Month: December 2022

Hwang, Jimin published the artcileSynthesis and evaluation of RNase L-binding 2-aminothiophenes as anticancer agents, Application of 4-Hydroxy-3,5-dimethoxybenzaldehyde, the publication is Bioorganic & Medicinal Chemistry (2022), 116653, database is CAplus and MEDLINE.

Aminothiophene is a scaffold that is widely present in drugs and biol. active small mols. as chem. probes. In this study, 43 compounds sharing a 2-aminothiophenone-3-carboxylate (ATPC) scaffold, known to activate the RNase L (RNase L), were synthesized and selected ATPCs showed enhancement of thermal stability of RNase L upon binding. Screening of antiproliferation activities against human cancer cell lines revealed that ATPCs represented by compounds 4l and 50 showed potent single-digit micromolar antiproliferation activity against human cancer cell lines. Compounds 4l and 50 exhibited time- and dose-dependent proliferation inhibition, induced cellular apoptosis measured by cleaved PARP and via flow cytometry, inhibited cell migration, and inhibited cell colony formation. Combining the results reported in this work, ATPCs were evaluated as potential anticancer agents mediated by RNase L-binding and apoptosis induction. The work contributes to the study on the polypharmacol. properties of aminothiophene-containing small mols.

Bioorganic & Medicinal Chemistry published new progress about 134-96-3. 134-96-3 belongs to ethers-buliding-blocks, auxiliary class Immunology/Inflammation,COX,Natural product, name is 4-Hydroxy-3,5-dimethoxybenzaldehyde, and the molecular formula is C9H10O4, Application of 4-Hydroxy-3,5-dimethoxybenzaldehyde.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Yang, Yong published the artcileUltrasonic synthesis of poly[2-methoxy-5-(2′-ethylhexyloxy)-p-phenylenevinylene], HPLC of Formula: 146370-51-6, the publication is Gaofenzi Xuebao (2006), 892-896, database is CAplus.

Poly[2-methoxy-5-(2′-ethylhexyloxy)-p-phenylenevinylene] (MEH-PPV) is a typical example of solution processable conjugated polymers for polymeric light emitting diodes application, which shows good solubility in common organic solvents. However, gelation or micro-gelation always occurs during the polymerization process. Herein, we report the synthesis of fully soluble MEH-PPV by ultrasonic irradiation method. The raw material was 4-methoxyphenol, and ultrasonic irradiation method was used in the etherification, bromomethylation and polymerization The polymer is prepared from the bis-bromomethyl monomer through the Gilch route. Compared with the conventional mech. stirring, ultrasonic irradiation method has shown great advantages with respect to the shorter reaction time, lower reaction temperature, higher yields and higher mol. weight (M_n) of MEH-PPV. The optimized reaction conditions including reaction solvent, temperature, and time, were determined for the related etherification, bromomethylation and polymerization with ultrasonic method. Especially, using ultrasonic method, the gelation in the polymerization had been overcome. MEH-PPV obtained was fully soluble in THF and chloroform and no gel or micro-gel existed. The structures of the intermediate products and MEH-PPV were determined by IR and ¹H-NMR. It was found the MEH-PPV synthesized by ultrasonic irradiation processes had higher luminescence quantum efficiency than that by mech. stirring.

Gaofenzi Xuebao published new progress about 146370-51-6. 146370-51-6 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 1-((2-Ethylhexyl)oxy)-4-methoxybenzene, and the molecular formula is C10H6Br2, HPLC of Formula: 146370-51-6.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Liu, Luo-Yan published the artcilemeta C-H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity, Recommanded Product: 2-Isopropylanisole, the publication is Journal of the American Chemical Society (2019), 141(37), 14870-14877, database is CAplus and MEDLINE.

Controlling site selectivity of C-H activation without using a directing group remains a significant challenge. While Pd(II) catalysts modulated by a mutually repulsive pyridine-type ligand have been shown to favor the relatively electron-rich carbon centers of arenes, reversing the selectivity to favor palladation at the relatively electron-deficient positions has not been possible. Herein we report the first catalytic system that effectively performs meta C-H arylation of a variety of alkoxy aromatics including 2,3-dihydrobenzofuran and chroman with exclusive meta site selectivity, thus reversing the conventional site selectivity governed by native electronic effects. The identification of an effective ligand and modified norbornene (NBE-CO₂Me), as well as taking advantage of the statistics, are essential for achieving the exclusive meta selectivity.

Journal of the American Chemical Society published new progress about 2944-47-0. 2944-47-0 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 2-Isopropylanisole, and the molecular formula is C10H14O, Recommanded Product: 2-Isopropylanisole.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Upadhyaya, Punit published the artcileInhibition of Ras Signaling by Blocking Ras-Effector Interactions with Cyclic Peptides, Safety of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Angewandte Chemie, International Edition (2015), 54(26), 7602-7606, database is CAplus and MEDLINE.

Ras genes are frequently activated in human cancers, but the mutant Ras proteins remain largely “undruggable” through the conventional small-mol. approach owing to the absence of any obvious binding pockets on their surfaces. By screening a combinatorial peptide library, followed by structure-activity relationship (SAR) anal., we discovered a family of cyclic peptides possessing both Ras-binding and cell-penetrating properties. These cell-permeable cyclic peptides inhibit Ras signaling by binding to Ras-GTP and blocking its interaction with downstream proteins and they induce apoptosis of cancer cells. Our results demonstrate the feasibility of developing cyclic peptides for the inhibition of intracellular protein-protein interactions and of direct Ras inhibitors as a novel class of anticancer agents.

Angewandte Chemie, International Edition published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C9H17NO, Safety of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Kirchnerova, Jitka published the artcileThe mechanism of the electrochemical oxidation of thiourea, Related Products of ethers-buliding-blocks, the publication is Analytica Chimica Acta (1981), 83-95, database is CAplus.

Cyclic voltammetry and potentiostatic coulometry were used to study the electrochem. oxidation of thiourea [62-56-6] in aqueous solutions of HNO₃, HNO₃-NH₄NO₃, and NH₄NO₃-NH₄OH in MeCN. These studies were carried out at glassy C and/or Pt working electrodes. In MeCN, the cyclic voltammograms show 1 oxidation peak at ±0.6 V and a reduction peak at -0.1 V. In aqueous solutions up to about pH 6, there is a 2nd oxidation peak at 1.3 V which is irreversible and its height is sensitive to acidity. These experiments have confirmed that in acidic and neutral solutions, the oxidation of thiourea proceeds via a slow 1-electron transfer reaction producing a (NH₂)₂CS radical cation [61347-13-5]. Further direct oxidation of this radical takes place only at higher potentials (∼1.2 V) and involves hydration and proton-transfer equilibrium Otherwise, C,C‘-dithiodiformamidinium ion [64035-50-3] is formed by a fast dimerization reaction. Coulometric and chronopotentiometric measurements showed that in strong acid, the 2nd oxidation step involves 1 electron, while at lower acidities the further oxidation involving 3 (and possibly 5 electrons) proceeds in 2 (or 3) steps of very similar potential.

Analytica Chimica Acta published new progress about 14807-75-1. 14807-75-1 belongs to ethers-buliding-blocks, auxiliary class Salt,Thiourea,Amine,Aliphatic hydrocarbon chain, name is Formamidine disulfide dihydrochloride, and the molecular formula is C2H8Cl2N4S2, Related Products of ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Fu, Xiangkai published the artcilePerfluorooctanesulfonic acid catalyzed Friedel-Crafts alkylation with olefins in gas-liquid phase, Application In Synthesis of 2944-47-0, the publication is Chinese Chemical Letters (1993), 4(4), 307-10, database is CAplus.

Solid superacid perfluorooctanesulfonic acid (POSA) catalyzed Friedel-Crafts alkylation of aromatic hydrocarbons with olefins in gas-liquid phase. The alkylations gave good yields with simple operation and easy work up. The amount of the catalyst used in the reactions was small and could be reused. The optimum temperature of the reactions and the effect of the amount of the catalyst used in the reactions are also discussed.

Chinese Chemical Letters published new progress about 2944-47-0. 2944-47-0 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 2-Isopropylanisole, and the molecular formula is C10H14O, Application In Synthesis of 2944-47-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Rochon, Kristina published the artcilePreparation and Evaluation at the Delta Opioid Receptor of a Series of Linear Leu-Enkephalin Analogues Obtained by Systematic Replacement of the Amides, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is ACS Chemical Neuroscience (2013), 4(8), 1204-1216, database is CAplus and MEDLINE.

Leu-enkephalin analogs, in which the amide bonds were sequentially and systematically replaced either by ester or N-Me amide bonds, were prepared using classical organic chem. as well as solid-phase peptide synthesis (SPPS). The peptidomimetics were characterized using competition binding, ERK1/2 phosphorylation, receptor internalization, and contractility assays to evaluate their pharmacol. profile over the delta opioid receptor (DOPr). The lipophilicity (LogD_7.4) and plasma stability of the active analogs were also measured. The results here revealed that the last amide bond can be successfully replaced by either an ester or an N-Me amide bond without significantly decreasing the biol. activity of the corresponding analogs when compared to Leu-enkephalin. The peptidomimetics with an N-Me amide function between residues Phe and Leu were found to be more lipophilic and more stable than Leu-enkephalin. Findings from the present study further revealed that the hydrogen-bond donor properties of the fourth amide of Leu-enkephalin are not important for its biol. activity on DOPr. In addition, the results showed that the systematic replacement of amide bonds by isosteric functions represents an efficient way to design and synthesize novel peptide analogs with enhanced stability. In conclusion, the authors suggest that such a strategy can also be useful to study the biol. roles of amide bonds.

ACS Chemical Neuroscience published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Kumaresan, R. published the artcileSynthesis and evaluation of N,N-di-alkyl-2-methoxyacetamides for the separation of U(VI) and Pu(IV) from nitric acid medium, COA of Formula: C3H7NO2, the publication is Radiochimica Acta (2017), 105(9), 699-707, database is CAplus.

The homologs of N,N-di-alkyl-2-methoxyacetamides (DAMeOA) having three different alkyl chains varying from hexyl to decyl (C₆, C₈ and C₁₀) were synthesized and characterized by NMR and IR spectral analyses. Extraction behavior of U(VI) and Pu(IV) from nitric acid medium in a solution of 0.5 M of DAMeOA in n-dodecane (n-DD) was studied and the results were compared with those obtained using N,N-di-hexyloctanamide (DHOA) in n-dodecane. The effect of various parameters on the distribution ratio of U(VI) and Pu(IV) in DAMeOA was studied. The extraction of nitric acid increased with decrease in chain length of alkyl group attached to amidic nitrogen atom of DAMeOA and the conditional nitric acid extraction constant was determined The extraction of nitric acid in DAMeOA/n-DD resulted in the formation of third phase in organic phase and the third phase occurred early with DAMeOA having smaller alkyl chain length. In contrast to this, the distribution ratio (D) of U(VI) and Pu(IV) in DAMeOA/n-DD increased with increase in the concentration of nitric acid and with increase in the chain length of alkyl group attached to amidic nitrogen atom of DAMeOA. The stoichiometry of the metal – solvate was determined from the slope of extraction data. Quant. recovery of uranium and plutonium from the loaded organic phase was achieved using dilute nitric acid.

Radiochimica Acta published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, COA of Formula: C3H7NO2.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Manjunathan, Pandian published the artcileExploring tailor-made Bronsted acid sites in mesopores of tin oxide catalyst for β-alkoxy alcohol and amino alcohol syntheses, Recommanded Product: 2-Methoxypropan-1-ol, the publication is Scientific Reports (2021), 11(1), 15718, database is CAplus and MEDLINE.

The generation of Bronsted (Sn-OH) and Lewis (coordinatively unsaturated metal centers) acidic sites on the solid surface is a prime demand for catalytic applications. Mesoporous materials are widely employed as catalysts and supports owing to their different nature of acidic sites. Nevertheless, the procedure adopted to generate acid functionalities in these materials involves tedious steps. Herein, we report the tunable acidic sites containing Bronsted sites with relatively varied acid strength in tin oxide by employing soft template followed by simple thermal treatment at various temperatures The readily accessible active sites, specifically Bronsted acidic sites distributed throughout the tin oxide framework as well as mesoporosity endow them to perform with exceptionally high efficiency for epoxide ring opening reactions with excellent reusability. These features promoted them to surpass stannosilicate catalysts for the epoxide ring opening reactions with alc. as a nucleophile and the study was extended to aminolysis of epoxide with the amine. The existence of relatively greater acid strength and numbers in T-SnO₂-350 catalyst boosts to produce a high amount of desired products over other tin oxide catalysts. The active sites responsible in mesoporous tin oxide for epoxide alcoholysis were studied by poisoning the Bronsted acidic sites in the catalyst using 2,6-lutidine as a probe mol.

Scientific Reports published new progress about 1589-47-5. 1589-47-5 belongs to ethers-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ether, name is 2-Methoxypropan-1-ol, and the molecular formula is C4H10O2, Recommanded Product: 2-Methoxypropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Brown, Herbert C. published the artcileChiral synthesis via organoboranes. 9. Crystalline chelates from borinic and boronic esters. A simple procedure for upgrading borinates and boronates to materials approaching 100% optical purity, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane, the publication is Journal of Organic Chemistry (1986), 51(24), 4526-30, database is CAplus.

The synthesis of crystalline chelates from borinate and boronate esters was explored as a means of upgrading the optical purities of intermediates from asym. hydroboration. B-Methoxy-9-borabicyclo[3.3.1]nonane and Me dicyclohexyl- and diisopinocampheylborinate react with various amino alcs. to form the corresponding chelates. Crystallization of 2-pyrrolidinylmethyl isopinocampheyl exo-norbornylborinate of 83% enantiomeric excess (e.e.) gives a product approaching 100% e.e. Treating di-Me cyclopentyl-, exo-norbornyl- and siamylboronate with various amino diols gave the corresponding boronates. The formation of the B←N bond depends on both steric and electronic factors. The corresponding boronates (2:1 derivatives) derived from these typical di-Me boronates and tetrols were also prepared The chelate derived from di-Et 3-tetrahydropyranylboronate of 83% e.e. and (HOCH₂CH₂)₂NCH₂CH₂N(CH₂CH₂OH)₂ yields a product of optical purity ≤100% e.e. upon crystallization

Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem