Month: December 2022

Vineberg, Jacob G. published the artcileDesign, Synthesis, and Biological Evaluations of Tumor-Targeting Dual-Warhead Conjugates for a Taxoid-Camptothecin Combination Chemotherapy, Quality Control of 359860-27-8, the publication is Journal of Medicinal Chemistry (2014), 57(13), 5777-5791, database is CAplus and MEDLINE.

Novel tumor-targeting dual-warhead camptothecin conjugates with SB-T-1214, (two warheads), self-immolative disulfide linkers for drug release, biotin as the tumor-targeting moiety, and 1,3,5-triazine as the tripod splitter module, were designed and synthesized. The potency of these conjugates were evaluated against MX-1, MCF-7, ID8, L1210FR (BR+, biotin receptor overexpressed) and WI38 (BR-, normal) cell lines in the absence and presence of glutathione (GSH), which is an endogenous thiol that triggers drug release inside the cancer cells. With the GSH and resuspension protocol, one of them exhibited IC₅₀ values of 3.22-9.80 nM against all BR+ cancer cell lines, and 705 nM against WI38. Thus, there was a two orders of magnitude higher selectivity to cancer cells. Also, a clear cooperative effect was observed for the taxoid-camptothecin combination when two drugs were delivered to the cancer cells specifically in the form of a dual-warhead conjugate.

Journal of 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 C8H8O2, Quality Control of 359860-27-8.

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

Mutti, Francesco G. published the artcileBiomimetic modelling of copper enzymes: synthesis, characterization, EPR analysis and enantioselective catalytic oxidations by a new chiral trinuclear copper(II) complex, Category: imidazoles-derivatives, the publication is European Journal of Inorganic Chemistry (2009), 554-566, database is CAplus.

The new octadentate ligand (R)-(+)-N,N’-dimethyl-N,N’-bis{-2-[bis(1-methyl-2-benzimidazolylmethyl)]-2-methyl-aminoethyl}-1,1′-binaphthyl-2,2′-diamine [(R)-(+)-DABN-L-Ala-Bz₄; L] was employed for the synthesis of dinuclear and trinuclear copper(II) complexes. The ligand design is based on the insertion of chiral residues derived from L-alanine between the diaminobinaphthyl (R)-(+)-DABN spacer and the aminobis(benzimidazole) metal binding units. The chiroptical properties of the ligand and the complexes are described. EPR experiments were performed on [Cu₂L]⁴⁺ and [Cu₃L]⁶⁺ at low temperatures In the case of [Cu₂L]⁴⁺, a weak dipolar interaction between the two spin centers was found. A similar weak spin interaction occurred in the trinuclear copper cluster, which could be treated likewise as a weakly coupled three-spin system. The anal. was substantiated by studying the complex EPR temperature behavior, where population of the quartet state occurred only at high temperature (77 K), whereas at cryogenic temperatures (4 K) the system adopted a doublet state as a ground-state spin configuration. Titration with sodium azide of [Cu₂L]⁴⁺ was consistent with terminal binding of one N₃^– mol. to each copper ion. Furthermore, dipolar interactions between spin centers were strongly suppressed in this case. For [Cu₃L]⁶⁺, the adduct formed by the interaction with two azido mols. induced formation of a μ-azido bridges among the three Cu²⁺ ions and led to population of the quartet state even at cryogenic temperatures This bridged configuration was, however, lost upon further addition of azido mols. The copper(II) complexes were tested as catalysts in the oxidation of biogenic catechols and flavonoids by dioxygen to give the corresponding quinones, which were trapped as adducts with MBTH. The dinuclear complex [Cu₂L]⁴⁺ displays poor substrate enantiodifferentiating ability, even though it exhibits catalytic activity comparable to that of [Cu₃L]⁶⁺. The trinuclear complex [Cu₃L]⁶⁺ exhibits significant enantioselectivity in the oxidations of the catecholamines L-/D-DOPA Me ester and L-/D-norepinephrine. The origin of this enantioselectivity must be associated with the mode of substrate binding, as it depends almost entirely on K_m.

European Journal of Inorganic 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

Pampalakis, G. published the artcile“Activography”: a novel, versatile and easily adaptable method for monitoring enzymatic activities in situ, Product Details of C18H34N4O5S, the publication is Chemical Communications (Cambridge, United Kingdom) (2017), 53(22), 3246-3248, database is CAplus and MEDLINE.

We developed “activog.” to map enzymic activities on tissue sections using activity-based probes. The assay was validated using a new protease-activity probe on skin biopsies to provide proof-of-concept. Activog. is more selective and tech. easier than the established in situ zymog., thus, adaptable in routine running clinico-chem. laboratories

Chemical Communications (Cambridge, United Kingdom) 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, Product Details of C18H34N4O5S.

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

Hyun, Jinho published the artcileMicrostamping on an activated polymer surfaces: Patterning biotin and streptavidin onto common polymeric biomaterials, Synthetic Route of 359860-27-8, the publication is Langmuir (2001), 17(20), 6358-6367, database is CAplus.

Microstamping on an activated polymer surface (MAPS) is a methodol. that enables biomols. to be patterned on polymers with micrometer spatial resolution MAPS combines homogeneous surface derivatization of a polymer to introduce a reactive functional group followed by reactive microcontact printing (μCP) of a biol. ligand of interest, linked to an appropriate reactive group. We demonstrate here that polyethylene, polystyrene, poly(Me methacrylate), and poly(ethylene terephthalate) films can be successfully modified to introduce COOH groups on their surfaces, which can be subsequently patterned by reactive μCP of amine-terminated biotin after derivatization of the COOH groups with pentafluorophenol. XPS and time-of-flight secondary ion mass spectrometry (TOF-SIMS) confirmed the chem. of MAPS at each stage of the derivatization of the polymer surfaces and reactive μCP of biotin. Micropatterned biotin surfaces fabricated by MAPS were patterned with streptavidin by exploiting mol. recognition between biotin and streptavidin. The formation of streptavidin patterns was examined by fluorescence microscopy of Alexa488-labeled streptavidin and by TOF-SIMS imaging of ¹⁵N-labeled recombinant streptavidin, bound to biotin patterns. The contrast in the streptavidin micropatterns was optimized by examining the effect of blocking agents and streptavidin incubation time. Maximum contrast was obtained for binding of 0.1 μM streptavidin from a buffer containing 0.02% (volume/volume) Tween 20 detergent for an incubation time of 1 min.

Langmuir 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, Synthetic Route of 359860-27-8.

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

Liu, Wen-Wen published the artcileFemtomole-Scale High-Throughput Screening of Protein Ligands with Droplet-Based Thermal Shift Assay, Recommanded Product: Sodium (S)-6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide, the publication is Analytical Chemistry (Washington, DC, United States) (2017), 89(12), 6678-6685, database is CAplus and MEDLINE.

There is a great demand to measure protein-ligand interactions in rapid and low cost way. Here the authors developed a microfluidic droplet-based thermal shift assay (dTSA) system for high throughput screening of small-mol. protein ligands. The system is composed of a nanoliter droplet array chip, a microfluidic droplet robot, and a real-time fluorescence detection system. Total 324 assays could be performed in parallel in a single chip with an 18 × 18 droplet array. The consumption of dTSA for each protein or ligand sample was only 5 nL (femtomole scale), which is significantly reduced by over 3 orders of magnitude compared with those in 96 or 384-well plate-based systems. The authors also observed the implementation of TSA in nanoliter droplet format could substantially improve assay precision with relative standard deviation (RSD) of 0.2% (n = 50), which can be ascribed to the enhanced thermal conduction in small volume reactors. The dTSA system was optimized by studying the effect of droplet volumes, as well as protein and fluorescent dye (SYPRO Orange) concentrations To demonstrate its potential in drug discovery, the authors applied the dTSA system in screening inhibitors of human thrombin with a com. library containing 100 different small mol. compounds, and two inhibitors were successfully identified and confirmed.

Analytical Chemistry (Washington, DC, United States) 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

Lu, Bing published the artcileIron-catalyzed esterification of allylic sp³ C-H bonds with carboxylic acids: Facile access to allylic esters, HPLC of Formula: 258278-25-0, the publication is Tetrahedron Letters (2017), 58(25), 2490-2494, database is CAplus.

The first general and efficient iron-catalyzed esterification of allylic sp³ C-H bonds with carboxylic acids using ionic iron(III) complexes as a catalyst and DTBP (DTBP = di-tert-Bu peroxide) as an oxidant is achieved. A variety of allylic esters were synthesized in good to excellent yields using an ionic iron(III) complex as catalyst in a 5 mol% loading. This reaction is characterized by its high efficiency, broad substrate scope with excellent steric hindrance tolerance and good functional group compatibility.

Tetrahedron Letters 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, HPLC of Formula: 258278-25-0.

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

Zhang, Xiao-qian published the artcileCationic polymerization of p-methylstyrene in ionic liquids media, Related Products of imidazoles-derivatives, the publication is Gaofenzi Xuebao (2019), 50(4), 375-383, database is CAplus.

In this study, cationic polymerization of p-methylstyrene (p-MeSt) was studied in ionic liquid (IL) reaction media. The effects of ILs on p-MeSt cationic polymerization were analyzed through d. functional theory (DFT) and exptl. method. The influences of various initiating systems on p-MeSt cationic polymerization were investigated, and the efficiencies of various ILs as reaction solvents were discussed. The structure of the polymerization product was characterized through ¹H-NMR and FTIR characterization analyses; number-average mol. weight (M_n) and mol. weight distribution were measured through gel permeation chromatog. (GPC); a temperature recorder tracked the relationship between polymerization system temperature variation and reaction time. The results showed that a CumOH (2-phenyl-2-propanol)/BF₃·OEt₂ initiating system is relatively effective in IL media over those frequently used in cationic polymerization reactions. The products polymerized in 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl) imide ([Bmim][NTf₂]) IL media have higher mol. weight and yield (up to 99%) and narrower mol. weight distribution (M_w/M_n is ∼ 2.0) than those in traditional mol. solvents (such as CH₂Cl₂). An anal. of the effects of ILs on polymerization indicated that ILs act as inert solvents in p-MeSt cationic polymerization and do not directly participate in the polymerization reaction. The ionic environment of IL cannot inhibit a chain transfer reaction completely, but can stabilize active species and disperse pos. charges. Thus, the polymerization reaction is milder in IL media than that in traditional mol. solvents. The results of IL recovery and reuse showed that these solvents can be used as reaction medium over a number of cycles without remarkable influence on the products. Finally, the corresponding elementary reaction mechanism of the cationic polymerization of p-MeSt initiated by the CumOH/BF₃·OEt₂ system in [Bmim][NTf₂] IL media was proposed in this study. As is known, ILs are recyclable and environmentally friendly green solvents. This study expands the reaction solvent of cationic polymerization and promotes the development of green chem.

Gaofenzi Xuebao published new progress about 862731-66-6. 862731-66-6 belongs to imidazoles-derivatives, auxiliary class Ionic Liquid, name is 1-octyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide, and the molecular formula is C18H28B2O4, Related Products of imidazoles-derivatives.

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

Qiu, Yingheng published the artcileDetermination of antazoline hydrochloride tablets by HPLC, Category: imidazoles-derivatives, the publication is Zhongguo Yaoye (2009), 18(1), 26-27, database is CAplus.

To establish an HPLC method for the determination of antazoline hydrochloride tablets. NUCLEODUR C₁₈ column was used, the mobile phase was 5 mmol/L sodium acetate (adjusted to pH 3.4 with glacial acetic acid)-triethylamine (100:0.2)-methanol (50:50), the flow rate was 1.0 mL/min, the wavelength of detection was 241 nm, and the column temperature was 35°. The good linearity was obtained over the range of 20.22-202.2 μg/mL. The average recovery rate was 99.83% (RSD = 0.53%; n = 6). The method is accurate and sensitive with better reproducibility. It can be suitable for controlling the quality of antazoline hydrochloride tablets.

Zhongguo Yaoye 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, Category: imidazoles-derivatives.

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

Li, Yan-Qing published the artcileQuinolinyl Imidazolidin-2-imine Nickel Catalyzed Efficient Copolymerization of Norbornene with para-Chlorostyrene, Category: imidazoles-derivatives, the publication is Chinese Journal of Polymer Science (2020), 38(9), 941-949, database is CAplus.

A series of novel quinolinyl imidazolidin-2-imine nickel complexes with different substituents on the imidazolidin-2-imine ligand were synthesized and characterized. The complexes in the presence of methylaluminoxane (MAO) as a cocatalyst catalyzed the copolymerization of norbornene (N) and styrene (S) or para-chlorostyrene (CS) with high activity (up to 1070 kg·mol^-1·h^-1). The installation of sterically bulky substituents on the imidazolidine-2-imine ligand was effective for the increase of the mol. weight and the comonomer content, affording high mol. weight copolymers with tunable CS content (0.57 mol%-11.7 mol%), in which the existence of Cl group can provide reaction site for the further functionalization of copolymers as well as the synthesis of graft or crosslinked polymers. The linear relationship between the comonomer content and the glass transition temperature of the copolymers and the monomer reactivity ratios in the copolymerization indicated the formation of the expected functionalized cyclic olefin copolymers (COC).

Chinese Journal of Polymer Science 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, Category: imidazoles-derivatives.

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

Yang, Hongbo published the artcileCharacterization of 8-Deuterium Substituted Proton Pump Inhibitors by Nuclear Magnetic Resonance and Electrospray Ionization Mass Spectrometry, Name: Sodium (S)-6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide, the publication is Analytical Letters (2015), 48(16), 2650-2660, database is CAplus.

NMR was employed to characterize the hydrogen-deuterium exchange for the proton pump inhibitors pantoprazole sodium, esomeprazole sodium, rabeprazole sodium, lansoprazole, and ilaprazole in methanol-d₄. The results showed that the ¹H and ¹³C signals of 8-CH₂ (labeled as H_8a, H_8b, and C₈) next to the sulfinyl (S⁼O) group of the proton pump inhibitors decreased significantly. Electrospray ionization mass spectrometry showed the presence of deuterated products. Basing on the NMR data, H_8a and H_8b of proton pump inhibitors were more active for the hydrogen-deuterium exchange. The most significant parameter governing the exchange was the salt-formation of the benzimidazole group. Therefore, the influence of salt-formation on hydrogen-deuterium exchange was characterized for ilaprazole; replacement of NH by N-Na on the benzimidazole group accelerated the exchange process. Tandem mass spectrometry showed that CH⁼S-OH was formed by tautomerism involving sulfinyl and CH₂ groups in methanol-d_4.

Analytical Letters 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 C9H6N2O4, Name: 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