Category: pyridine-derivatives

Pan, Qi; Ping, Yuanyuan; Wang, Yifan; Guo, Ya; Kong, Wangqing published the artcile< Ni-Catalyzed Ligand-Controlled Regiodivergent Reductive Dicarbofunctionalization of Alkenes>, Formula: C13H15F3N2O, the main research area is nickel catalyzed ligand controlled regiodivergent reductive dicarbofunctionalization alkene; five six membered benzo fused lactam preparation alkene dicarbofunctionalization; cyclization cross coupling indoleone dihydroquinolinone preparation.

Transition-metal-catalyzed dicarbofunctionalization of alkenes involving intramol. Heck cyclization followed by intermol. cross-coupling has emerged as a powerful engine for building heterocycles with sterically congested quaternary carbon centers. However, only exo-cyclization/cross-coupling products can be obtained; endo-selective cyclization/cross-coupling has not been reported yet and still poses a formidable challenge. We herein report the first example of catalyst-controlled dicarbofunctionalization of alkenes for the regiodivergent synthesis of five- and six-membered benzo-fused lactams bearing all-carbon quaternary centers. Using a chiral Pyrox- or Phox-type bidentate ligand, 5-exo cyclization/cross-couplings proceed favorably to produce indole-2-ones in good yields with excellent regioselectivity and enantioselectivities (up to 98% ee). When C6-carboxylic acid-modified 2,2′-bipyridine was used as the ligand, 3,4-dihydroquinolin-2-ones were obtained in good yields through 6-endo-selective cyclization/cross-coupling processes. This transformation is modular and tolerant of a variety of functional groups. The ligand rather than the substrate structures precisely dictates the regioselectivity pattern. Moreover, the synthetic value of this regiodivergent protocol was demonstrated by the preparation of biol. relevant mols. and structural scaffolds.

Journal of the American Chemical Society published new progress about Alkenylation. 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Formula: C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Yao, Kun; Yuan, Qianjia; Qu, Xingxin; Liu, Yangang; Liu, Delong; Zhang, Wanbin published the artcile< Pd-catalyzed asymmetric allylic substitution cascade using α-(pyridin-1-yl)-acetamides formed in situ as nucleophiles>, Related Products of 581-47-5, the main research area is chiral piperidinyl amino acid enantioselective preparation.

Chiral piperidine-containing amino acid derivatives, e.g., I, were synthesized via Pd-catalyzed asym. allylic substitution cascade reaction of cinnamyl carbonates, chloroacetamides and substituted pyridines. In situ generated α-(pyridin-1-yl)-acetamides were used as nucleophiles in this cascade reaction. The products could be easily converted into potential bioactive compounds, unnatural chiral amino acids and dipeptides. Pd-catalyzed asym. allylic substitution cascade using α-(pyridin-1-yl)-acetamides formed in situ as nucleophiles.

Chemical Science published new progress about Amides Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 581-47-5 belongs to class pyridine-derivatives, and the molecular formula is C10H8N2, Related Products of 581-47-5.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ohmori, Junya; Kubota, Hirokazu; Shimizu-Sasamata, Masao; Okada, Masamichi; Sakamoto, Shuichi published the artcile< Novel α-Amino-3-hydroxy-5-methylisoxazole-4-propionate Receptor Antagonists: Synthesis and Structure-Activity Relationships of 6-(1H-Imidazol-1-yl)-7-nitro-2,3(1H,4H)-pyrido[2,3-b]pyrazinedione and Related Compounds>, Name: 2-Amino-3-nitro-6-picoline, the main research area is azaquinoxalinedione AMPA receptor antagonist structure activity; imidazolyl pyridopyrazinedione preparation AMPA receptor antagonist.

The authors have synthesized and evaluated azaquinoxalinediones for their activity in inhibiting [3H]AMPA binding from rat whole brain. It was found that the azaquinoxalinedione nucleus functions as a bioisostere for quinoxalinedione in AMPA receptor binding. The detailed structure-activity relationships of 6- and/or 7-substituted 2,3(1H,4H)-pyrido[2,3-b]pyrazinedione derivatives showed some differences in comparison with those of the corresponding substituted quinoxalinediones, including 6-(1H-imidazol-1-yl)-7-nitro-2,3(1H,4H)-quinoxalinedione (I) (YM90K). X-ray study showed that conformation of the 7-nitro group of I·HCl was nearly coplanar with the quinoxaline ring, whereas the 6-imidazol-1-yl group was rotated with respect to the aromatic ring. Binding studies indicated that the bulkiness of the 6-substituent on the pyridopyrazinediones may be responsible for the selectivity against the glycine site on the NMDA receptor. Among the azaquinoxalinediones tested, 6-(1H-imidazol-1-yl)-7-nitro-2,3(1H,4H)-pyrido[2,3-b]pyrazinedione (II) exhibited a combination of the best affinity to the AMPA receptor with a Ki value of 0.14 μM and selectivity against the glycine site (no affinity at 10 μM). In vivo, II also protected against sound-induced seizures in DBA/2 mice (min. ED, 10 mg/kg i.p.).

Journal of Medicinal Chemistry published new progress about Anticonvulsants. 21901-29-1 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Name: 2-Amino-3-nitro-6-picoline.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lamb, Claire J. C.; Nderitu, Bryan G.; McMurdo, Gemma; Tobin, John M.; Vilela, Filipe; Lee, Ai-Lan published the artcile< Auto-Tandem Catalysis: PdII-Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane-1,3-diones>, Category: pyridine-derivatives, the main research area is cyclopentanedione continuous flow preparation autocatalyzed dehydrogenation oxidative Heck coupling; aerobic oxidation; auto-tandem catalysis; one-pot synthesis; oxidative Heck; palladium.

A Pd(II) catalyst system has been used to successfully catalyze two mechanistically distinct reactions in a one-pot procedure: dehydrogenation of 2,2-disubstituted cyclopentane-1,3-diones and the subsequent oxidative Heck coupling. This auto-tandem catalytic reaction is applicable to both batch and continuous flow processes, with the latter being the first example of a tandem aerobic dehydrogenation/oxidative Heck in flow. In addition, a telescoped reaction involving enantioselective desymmetrization of the all-C quaternary center was successfully achieved.

Chemistry – A European Journal published new progress about Cyclopentanes Role: SPN (Synthetic Preparation), PREP (Preparation). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Patel, Harshkumar H.; Prater, Matthew B.; Squire, Scott O.; Sigman, Matthew S. published the artcile< Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers>, Quality Control of 1416819-91-4, the main research area is chiral allylic aryl ether preparation palladium catalyzed alkenylation; enantioselective palladium catalyzed alkenylation acyclic enol ether.

This report details a palladium-catalyzed process to access highly functionalized, optically active allylic aryl ethers. A number of electron-deficient alkenyl triflates underwent enantioselective and site-selective coupling with acyclic aryl enol ethers in the presence of a chiral palladium catalyst. This transform provides chiral allylic ether products in high yields and excellent enantiomeric ratios, furnishing a unique disconnection to incorporate heteroatoms at a stereocenter. Finally, the applicability of the products to target synthesis was demonstrated through the formation of a chiral allylic alc. and the generation of a flavone-inspired product.

Journal of the American Chemical Society published new progress about Alkenylation. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Quality Control of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Akiu, Mayuko; Tsuji, Takashi; Sogawa, Yoshitaka; Terayama, Koji; Yokoyama, Mika; Tanaka, Jun; Asano, Daigo; Sakurai, Ken; Sergienko, Eduard; Sessions, E. Hampton; Gardell, Stephen J.; Pinkerton, Anthony B.; Nakamura, Tsuyoshi published the artcile< Discovery of 1-[2-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-3-(pyridin-4-ylmethyl)urea as a potent NAMPT (nicotinamide phosphoribosyltransferase) activator with attenuated CYP inhibition>, Category: pyridine-derivatives, the main research area is nicotinamide phosphoribosyltransferase activator pyrazolyltriazolopyridine pyridinylmethyl urea; CYP inhibition; LogD; NAD(+); NAMPT activators; Triazolopyridines.

Nicotinamide phosphoribosyltransferase (NAMPT) catalyzes the rate-limiting step of the NAD+ salvage pathway. Since NAD+ plays a pivotal role in many biol. processes including metabolism and aging, activation of NAMPT is an attractive therapeutic target for treatment of diverse array of diseases. Herein, we report the continued optimization of novel urea-containing derivatives which were identified as potent NAMPT activators. Early optimization of HTS hits afforded compound 12 (I) , with a triazolopyridine core, as a lead compound CYP direct inhibition (DI) was identified as an issue of concern, and was resolved through modulation of lipophilicity to culminate in 1-[2-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-3-(pyridin-4-ylmethyl)urea (21, II), which showed potent NAMPT activity accompanied with attenuated CYP DI towards multiple CYP isoforms.

Bioorganic & Medicinal Chemistry Letters published new progress about Biological permeation. 3731-53-1 belongs to class pyridine-derivatives, and the molecular formula is C6H8N2, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Yu, Hsien-Cheng; Islam, Shahidul M.; Mankad, Neal P. published the artcile< Cooperative Heterobimetallic Substrate Activation Enhances Catalytic Activity and Amplifies Regioselectivity in 1,4-Hydroboration of Pyridines>, Application of C6H4F3N, the main research area is cooperative catalyst NHC copper iron half sandwich regioselective borylation; pyridine regioselective borylation cooperative copper iron imidazolylidene catalyst; dihydropyridine boronate preparation regioselective hydroboration pyridine cooperative bimetallic catalyst.

Regioselective 1,4-hydroboration of pyridine derivatives and quinoline with pinacolborane is catalyzed efficiently by the heterobinuclear catalyst, (IPr)CuFeCp(CO)2, at only 2 mol % loading, providing access to valuable 1,4-dihydropyridine (1,4-DHP) products. A variety of reactive functional groups are tolerated in the pyridine 3-position, and sufficient catalytic activity was obtained for reduction of sterically hindered cases such as 3,5-disubstituted pyridines and even 4-substituted pyridines. Mechanistic experiments indicate that the superior catalytic activity and 1,4-regioselectivity of the Cu/Fe heterobinuclear catalyst, compared to the corresponding mononuclear Cu catalyst, is derived from biphilic cooperativity of two key catalytic intermediates: electrophilic CpFe(CO)2(Bpin) activates the pyridine substrates toward regioselective nucleophilic addition by (IPr)CuH.

ACS Catalysis published new progress about Boronic acids, esters Role: PEP (Physical, Engineering or Chemical Process), RCT (Reactant), SPN (Synthetic Preparation), PROC (Process), RACT (Reactant or Reagent), PREP (Preparation). 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Application of C6H4F3N.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lopez Quezada, Landys; Li, Kelin; McDonald, Stacey L.; Nguyen, Quyen; Perkowski, Andrew J.; Pharr, Cameron W.; Gold, Ben; Roberts, Julia; McAulay, Kathrine; Saito, Kohta; Somersan Karakaya, Selin; Javidnia, Prisca Elis; Porras de Francisco, Esther; Amieva, Manuel Marin; Diaz, Sara Palomo; Mendoza Losana, Alfonso; Zimmerman, Matthew; Liang, Hsin-Pin Ho; Zhang, Jun; Dartois, Veronique; Sans, Stephanie; Lagrange, Sophie; Goullieux, Laurent; Roubert, Christine; Nathan, Carl; Aube, Jeffrey published the artcile< Dual-Pharmacophore Pyrithione-Containing Cephalosporins Kill Both Replicating and Nonreplicating Mycobacterium tuberculosis>, Electric Literature of 3811-73-2, the main research area is pyrithione containing cephalosporin Mycobacterium replication; antimycobacterial; cephalosporin; pyrithione; tuberculosis; β-lactamase.

The historical view of β-lactams as ineffective antimycobacterials has given way to growing interest in the activity of this class against Mycobacterium tuberculosis (Mtb) in the presence of a β-lactamase inhibitor. However, most antimycobacterial β-lactams kill Mtb only or best when the bacilli are replicating. Here, a screen of 1904 β-lactams led to the identification of cephalosporins substituted with a pyrithione moiety at C3′ that are active against Mtb under both replicating and nonreplicating conditions, neither activity requiring a β-lactamase inhibitor. Studies showed that activity against nonreplicating Mtb required the in situ release of the pyrithione, independent of the known class A β-lactamase, BlaC. In contrast, replicating Mtb could be killed both by released pyrithione and by the parent β-lactam. Thus, the antimycobacterial activity of pyrithione-containing cephalosporins arises from 2 mechanisms that kill mycobacteria in different metabolic states.

ACS Infectious Diseases published new progress about Blood plasma. 3811-73-2 belongs to class pyridine-derivatives, and the molecular formula is C5H4NNaOS, Electric Literature of 3811-73-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem