Category: 104-01-8

Bi, Tongyu published the artcileNatural scaffolds-inspired synthesis of CF3-substituted macrolides enabled by Rh-catalyzed C-H alkylation macrocyclization, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is trifluoromethyl macrolide preparation diastereoselective chemoselective antiinflammatory.

Inspired by the key scaffolds of rapamycin and FR252921, a Rh(III)-catalyzed C-H alkylation macrocyclization, which enables access to CF3-substituted macrolides, is reported. DFT calculations revealed that the chemoselectivity between C-H alkylation and olefination macrocyclization is highly controllable. Moreover, the unique CF3-substituted macrolides showed potent anti-inflammation activities against TNF-α, IL-6 and CCL2 mRNA expression.

Chinese Chemical Letters published new progress about Alkylation catalysts (chemoselective). 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

Lin, Hua-Chen published the artcileA Pd-H/Isothiourea Cooperative Catalysis Approach to anti-Aldol Motifs: Enantioselective α-Alkylation of Esters with Oxyallenes, Formula: C9H10O3, the main research area is oxyallene pentafluorophenyl acetate palladium benzotetramisole enantioselective diastereoselective alkylation; pentafluorophenyl oxypentenoate preparation; methyl oxy butenyl carbamate preparation; Allenes; C1-Ammonium Enolates; Enantioselectivity; Isothioureas; Palladium Catalysis.

To complement the array of substrate-based strategies, and regulate enolate geometry at the catalyst level, a direct catalytic alkylation of esters with oxyallenes was developed. Synergizing metal hydride reactivity with Lewis base catalysis resulted in a broad reaction scope with useful levels of stereocontrol (up to >99% ee). Facile derivatization of these ambiphilic linchpins was demonstrated, providing access to high-value vicinal stereocenter-containing motifs, including 1,2-amino alcs.

Angewandte Chemie, International Edition 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, Formula: C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Arokianathar, Jude N. published the artcileIsothiourea-Catalyzed Enantioselective α-Alkylation of Esters via 1,6-Conjugate Addition to para-Quinone Methides, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is alkylated ester enantioselective diastereoselective preparation; nitrophenyl ester isothiourea catalyzed enantioselective alkylation para quinone methide; 1,6-conjugate addition; ammonium enolate; aryloxide; ester functionalization; isothiourea; quinone methide.

The isothiourea-catalyzed enantioselective 1,6-conjugate addition of para-nitrophenyl esters to 2,6-disubstituted para-quinone methides was reported. Para-nitrophenoxide, generated in situ from initial N-acylation of the isothiourea by the para-nitrophenyl ester, was proposed to facilitate catalyst turnover in this transformation. A range of para-nitrophenyl ester products could be isolated, or derivatized in situ by addition of benzylamine to give amides at up to 99% yield. Although low diastereocontrol was observed, the diastereoisomeric ester products were separable and formed with high enantiocontrol (up to 94:6 er).

Molecules 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

Chen, Hongyu published the artcileData-driven catalyst optimization for stereodivergent asymmetric synthesis by iridium/boron hybrid catalysis, Application In Synthesis of 104-01-8, the main research area is allylic carboxylic acid stereodivergent enantioselective regioselective chemoselective diastereoselective preparation; carboxylic acid stereodivergent enantioselective allylation iridium boron hybrid catalysis.

Here, the straightforward identification of asym. two-component iridium/boron hybrid catalyst systems for α-C-allylation of carboxylic acids was reported. Structural optimization of the chiral ligands for iridium catalysts was driven by mol.-field-based regression anal. with a dataset containing overall 32 mol. structures. The catalyst systems enabled selective access to all the possible isomers of chiral carboxylic acids bearing contiguous stereocenters. This chemoselective and stereodivergent, asym. catalysis was applicable to late-stage structural modifications of drugs and their derivatives

Cell Reports Physical Science published new progress about Allylation catalysts, stereoselective. 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

Mak, Jeffrey Y. W. published the artcileHDAC7 Inhibition by Phenacetyl and Phenylbenzoyl Hydroxamates, Application of 4-Methoxyphenylacetic acid, the main research area is HDAC7 inhibitors catalytic site phenylbenzoyl hydroxamates phthalimide stability solubility.

The zinc-containing histone deacetylase enzyme HDAC7 is emerging as an important regulator of immunometabolism and cancer. Here, we exploit a cavity in HDAC7, filled by Tyr303 in HDAC1, to derive new inhibitors. Phenacetyl hydroxamates and 2-phenylbenzoyl hydroxamates bind to Zn2+ and are 50-2700-fold more selective inhibitors of HDAC7 than HDAC1. Phenylbenzoyl hydroxamates are 30-70-fold more potent HDAC7 inhibitors than phenacetyl hydroxamates, which is attributed to the benzoyl aromatic group interacting with Phe679 and Phe738. Phthalimide capping groups, including a saccharin analog, decrease rotational freedom and provide hydrogen bond acceptor carbonyl/sulfonamide oxygens that increase inhibitor potency, liver microsome stability, solubility, and cell activity. Despite being the most potent HDAC7 inhibitors to date, they are not selective among class IIa enzymes. These strategies may help to produce tools for interrogating HDAC7 biol. related to its catalytic site.

Journal of Medicinal Chemistry published new progress about Drug metabolism (metabolic stability). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application of 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Lee, Jisook published the artcileNovel Human Aminopeptidase N Inhibitors: Discovery and Optimization of Subsite Binding Interactions, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is microsomal aminopeptidase N hydroxamic acid.

Aminopeptidase N (APN/CD13) is a zinc-dependent M1 aminopeptidase that contributes to cancer progression by promoting angiogenesis, metastasis, and tumor invasion. We have previously identified hydroxamic acid-containing analogs that are potent inhibitors of the APN homolog from the malarial parasite Plasmodium falciparum M1 aminopeptidase (PfA-M1). Herein, we describe the rationale that underpins the repurposing of PfA-M1 inhibitors as novel APN inhibitors. A series of novel hydroxamic acid analogs were developed using a structure-based design approach and evaluated their inhibition activities against APN. N-(2-(Hydroxyamino)-2-oxo-1-(3′,4′,5′-trifluoro-[1,1′-biphenyl]-4-yl)ethyl)-4-(methylsulfonamido)benzamide (6ad) proved to be an extremely potent inhibitor of APN activity in vitro, selective against other zinc-dependent enzymes such as matrix metalloproteases, and possessed limited cytotoxicity against Ad293 cells and favorable physicochem. and metabolic stability properties. The combined results indicate that compound 6ad may be a useful lead for the development of anticancer agents.

Journal of Medicinal Chemistry published new progress about Drug metabolism (metabolic stability). 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

Zhao, Yunbo published the artcileB(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is diazoacetate benzotriazole pentafluorophenyl borane catalyst regioselective alkylation; alkyl benzotriazole preparation.

Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes was described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-alkylated benzotriazoles in good to excellent yields and this protocol was successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.

Chemical Communications (Cambridge, United Kingdom) published new progress about Alkylation catalysts, regioselective. 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

Henry, Martyn C. published the artcileOne-pot ortho-amination of aryl C-H bonds using consecutive iron and copper catalysis, Formula: C9H10O3, the main research area is arene nucleophile regioselective amination bond activation iron copper catalyst.

A one-pot approach for ortho-coupling of arenes with non-activated N-nucleophiles has been developed using sequential iron and copper catalysis. Regioselective ortho-activation of anisoles such as p-phenylanisole, 4-methoxyanisole, 3,4-dimethylanisole, etc. anilines such as 4-aminobenzonitrile, 4-nitroaniline, 4-methylaniline, etc. and p-cresol was achieved through iron(III) triflimide catalyzed iodination, followed by a copper(I)-catalyzed, ligand-assisted coupling reaction with N-heterocycle such as pyrazole, imidazole, pyrrole, 2-pyrrolidinone, amides such as benzamide, p-toluamide and sulfonamide-based nucleophiles such as benzenesulfonamide, p-toluenesulfonamide, p-chlorobenzenesulfonamide, methanesulfonamide. The synthetic utility of this one-pot, two-step method for the direct amination of ortho-aryl C-H bonds was demonstrated with the late-stage functionalization of 7-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one. This allowed the preparation of a TRIM24 bromodomain inhibitor I [R = C6H5S(O)2NH] and a series of novel analogs I [R = C6H5C(O)NH, 2-oxopyrrolidin-1-yl, 1H-pyrazol-1-yl, etc.].

Organic & Biomolecular Chemistry published new progress about Amination catalysts (regioselective). 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

Yuan, Yu-Chao published the artcileEnantiopure isothiourea@carbon-based support: stacking interactions for recycling a lewis base in asymmetric catalysis, HPLC of Formula: 104-01-8, the main research area is chiral isothiourea functionalized pyrene preparation; oxazolidinone oxaziridine arylacetic anhydride isothiourea Lewis base asym catalysis.

The synthesis of a chiral isothiourea (hyperBTM) I functionalized by a pyrene moiety was described via click chem. This new enantiopure Lewis base was used as supported catalyst thanks to its immobilization on reduced graphene oxide via strong π-π interactions between the polyaromatic core and the carbon support. The synthesis of scalemic oxazolidin-4-ones II [Ar = Ph, 2-naphthyl, 4-FPh, 4-MeOPh] from oxaziridines and arylacetic anhydrides was chosen as a test reaction to assess the validity of the process, this transformation having never been carried out under recycling conditions. Optimization of the reaction conditions led to the synthesis of the targeted products in high yields and good to excellent enantioselectivity values with the supported catalyst. Recovery of the active species occurred by simple filtration, the immobilized catalyst was then successfully reengaged in seven consecutive cycles while maintaining its efficiency. The robustness of this chiral organic isothiourea was also demonstrated in an original multi-substrate procedure.

Organic Chemistry Frontiers published new progress about [3+2] Cycloaddition reaction, stereoselective. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, HPLC of Formula: 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Ye, Chen-Xi published the artcileStereocontrolled 1,3-nitrogen migration to access chiral α-amino acids, Application In Synthesis of 104-01-8, the main research area is chiral amino acid preparation regioselective enantioselective; azanyl ester preparation amination ruthenium iron catalyst; carboxylic acid hydroxylamine coupling reaction.

Here a protocol for the economical and practical synthesis of optically active α-amino acids RNHC(R1)(R2)C(O)OH (R = Ts, Ms, C(O)OMe, (2,2,2-trichloroethoxy)carbonyl; R1 = H, Me; R2 = pent-2-yn-1-yl, 4-methylphenyl, 2H-1,3-benzodioxol-5-yl, etc.) based on an unprecedented stereocontrolled 1,3-nitrogen shift was reported. The method employs abundant and easily accessible carboxylic acids R1CH(R2)C(O)OH as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalyzed C(sp3)-H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products.

Nature Chemistry published new progress about Amination catalysts (regio-, stereoselective). 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