catalytic system could be recycled up to eight times and reused without significant loss of the catalytic activity.

Green Chemistry published new progress about Alcohols, unsaturated Role: RCT (Reactant), RACT (Reactant or Reagent). 700370-07-6 belongs to class imidazoles-derivatives, and the molecular formula is C6H9ClN2O2, Formula: C6H9ClN2O2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem