Month: October 2022

Kollar, Levente; Gobec, Martina; Szilagyi, Bence; Proj, Matic; Knez, Damijan; Abranyi-Balogh, Peter; Petri, Laszlo; Imre, Timea; Bajusz, David; Ferenczy, Gyorgy G.; Gobec, Stanislav; Keseru, Gyorgy M.; Sosic, Izidor published an article in 2021. The article was titled 《Discovery of selective fragment-sized immunoproteasome inhibitors》, and you may find the article in European Journal of Medicinal Chemistry.Reference of 1H-Benzo[d]imidazol-2-amine The information in the text is summarized as follows:

Proteasomes contribute to maintaining protein homeostasis and their inhibition is beneficial in certain types of cancer and in autoimmune diseases. However, the inhibition of the proteasomes in healthy cells leads to unwanted side-effects and significant effort has been made to identify inhibitors specific for the immunoproteasome, especially to treat diseases which manifest increased levels and activity of this proteasome isoform. Here, we report our efforts to discover fragment-sized inhibitors of the human immunoproteasome. The screening of an inhouse library of structurally diverse fragments resulted in the identification of benzo[d]oxazole-2(3H)-thiones, benzo[d]thiazole-2(3H)-thiones, benzo[d]imidazole-2(3H)-thiones, and 1-methylbenzo[d]imidazole-2(3H)-thiones (with a general term benzoXazole-2(3H)-thiones) as inhibitors of the chymotrypsin-like (β5i) subunit of the immunoproteasome. A subsequent structure-activity relationship study provided us with an insight regarding growing vectors. Binding to the β5i subunit was shown and selectivity against the β5 subunit of the constitutive proteasome was determined Thorough characterization of these compounds suggested that they inhibit the immunoproteasome by forming a disulfide bond with the Cys48 available specifically in the β5i active site. To obtain fragments with biol. more tractable covalent interactions, we performed a warhead scan, which yielded benzoXazole-2-carbonitriles as promising starting points for the development of selective immunoproteasome inhibitors with non-peptidic scaffolds. The results came from multiple reactions, including the reaction of 1H-Benzo[d]imidazol-2-amine(cas: 934-32-7Reference of 1H-Benzo[d]imidazol-2-amine)

1H-Benzo[d]imidazol-2-amine(cas: 934-32-7) can be used in the hydrolysis of a choline carbonate. It was also used in the synthesis of imidazo[1,2-a]benzimidazoles.Reference of 1H-Benzo[d]imidazol-2-amine

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Kweon, Jeonguk; Chang, Sukbok published an article in 2021. The article was titled 《Highly robust iron catalyst system for intramolecular C(sp3)-H amidation leading to γ-lactams》, and you may find the article in Angewandte Chemie, International Edition.Name: Di(1H-imidazol-1-yl)methanone The information in the text is summarized as follows:

Disclosed here is the use of an iron catalyst system for an intramol. C-H amidation toward γ-lactam synthesis from dioxazolone precursors. (Phthalocyanine)FeIIICl was found to catalyze this cyclization with extremely high turnover numbers of up to 47 000 under mild and aerobic conditions. On the basis of exptl. and computational mechanistic studies, the reaction is suggested to proceed by a stepwise radical pathway involving fast hydrogen atom abstraction followed by radical rebound. A plausible origin for the high turnover numbers along with air-compatibility is also rationalized. In addition to this study using Di(1H-imidazol-1-yl)methanone, there are many other studies that have used Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Name: Di(1H-imidazol-1-yl)methanone) was used in this study.

Di(1H-imidazol-1-yl)methanone(cas: 530-62-1) is a peptide coupling reagent,it is used in the synthesis of peptides. Reacts readily with carboxylic acids to form acyl imidazoles; subsequent reaction with amines to form amides goes smoothly.Name: Di(1H-imidazol-1-yl)methanone

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Recommanded Product: 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborateIn 2021 ,《Interplay of Structure and Dynamics in Lithium/Ionic Liquid Electrolytes: Experiment and Molecular Simulation》 was published in Journal of Physical Chemistry B. The article was written by Judeinstein, Patrick; Zeghal, Mehdi; Constantin, Doru; Iojoiu, Cristina; Coasne, Benoit. The article contains the following contents:

Despite their promising use in electrochem. and electrokinetic devices, ionic-liquid-based electrolytes often exhibit complex behavior arising from a subtle interplay of their structure and dynamics. Here, the authors report a joint exptl. and mol. simulation study of such electrolytes obtained by mixing 1-Bu 3-methylimidazolium tetrafluoroborate with Li tetrafluoroborate. More in detail, experiments consisting of x-ray scattering, pulsed field gradient NMR, and complex impedance spectroscopy are analyzed in the light of mol. dynamics simulations to probe the structural, dynamical, and electrochem. properties of this ionic-liquid-based electrolyte. Li addition promotes the nanostructuration of the liquid as evidenced from the appearance of a scattering prepeak that becomes more pronounced. Microscopically, using the partial structure factors determined from mol. dynamics, this prepeak is shown to correspond to the formation of well-ordered pos./neg. charge series and also large aggregates (Lin(BF4)4-m)(4-m+n)-, which develop upon Li addition Such nanoscale ordering entails a drastic decrease in both the mol. mobility and ionic conductivity In particular, the marked association of Li+ cations with four BF4- anions and long ion pairing times, which are promoted upon Li addition, severely hinder the Li+ transport properties. In the experiment, the researchers used 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6Recommanded Product: 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate)

3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6) is a member of lonic liquids. Actually, lonic liquids as innovative fluids have received wide attention only during the past two decades. The number of SCI papers published on lonic liquids has exponentially increased from a few in 1996 to >5000 in 2016, exceeding the annual growth rates of other popular scientific areas. Recommanded Product: 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Biotin interference: evaluation of a new generation of electrochemiluminescent immunoassays for high-sensitive troponin T and thyroid-stimulating hormone testing》 was written by Mzougui, Samy; Favresse, Julien; Soleimani, Reza; Fillee, Catherine; Gruson, Damien. Related Products of 58-85-5This research focused ontroponinT TSH electrochemiluminescent immunoassay; biotin; immunoassays; interference; thyroid-stimulating hormone (TSH); troponin. The article conveys some information:

Biotin is currently a matter of concern for laboratories using biotin-streptavidin-based immunoassays. Biotin interferences have been reported for high-sensitive troponin T (hsTnT) and TSH (TSH) assays. We aimed to evaluate the new generation of hsTnT and TSH electrochemiluminescent immunoassays announced to be less sensitive to biotin. Firstly, we assessed the anal. performances of new generation assays (imprecision, bias, total error, limit of quantification) and compared previous and new generation assays in the absence of biotin. Secondly, we challenged both generations of assays with samples spiked with seven different biotin levels. The efficiency of new generation assays was also compared to the streptavidin beads treatment. New generation assays presented suitable anal. performances. Previous and new generations of hsTnT and TSH assays were commutable in the absence of biotin. In the presence of biotin, we confirmed that previous generation assays were affected by biotin concentration as low as 40.5 ng/mL and that new generation assays were not affected up to the announced tolerance threshold of 1200 ng/mL. After the streptavidin beads treatment, we observed a higher imprecision for both parameters and a constant 10% neg. bias for TSH compared to new generation assays. New generation of electrochemiluminescent immunoassays appears as a reliable systematic solution to prevent biotin interference for hsTnT and TSH testing.5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5Related Products of 58-85-5) was used in this study.

5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5) may be used to elute proteins from avidin/streptavidin resins. It has been used for culturing of oligodendrocytes.Related Products of 58-85-5 And it has been used as a vitamin supplement for the growth of Bacillus species.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Design, synthesis and nematicidal activitives of trifluorobutene amide derivatives against Meloidogyne incognita》 was written by Yang, Haiping; Zhang, Ruifeng; Li, Zhong; Maienfisch, Peter; Xu, Xiaoyong. SDS of cas: 7720-39-0This research focused ontrifluorobutene amide derivative synthesis treatment nematode nematicide; Amide; In vitro; In vivo; Nematicidal activity; Trifluorobutene. The article conveys some information:

Plant parasitic nematodes have always been a pressing problem in the field of plant protection. Well-established chem. nematicides, especially organophosphorus and carbamates are the most used products for nematode control worldwide. Due to long-term overuse, they have developed serious resistance and new innovative solutions are urgently required. In this study, thirty-one novel trifluorobutene amide derivatives were designed and synthesized, and their nematicidal activities were determined Three different synthetic methods have been developed for the final amidation reaction enabling the successfully syntheses of the target compounds independently from the nucleophilicities of the substrate amino group. Most target compounds showed good nematicidal activity in our in vitro test. Among all the compounds, compounds I and II exhibited excellent nematicidal activity against Meloidogyne incognita, their LC50 values are 2.02 mg L-1 and 0.76 mg L-1, resp. In particular, compound II has found to be almost as active as the com. nematicide fluensulfone. Furthermore, most compounds gave full control (100% inhibition) of M. incognita at 40 mg L-1 in the in vivo tests in sandy soil, the best compounds were further investigated for in vivo activity in matrix soil. Among the compound tested, compound I showed excellent in vivo nematicidal activity. At a concentration of 5 mg L-1 still 56% inhibition was observed The results of our study indicate that compound I possesses excellent in vitro and in vivo nematicidal activity, and can be considered as promising lead mol. for further modification. In the part of experimental materials, we found many familiar compounds, such as 1H-Imidazol-2-amine(cas: 7720-39-0SDS of cas: 7720-39-0)

1H-Imidazol-2-amine(cas: 7720-39-0) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.SDS of cas: 7720-39-0

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of C27H38AuClN2On September 20, 2021 ,《Continuous Flow Synthesis of [Au(NHC)(Aryl)] (NHC = N-Heterocyclic Carbene) Complexes》 was published in Chemistry – A European Journal. The article was written by Cauwenbergh, Thibault; Tzouras, Nikolaos V.; Scattolin, Thomas; Bhandary, Subhrajyoti; Simoens, Andreas; Van Hecke, Kristof; Stevens, Christian V.; Nolan, Steven P.. The article contains the following contents:

The use of weak and inexpensive bases has recently opened promising perspectives towards the simpler and more sustainable synthesis of Au(I)-aryl complexes with valuable applications in catalysis, medicinal chem., and materials science. In recent years, continuous manufacturing has shown to be a reliable partner in establishing sustainable and controlled process scalability. Herein, the first continuous flow synthesis of a range of Au(I)-aryl starting from widely available boronic acids and various [Au(NHC)Cl] (NHC = N-heterocyclic carbene) complexes in unprecedentedly short reaction times and high yields is reported. Successful synthesis of previously non- or poorly accessible complexes exposed fascinating reactivity patterns. Via a gram-scale synthesis, convenient process scalability of the developed protocol was showcased. The results came from multiple reactions, including the reaction of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2Synthetic Route of C27H38AuClN2)

Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies. Synthetic Route of C27H38AuClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Knez, Damijan; Coquelle, Nicolas; Pislar, Anja; Zakelj, Simon; Jukic, Marko; Sova, Matej; Mravljak, Janez; Nachon, Florian; Brazzolotto, Xavier; Kos, Janko; Colletier, Jacques-Philippe; Gobec, Stanislav published their research in European Journal of Medicinal Chemistry on August 5 ,2018. The article was titled 《Multi-target-directed ligands for treating Alzheimer’s disease: Butyrylcholinesterase inhibitors displaying antioxidant and neuroprotective activities》.Computed Properties of C8H8N2O The article contains the following contents:

The limited clin. efficacy of current symptomatic treatment and minute effect on progression of Alzheimer’s disease has shifted the research focus from single targets towards multi-target-directed ligands. Here, a potent selective inhibitor of human butyrylcholinesterase was used as the starting point to develop a new series of multifunctional ligands. A focused library of derivatives was designed and synthesized that showed both butyrylcholinesterase inhibition and good antioxidant activity as determined by the DPPH assay. The crystal structure of compound 11 in complex with butyrylcholinesterase revealed the mol. basis for its low nanomolar inhibition of butyrylcholinesterase (Ki = 1.09±0.12 nM). In addition, compounds 8 and 11 show metal-chelating properties, and reduce the redox activity of chelated Cu2+ ions in a Cu-ascorbate redox system. Compounds 8 and 11 decrease intracellular levels of reactive oxygen species, and are not substrates of the active efflux transport system, as determined in Caco2 cells. Compound 11 also protects neuroblastoma SH-SY5Y cells from toxic Aβ1-42 species. These data indicate that compounds 8 and 11 are promising multifunctional lead ligands for treatment of Alzheimer’s disease. In the experiment, the researchers used 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Computed Properties of C8H8N2O)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
However, the application of imidazoles is not limited to the field of peptides and peptidomimetics. Computed Properties of C8H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2017,D’Attoma, Joseph; Camara, Titi; Brun, Pierre Louis; Robin, Yves; Bostyn, Stephane; Buron, Frederic; Routier, Sylvain published 《Efficient Transposition of the Sandmeyer Reaction from Batch to Continuous Process》.Organic Process Research & Development published the findings.Application In Synthesis of 2-Chloro-1H-benzo[d]imidazole The information in the text is summarized as follows:

The transposition of Sandmeyer chlorination from a batch to a safe continuous flow process was investigated. Our initial approach was to develop a cascade method using flow chem. which involved the generation of diazonium salt and its quenching with copper chloride. To achieve this safe diazotation continuous process, a chemometric approach (Simplex method) was used and extrapolated to establish a fully continuous flow method. The reaction scope was also examined via the synthesis of several (het)aryl chlorines. Validation and scale-up of the process were also performed. A higher productivity was obtained under increasingly tight security. The results came from multiple reactions, including the reaction of 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Application In Synthesis of 2-Chloro-1H-benzo[d]imidazole)

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) is an analog of benzimidazole that has been synthesized by Langmuir adsorption isotherm. It is a white crystalline solid that can be dissolved in water and hydrochloric acid. 2-Chloro-1H-benzo[d]imidazole inhibits the growth of herpes simplex virus by acting as a competitive inhibitor for the viral enzyme thymidine kinase, which catalyzes the conversion of thymine to thymidine.Application In Synthesis of 2-Chloro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2018,Archiv der Pharmazie (Weinheim, Germany) included an article by Keeley, Aaron; Abranyi-Balogh, Peter; Hrast, Martina; Imre, Timea; Ilas, Janez; Gobec, Stanislav; Keseru, Gyoergy M.. Electric Literature of C3H3BrN2. The article was titled 《Heterocyclic electrophiles as new MurA inhibitors》. The information in the text is summarized as follows:

An electrophilic fragment library of small heterocycles was developed and characterized in the surrogate GSH-reactivity assay and aqueous stability test that revealed their potential as covalent warheads. Screening the library against MurA from Staphylococcus aureus (MurASA) and Escherichia coli (MurAEC) identified heterocyclic fragments with significant inhibitory potency. The validated heterocyclic warhead library might be useful for developing targeted covalent inhibitors for other targets of interest with a new design strategy incorporating heterocyclic electrophiles as warheads. In addition to this study using 2-Bromo-1H-imidazole, there are many other studies that have used 2-Bromo-1H-imidazole(cas: 16681-56-4Electric Literature of C3H3BrN2) was used in this study.

2-Bromo-1H-imidazole(cas: 16681-56-4) is a member of imidazole. Its exclusive structural characteristics with enviable electron-rich features are favorable for imidazole-based fused heterocycles to bind efficiently with an array of enzymes and receptors in biological systems through various weak interactions like hydrogen bonds, ion-dipole, cation-π, π-π stacking, coordination, Van der Waals forces, hydrophobic effects, etc., and therefore they demonstrate widespread bioactivities. Electric Literature of C3H3BrN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Distance Angle Descriptors of the Interionic and Ion-Solvent Interactions in Imidazolium-Based Ionic Liquid Mixtures with Aprotic Solvents: A Molecular Dynamics Simulation Study》 were Koverga, Volodymyr A.; Smortsova, Yevheniia; Miannay, Francois Alexandre; Kalugin, Oleg N.; Takamuku, Toshiyuki; Jedlovszky, Pal; Marekha, Bogdan; Cordeiro, M. Natalia D. S.; Idrissi, Abdenacer. And the article was published in Journal of Physical Chemistry B in 2019. HPLC of Formula: 174501-65-6 The author mentioned the following in the article:

The aim of this paper is to quantify the changes of the interionic and ion-solvent interactions in mixtures of imidazolium-based ionic liquids, consisting tetrafluoroborat, hexafluorophosphate, trifluoromethylsulfonate, or bis(trifluoromethanesulfonyl)imide anions, and polar aprotic mol. solvents, such as acetonitrile (AN), γ-butyrolactone, and propylene carbonate. For this purpose, we calculate, using the nearest neighbor approach, the average distance between the imidazolium ring H atom in positions 2, 4 and 5 (H2,4,5) and the nearest high electronegativity atom of the solvent or anion (X) as distance descriptors, and the mean angle formed by the C2,4,5 H2,4,5 bond ant the H2,4,5… X axis around the H2,4,5 atom as angular descriptors of the cation-anion and cation-solvent interactions around the ring C H groups. The behavior of these descriptors as a function of the ionic liquid mole fraction is analyzed in detail. The obtained results show that the extent of the change of these descriptors with respect to their values in the neat ionic liquid depends both on the nature of the anion and on the mixture composition Thus, in the case of the mixtures of the mol. solvents with BmimBF4 and BmimTFO, a small change of the distance and a drastic increase of the angular descriptor corresponding to the cation-anion interactions is observed with decreasing mole fraction of the ionic liquid, indicating that the anion moves from the above/below position (with respect to the imidazolium ring plane) to a position that is nearly linearly aligned with the C2-H2 bond, and hinders the possible interaction between the C2-H2 group and the solvent mols. On the other hand, in the case of mixtures of BmimTFSI and BmimPF6 with the mol. solvents, both the observed increase of the distance descriptor and the slight change of the angular descriptor with decreasing ionic liquid mole fraction are compatible with the direct interactions of the solvent with the C2-H2 group. The behavior of these descriptors is correlated with the exptl. observed 1H chem. shift of the C2-H2 group and red shift of the C2 H2 vibrational mode, particularly at low ionic liquid mole fractions. The present results are thus of great help in interpreting these exptl. observations. In the part of experimental materials, we found many familiar compounds, such as 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6HPLC of Formula: 174501-65-6)

3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6) is a member of lonic liquids. Actually, lonic liquids as innovative fluids have received wide attention only during the past two decades. The number of SCI papers published on lonic liquids has exponentially increased from a few in 1996 to >5000 in 2016, exceeding the annual growth rates of other popular scientific areas. HPLC of Formula: 174501-65-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem