Category: pyridine-derivatives

Silva, Allan R.; Polo, Ellen C.; Martins, Nelson C.; Correia, Carlos Roque D. published the artcile< Enantioselective Oxy-Heck-Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (-)-Conocarpan>, Computed Properties of 1416819-91-4, the main research area is aryldiazonium salt styrenic olefin palladium Oxy Heck Matsuda arylation; dihydrobenzofuran stereoselective preparation.

This work discloses the first examples of an effective enantioselective oxy-Heck-Matsuda reaction using a variety of styrenic olefins to generate chiral dihydrobenzofurans I (R1 = 6-NO2, 5-NO2, 5-Me, etc.; R2 = 4-OMe, 4-OH, 2,4-OMe, etc.; R3 = Me, i-Pr). The reaction proceeds in moderate to good yields, with high trans diastereoselectivity (up to 20:1) in enantioselectivities up to 90:10 using the N,N-ligand pyrimidine-bisoxazoline (PyriBox). The oxy-Heck-Matsuda reactions were carried out under mild conditions and rather low catalyst loadings. The feasibility and practicality of the process is demonstrated by a concise total synthesis of the neolignan (-)-conocarpan. X-ray diffraction of an advanced brominated intermediate in the route to (-)-conocarpan has allowed the unequivocal assignment of the absolute stereochem. of the oxy-Heck-Matsuda aryldihydrobenzofuran products. A rationale for the mechanism operating in these enantioselective oxy-Heck-Matsuda reactions is also presented.

Advanced Synthesis & Catalysis published new progress about Benzofurans Role: SPN (Synthetic Preparation), PREP (Preparation) (Dihydro). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Computed Properties of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Heusler, Arne; Fliege, Julian; Wagener, Tobias; Glorius, Frank published the artcile< Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines>, Electric Literature of 3796-23-4, the main research area is dihydropyridine preparation regioselective; pyridine triflic anhydride dearomatization trimethylamine borane; phenyl chloroformate pyridine dearomatization trimethylamine borane; boranes; chemoselectivity; nitrogen heterocycles; reduction; synthetic methods.

The synthesis of a broad variety of N-substituted 1,4-dihydropyridines I [R = H, 3-Me, 3,5-di-Br, etc.; R1 = Tf, CO2Ph] and 1,2-dihydropyridines II [R2 = F, Cl, CF3, Ph, SPh; R3 = H, F, trimethylsilyl] by very mild and selective reduction with amine borane was reported for the first time.

Angewandte Chemie, International Edition published new progress about Dearomatization. 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Electric Literature of 3796-23-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Anson, Francesca; Thayumanavan, S.; Hardy, Jeanne A. published the artcile< Exogenous Introduction of Initiator and Executioner Caspases Results in Different Apoptotic Outcomes>, Recommanded Product: 1,2-Di(pyridin-2-yl)disulfane, the main research area is initiator executioner caspase apoptosis.

The balance of pro-apoptotic and pro-survival proteins defines a cell′s fate. These processes are controlled through an interdependent and finely tuned protein network that enables survival or leads to apoptotic cell death. The caspase family of proteases is central to this apoptotic network, with initiator and executioner caspases, and their interaction partners, regulating and executing apoptosis. In this work, we interrogate and modulate this network by exogenously introducing specific initiator or executioner caspase proteins. Each caspase is exogenously introduced using redox-responsive polymeric nanogels. Although caspase-3 might be expected to be the most effective due to the centrality of its role in apoptosis and its heightened catalytic efficiency relative to other family members, we observed that caspase-7 and caspase-9 are the most effective at inducing apoptotic cell death. By critically analyzing the introduced activity of the delivered caspase, the pattern of substrate cleavage, as well as the ability to activate endogenous caspases, we conclude that the efficacy of each caspase correlated with the levels of pro-survival factors that both directly and indirectly impact the introduced caspase. These findings lay the groundwork for developing methods for exogenous introduction of caspases as a therapeutic option that can be tuned to the apoptotic balance in a proliferating cell.

JACS Au published new progress about Apoptosis. 2127-03-9 belongs to class pyridine-derivatives, and the molecular formula is C10H8N2S2, Recommanded Product: 1,2-Di(pyridin-2-yl)disulfane.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Robinson, Donovan J.; Ortiz, Kacey G.; O’Hare, Nathan P.; Karimov, Rashad R. published the artcile< Dearomatization of Heteroarenium Salts with ArBpin Reagents. Application to the Total Synthesis of a Nuphar Alkaloid>, Name: 3-(Methoxycarbonyl)pyridine, the main research area is carbonylpyridinium triflate arylboron pinacol ester rhodium catalyst enantioselective dearomatization; aryl dihydropyridinecarboxylate preparation; Nuphar alkaloid preparation.

Rhodium-catalyzed enantioselective addition of aryl and heteroaryl boron pinacol esters to pyridinium and quinolinium salts were developed for the synthesis of enantioenriched dihydroheteroarenes. The methodol. was enabled the synthesis of 2-heteroaryl-substituted dihydropyridines in high yield and ee, which provided efficient synthetic access to a nuphar alkaloid.

Organic Letters published new progress about Aromatic esters Role: RCT (Reactant), RACT (Reactant or Reagent). 93-60-7 belongs to class pyridine-derivatives, and the molecular formula is C7H7NO2, Name: 3-(Methoxycarbonyl)pyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Gurgul, Ilona; Mazuryk, Olga; Lomzik, Michal; Gros, Philippe C.; Rutkowska-Zbik, Dorota; Brindell, Malgorzata published the artcile< Unexplored features of Ru(II) polypyridyl complexes - towards combined cytotoxic and antimetastatic activity>, Synthetic Route of 366-18-7, the main research area is cytotoxicity antimetastatic polypyridyl Ru II.

Therefore, scientists have to concentrate their efforts on designing compounds affecting not only the primary tumor, but also efficiently inhibiting metastasis. Herein, we report two families of Ru(II) polypyridyl complexes bearing 2,2′-bipyridine substituted by a semicarbazone 2-formylopyridine moiety as one of the ligands and 4,4′-di-tert-butyl-2,2′-dipyridyl or 4,7-diphenyl-1,10-phenanthroline as auxiliary ligands. These complexes strengthen cells’ adherent properties and inhibit the activity of metalloproteinases (MMPs) in vitro, which is relevant in anti-metastatic treatment. The in vitro studies were performed on human lung adenocarcinoma (A549) and human pancreatic cancer (PANC-1) cells, which have a well-documented invasive potential. The induced alteration of the tumor cells’ adhesion properties correlated with the high cytotoxic effect exerted by the complexes and their excellent cellular uptake. It was also proved that both complexes directly inhibit M-MP2 and M-MP9 enzyme activities, which are essential for the development of tumor metastasis. The results of this study indicate that the biol. properties of polypyridyl Ru(II) complexes extend beyond the standard cytotoxic activity and represent an important step towards designing new anti-metastatic agents.

Metallomics published new progress about Cytotoxicity. 366-18-7 belongs to class pyridine-derivatives, and the molecular formula is C10H8N2, Synthetic Route of 366-18-7.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ladduwahetty, Tammy; Lee, Matthew R.; Maillard, Michel C.; Cachope, Roger; Todd, Daniel; Barnes, Michael; Beaumont, Vahri; Chauhan, Alka; Gallati, Caroline; Haughan, Alan F.; Kempf, Georg; Luckhurst, Christopher A.; Matthews, Kim; McAllister, George; Mitchell, Philip; Patel, Hiral; Rose, Mark; Saville-Stones, Elizabeth; Steinbacher, Stefan; Stott, Andrew J.; Thatcher, Emma; Tierney, Jason; Urbonas, Liudvikas; Munoz-Sanjuan, Ignacio; Dominguez, Celia published the artcile< Identification of a Potent, Selective, and Brain-Penetrant Rho Kinase Inhibitor and its Activity in a Mouse Model of Huntington's Disease>, Quality Control of 870997-85-6, the main research area is piperazine analog preparation Rho kinase inhibitor SAR docking pharmacokinetics.

The Rho kinase (ROCK) pathway is implicated in the pathogenesis of several conditions, including neurol. diseases. In Huntington’s disease (HD), ROCK is implicated in mutant huntingtin (HTT) aggregation and neurotoxicity, and members of the ROCK pathway are increased in HD mouse models and patients. To validate this mode of action as a potential treatment for HD, a potent, selective, central nervous system (CNS)-penetrant ROCK inhibitor was sought. Identifying a compound that could be dosed orally in mice with selectivity against other AGC kinases, including protein kinase G (PKG), whose inhibition could potentially activate the ROCK pathway, was paramount for the program. The optimization of published ligands to identify a novel series of ROCK inhibitors based on a piperazine core was demonstrated. Morphing of the early series developed inhouse by scaffold hopping enabled the identification of a compound exhibiting high potency and desired selectivity and demonstrating a robust pharmacodynamic (PD) effect by the inhibition of ROCK-mediated substrate (MYPT1) phosphorylation after oral dosing.

Journal of Medicinal Chemistry published new progress about Molecular docking. 870997-85-6 belongs to class pyridine-derivatives, and the molecular formula is C6H5BrN2O2, Quality Control of 870997-85-6.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Beak, Peter; Covington, Johnny B.; Smith, Stanley G.; White, J. Matthew; Zeigler, John M. published the artcile< Displacement of protomeric equilibriums by self-association: hydroxypyridine-pyridone and mercaptopyridine-thiopyridone isomer pairs>, COA of Formula: C5H4ClNO, the main research area is tautomerism pyridinol pyridinethiol association; solvent effect association pyridinol.

Self-association and protomeric equilibrium constants are reported for 2-hydroxypyridine-2-pyridone, 4-hydroxypyridine-4-pyridone and 2-mercaptopyridine-2-thiopyridone isomer pairs in different solvents. These results provide quant. evidence for significant differences in the positions of protomeric equilibrium for self-associated and monomeric species. The 2-substituted isomers are associated as well-known dimers while the 4-substituted systems form oligomers. In polar and H-bonding solvents self-association is substantially reduced. Sterically hindered 2- and 4-pyridones are less associated than unhindered systems. These results imply that determinations and interpretations of protomeric equilibrium should take into account the possible dominance of self-association

Journal of Organic Chemistry published new progress about Self-association. 73018-09-4 belongs to class pyridine-derivatives, and the molecular formula is C5H4ClNO, COA of Formula: C5H4ClNO.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhang, Keping; Ding, Chengqiang; Liu, Xiaolin; Gao, Jun; Wu, Datong; Qin, Yong; Kong, Yong published the artcile< A redox and pH dual-triggered drug delivery platform based on chitosan grafted tubular mesoporous silica>, Recommanded Product: 1,2-Di(pyridin-2-yl)disulfane, the main research area is chitosan tubular mesoporous silica hydrogen ion concentration drug delivery.

Tubular mesoporous silica (T-mSiO2) was facilely synthesized through a co-template method by using cetyltrimethylammonium bromide and α-Fe2O3 as the dual templates, and then disulfide (-SS-) bonds and carboxyl groups (-COOH) were introduced to the resultant T-mSiO2 via the reaction with 2-carboxyethyl 2-pyridyl disulfide. The obtained -SS- grafted T-mSiO2 (SS-T-mSiO2) was then grafted with chitosan (CS) via the amidation reaction between the -COOH groups on SS-T-mSiO2 and the -NH2 groups on CS. The CS grafted SS-T-mSiO2 (CS-SS-T-mSiO2) was fully characterized by various technologies such as transmission electron microscopy, energy dispersive X-ray spectroscopy and Fourier transform IR spectroscopy. Finally, the as-synthesized CS-SS-T-mSiO2 was used as the carrier for redox and pH dual-triggered delivery of 5-fluorouracil (5-FU), an anti-cancer drug, and the results indicate that the developed CS-SS-T-mSiO2 might be a potential responsive carrier for redox and pH dual-triggered drug delivery.

Ceramics International published new progress about Amidation. 2127-03-9 belongs to class pyridine-derivatives, and the molecular formula is C10H8N2S2, Recommanded Product: 1,2-Di(pyridin-2-yl)disulfane.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Liu, Ruiting; Tzounopoulos, Thanos; Wipf, Peter published the artcile< Synthesis and Optimization of Kv7 (KCNQ) Potassium Channel Agonists: The Role of Fluorines in Potency and Selectivity>, Formula: C7H7F3N2, the main research area is KCNQ potassium channel agonist preparation structure.

Based on the potent Kv7 agonist RL-81, we prepared new lead structures with greatly improved selectivity for Kv7.2/Kv7.3 over related potassium channels, i.e., Kv7.3/Kv7.5, Kv7.4, and Kv7.4/7.5. RL-36 and RL-12 maintain an agonist EC2x of ca. 1 μM on Kv7.2/Kv7.3 in a high-throughput assay on an automated electrophysiol. platform in HEK293 cells but lack activity on Kv7.3/Kv7.5, Kv7.4, and Kv7.4/7.5, resulting in a selectivity index SI > 10. RL-56 is remarkably potent, EC2x 0.11 ± 0.02 μM, and still shows an SI = 2.5. We also identified analogs with significant selectivity for Kv7.4/Kv7.5 over Kv7.2/Kv7.3. The extensive use of fluorine in iterative core structure modifications highlights the versatility of these substituents, including F, CF3, and SF5, to span orders of magnitude of potency and selectivity in medicinal chem. lead optimizations.

ACS Medicinal Chemistry Letters published new progress about Homo sapiens. 387350-39-2 belongs to class pyridine-derivatives, and the molecular formula is C7H7F3N2, Formula: C7H7F3N2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Potapov, V. A.; Ishigeev, R. S.; Shkurchenko, I. V.; Amosova, S. V. published the artcile< Assembling of Thiazolo[3,2-a]pyridinium Salts via the Reaction of 2-Pyridinesulfenyl Halides with Vinyl Ethyl Ether>, Category: pyridine-derivatives, the main research area is pyridinesulfenyl halide vinyl ethyl ether regioselective heterocyclization; ethoxy thiazolopyridinum halide preparation.

The regio- and stereoselective synthesis of 3-ethoxy-2H,3H-[1,3]thiazolo[3,2-a]pyridin-4-ium halides via the reaction of 2-pyridinesulfenyl halides with vinyl Et ether was elaborated.

Russian Journal of General Chemistry published new progress about Ethers Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 2127-03-9 belongs to class pyridine-derivatives, and the molecular formula is C10H8N2S2, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem