Category: 104-01-8

Trillo, Paz published the artcileDirect Catalytic Reductive N-Alkylation of Amines with Carboxylic Acids: Chemoselective Enamine Formation and further Functionalizations, Quality Control of 104-01-8, the main research area is catalytic reductive alkylation amine carboxylic acid chemoselective enamine formation.

Direct reductive N-alkylation of secondary amines with carboxylic acids using molybdenum hexacarbonyl (5 mol %) as catalyst and diethoxymethylsilane as reducing agent generate enamines in a straightforward fashion in high yields. The formed enamines are without the need for isolation or purification further reacted with trimethylsilyl cyanide in the same reaction flask to yield α-amino nitriles in good yields. In the optimized reaction conditions equimolar amounts of carboxylic acid and amine are reacted under neat conditions, and a catalytic amount of trifluoroethanol (0.1 mol %) is added along with TMSCN for the cyanation step. The reductive N-alkylation reaction is demonstrated to be highly chemoselective, tolerating a multitude of different functional groups present in the starting carboxylic acids and amines. The reaction is scalable and the generated α-amino nitriles are converted to other useful compounds, e.g., α-amino acids or amino-tetrazoles. In addition, the intermediate enamines are further transformed into triazolines, sulfonylformamidines, pyrimidinediones, and TMS-propargylamines, resp., in high yields under mild reaction conditions. Benzoic acids react with secondary amines under similar conditions to give tertiary amines in high yields, and using this methodol., the biol. active compound Piribedil was isolated in 80% yield in a direct one-pot reaction setup.

ACS Catalysis published new progress about Amidines Role: SPN (Synthetic Preparation), PREP (Preparation) (sulfonylformamidines). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Quality Control of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Xia, Yujia published the artcileNH4I-promoted oxidative formation of benzothiazoles and thiazoles from arylacetic acids and phenylalanines with elemental sulfur, Name: 4-Methoxyphenylacetic acid, the main research area is arylbenzothiazole preparation; arylacetic acid amine sulfur oxidative cyclization catalyst ammonium iodide; benzyl arylthiazole preparation; aryl alanine sulfur oxidative cyclization catalyst ammonium iodide.

A NH4I/K3PO4-based catalytic system had been established to enable oxidative formation of thiazole compounds I [R1 = H, MeO; R2 = H, MeO, t-Bu; R3 = H, MeO; R1R2 = HC=CHCH=CH, HC=CHCH=N, HC=CHC(Br)=CH, HC=CHC(4-methoxyphenyl)=CH; R2R3 = OCH2O; Ar = Ph, 3-pyridyl, 2-naphthyl, etc.], II [Ar = Ph, 4-MeC6H4, 2,4-di-ClC6H3, etc.] from arylacetic acids and phenylalanines with elemental sulfur. While the three-component reaction of anilines or β-naphthylamines with arylacetic acids and elemental sulfur afforded benzo[2,1-d]thiazoles I [R1 = H, MeO; R2 = H, MeO, t-Bu; R3 = H, MeO; R2R3 = OCH2O; Ar = Ph] and naphtho[2,1-d]thiazoles, I [R1R2 = HC=CHCH=CH, HC=CHCH=N, HC=CHC(Br)=CH, HC=CHC(4-methoxyphenyl)=CH; Ar = Ph, 3-pyridyl, 2-naphthyl, etc.] the annulation of phenylalanines with elemental sulfur produces 2-benzyl II [Ar = Ph] and 2-benzoylthiazoles. This work well complements previous three-component annulations of benzothiazoles from other coupling partners.

Organic & Biomolecular Chemistry published new progress about Amino acids, analogs Role: RCT (Reactant), RACT (Reactant or Reagent) (phenylalanine). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Name: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Matos, Maria Joao published the artcileStructure-Based Optimization of Coumarin hA3 Adenosine Receptor Antagonists, Name: 4-Methoxyphenylacetic acid, the main research area is structure coumarin hA3 adenosine receptor antagonist; crystal structure.

Adenosine receptors are involved in several physiol. processes. Mols. able to selectively modulate one of these receptors represent promising multifunctional agents to treat or slow down the progression of different diseases. 3-Arylcoumarins have already been studied as neuroprotective agents by the group. Here, differently 8-substituted 3-arylcoumarins are complementarily studied as ligands of adenosine receptors, performing radioligand binding assays. Among the synthesized compounds, selective A3 receptor antagonists have been identified. 3-(4-Bromophenyl)-8-hydroxycoumarin (I) proved to be the most potent and selective A3 receptor antagonist (Ki = 258 nM). An anal. of its x-ray diffraction provided detailed information on its structure. Further evaluation of a selected series of compounds indicated that it is the nature and position of the substituents that determine their activity and selectivity. Theor. modeling calculations corroborate and explain the exptl. data, suggesting this novel scaffold has desirable properties for the development of potential multitarget drug candidates.

Journal of Medicinal Chemistry published new progress about Adenosine A3 receptor antagonists. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Name: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Estrada, Carl D. published the artcileEnantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is diol benzyl halide boron acid catalyst enantioselective alkylation desymmetrization; alc preparation.

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chair-like six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed “”methyl blocker”” on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodol. affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Journal of the American Chemical Society published new progress about Alkylation catalysts, stereoselective. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Recommanded Product: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Xu, Ruting published the artcileA rapid access to aliphatic sulfonyl fluorides, Formula: C9H10O3, the main research area is vinylsulfonyl fluoride tertiary carboxylic acid Eosin photochem decarboxylative fluorosulfonylethylation; alkyl sulfonyl fluoride preparation.

A facile and general approach for the synthesis of aliphatic sulfonyl fluorides via visible-light-mediated decarboxylative fluorosulfonylethylation was presented. The method is based on abundant carboxylic acid feed stock, applicable to various alkyl carboxylic acids including primary, secondary and tertiary acids and is also suitable for the modification of natural products like amino acids, peptides, as well as drugs, forging a rapid, metal-free approach to build sulfonyl fluoride compound libraries of considerable structural diversity. Further diversification of the SO2F-containing products was also demonstrated, which allows for access to a range of pharmaceutically important motifs such as sultam, sulfonate and sulfonamide.

Nature Communications published new progress about Carboxylic esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Formula: C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Scoville, David K. published the artcilePolybrominated Diphenyl Ethers and Gut Microbiome Modulate Metabolic Syndrome-Related Aqueous Metabolites in Mice, Application In Synthesis of 104-01-8, the main research area is gut microbiome polybrominated diphenyl ether metabolic syndrome aqueous metabolite.

Polybrominated di-Ph ethers (PBDEs) are persistent environmental toxicants associated with increased risk for metabolic syndrome. Intermediary metabolism is influenced by the intestinal microbiome. To test the hypothesis that PBDEs reduce host-beneficial intermediary metabolites in an intestinal microbiome-dependent manner, nine-week old male conventional (CV) and germ-free (GF) C57BL/6 mice orally gavaged once daily with vehicle, BDE-47, or BDE-99 (100μmol/kg) for four-days. Intestinal microbiome (16S rDNA sequencing), liver transcriptome (RNA-Seq), and intermediary metabolites in serum, liver, as well as small and large intestinal contents (SIC and LIC; LC-MS) were examined Changes in intermediary metabolite abundances in serum, liver, and SIC, were observed under basal conditions (CV vs. GF mice) and by PBDE exposure. PBDEs altered the largest number of metabolites in the LIC; most were regulated by PBDEs in GF conditions. Importantly, intestinal microbiome was necessary for PBDE-mediated decreases in branched chain and aromatic amino acid metabolites including 3-indolepropionic acid, a tryptophan metabolite recently shown to be protective against inflammation and diabetes. Gene-metabolite networks revealed a pos. association between the hepatic glycan synthesis gene alpha-1,6-mannosyltransferase (Alg12) mRNA and mannose which are important for protein glycosylation. Glycome changes have been observed in patients with metabolic syndrome. In LIC of CV mice, 23 bacterial taxa were regulated by PBDEs. Correlations of certain taxa with distinct serum metabolites further highlight a modulatory role of the microbiome in mediating PBDE effects. In summary, PBDEs impact intermediary metabolism in an intestinal microbiome-dependent manner, suggesting that dysbiosis may contribute to PBDE-mediated toxicities including metabolic syndrome.

Drug Metabolism & Disposition published new progress about Carnitines Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application In Synthesis of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Song, Bichao published the artcilePd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors, Related Products of isoquinoline, the main research area is vinylethylene carbonate diazo ester palladium decarboxylative olefination catalyst; vinyloxazolidinone diazo ester palladium decarboxylative olefination catalyst; vinylbenzoxazinone diazo ester palladium decarboxylative olefination catalyst; butadiene polysubstituted stereoselective preparation.

The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alc.-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.

Journal of the American Chemical Society published new progress about Allyl amines Role: SPN (Synthetic Preparation), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

He, Zhen published the artcileThe Interrupted Pummerer Reaction in a Sulfoxide-Catalyzed Oxidative Coupling of 2-Naphthols, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is interrupted Pummerer reaction sulfoxide catalyzed oxidative coupling naphthol; nigerone isonigerone synthesis; BINOLs; Pummerer reaction; metal-free catalysis; oxidative coupling; sulfoxide.

A benzothiophene S-oxide catalyst, generated in situ by sulfur oxidation with H2O2, mediates the oxidative coupling of 2-naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2-naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S-oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased in the synthesis of the bioactive natural products, (±)-nigerone (I) and (±)-isonigerone (II). Although Pummerer reactions are used widely, their application in catalysis is rare, and our approach represents a new catalytic manifold for metal-free C-C bond formation.

Angewandte Chemie, International Edition published new progress about Aromatization (as driving force for catalyst regeneration). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Recommanded Product: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Oboh, Edmund published the artcileOptimization of the Urea Linker of Triazolopyridazine MMV665917 Results in a New Anticryptosporidial Lead with Improved Potency and Predicted hERG Safety Margin, Quality Control of 104-01-8, the main research area is triazolo pyridazine derivative structure linker preparation cryptosporidiosis.

Cryptosporidiosis is caused by infection of the small intestine by Cryptosporidium parasites, resulting in severe diarrhea, dehydration, malabsorption, and potentially death. The only FDA-approved therapeutic is only partially effective in young children and ineffective for immunocompromised patients. Triazolopyridazine MMV665917 is a previously reported anti-Cryptosporidium screening hit with in vivo efficacy but suffers from modest inhibition of the hERG ion channel, which could portend cardiotoxicity. Herein, we describe our initial development of structure-activity relationships of this novel lead series with a particular focus on optimization of the piperazine-urea linker. We have discovered that piperazine-acetamide is a superior linker resulting in identification of SLU-2633, which has an EC50 of 0.17μM, an improved projected margin vs. hERG, prolonged pharmacokinetic exposure in small intestine, and oral efficacy in vivo with minimal systemic exposure. SLU-2633 represents a significant advancement toward the identification of a new effective and safe treatment for cryptosporidiosis.

Journal of Medicinal Chemistry published new progress about Coccidiostats. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Quality Control of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Giofre, Sabrina published the artcileEnantio- and Regioselective Palladium(II)-Catalyzed Dioxygenation of (Aza-)Alkenols, Name: 4-Methoxyphenylacetic acid, the main research area is morpholine enantioselective regioselective preparation; allyl azaalkenol oxycarbonylphenyl iodane palladium catalyst dioxygenation intamol cyclization; tetrahydro pyran enantioselective regioselective preparation; allylalkenol oxycarbonylphenyl iodane palladium catalyst dioxygenation intamol cyclization; Pd catalysis; alkene difunctionalizations; alkenols; dioxygenation; enantioselectivity; hypervalent iodine.

An oxidative Pd-catalyzed intra-intermol. dioxygenation of (aza-)alkenols were reported, with total regioselectivity. To study the stereoselectivity, different chiral ligands as well as different hypervalent-iodine compounds was compared. In particular, by using a C-6 modified pyridinyl-oxazoline (Pyox) ligand and hypervalent iodine bearing an aromatic ring, an excellent enantio- and diastereoselectivity was achieved.

Angewandte Chemie, International Edition published new progress about Aliphatic alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Name: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem