Day: December 5, 2022

Song, Peidong published the artcileDevelopment of a Tunable Chiral Pyridine Ligand Unit for Enantioselective Iridium-Catalyzed C-H Borylation, Related Products of pyridine-derivatives, the publication is ACS Catalysis (2021), 11(12), 7339-7349, database is CAplus.

Although pyridine derivatives are versatile supporting ligands in catalysis, the development of their chiral versions has been relatively limited. Herein, we report the design, synthesis, and proof-of-concept application of a structurally tunable chiral pyridine framework featuring an annulated compact ring system. Using an N,B-bidentate ligand skeleton containing the chiral pyridine moiety, we have developed an enantioselective iridium-catalyzed desymmetrizing C-H borylation reaction of diaryl(2-pyridyl)methane compounds with up to 96% ee and 93% yield. The resulting borylation products could be readily transformed into various chiral tri(hetero)arylmethane compounds D. functional theory investigations revealed that the two chair conformations of the flexible ketal motif both favored the enantiomer that was consistent with exptl. results. This work has thus introduced an effective and tunable chiral pyridine ligand framework that may be used in many catalytic asym. transformations.

ACS Catalysis published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C9H5ClO2, Related Products of pyridine-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Wu, Zhibing published the artcileSynthesis and antifungal activity of N-(substituted pyridinyl)-1-methyl(phenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives, Computed Properties of 18437-58-6, the publication is Molecules (2012), 14205-14218, database is CAplus and MEDLINE.

A series of 1-methyl- and 1-phenyl-N-pyridinyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamides was synthesized. All target compounds were bioassayed in vitro against of phytopathogenic fungi (Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica). Some of the compounds exhibited moderate antifungal activities, among which three of the compounds displayed >50% inhibition against G. zeae at 100 μg/mL, which was better than that of the com. fungicides carboxin and boscalid.

Molecules published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C9H6N2O2, Computed Properties of 18437-58-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Latli, Bachir published the artcilePotent and selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1 labeled with carbon-13 and carbon-14, Recommanded Product: (1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)boronic acid, the publication is Journal of Labelled Compounds and Radiopharmaceuticals (2017), 60(9), 420-430, database is CAplus and MEDLINE.

(S)-6-(2-Hydroxy-2-methylpropyl)-3-((S)-1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (I) and (4aR,9aS)-1-(1H-benzo[d]midazole-5-carbonyl)-2,3,4,4a,9,9a-hexahydro-1-H-indeno[2,1-b]pyridine-6-carbonitrile hydrochloride (II) are potent and selective inhibitor of 11β-hydroxysteroid dehydrogenase type 1 enzyme. These 2 drug candidates developed for the treatment of type-2 diabetes were prepared labeled with carbon-13 and carbon-14 to enable drug metabolism, pharmacokinetics, bioanal., and other studies. In the carbon-13 synthesis, benzoic-¹³C₆ acid was converted in 7 steps and in 16% overall yield to [¹³C₆]-I. Aniline-¹³C₆ was converted in 7 steps to 1H-benzimidazole-1-2,3,4,5,6-¹³C₆-5-carboxylic acid and then coupled to a tricyclic chiral indenopiperidine to afford [¹³C₆]-II in 19% overall yield. The carbon-14 labeled I was prepared efficiently in 2 radioactive steps in 41% overall yield from an advanced intermediate using carbon-14 labeled Me magnesium iodide and Suzuki-Miyaura cross coupling via in situ boronate formation. As for the synthesis of [¹⁴C]-II, 1H-benzimidazole-5-carboxylic-¹⁴C acid was first prepared in 4 steps using potassium cyanide-¹⁴C, then coupled to the chiral indenopiperidine using amide bond formation conditions in 26% overall yield.

Journal of Labelled Compounds and Radiopharmaceuticals published new progress about 1351413-50-7. 1351413-50-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Amide,Pyridine,Boronic Acids,Boronic acid and ester, name is (1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)boronic acid, and the molecular formula is C6H8BNO3, Recommanded Product: (1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Barnett, Kerry L. published the artcileAir-Stable [(R₃P)PdCl₂]₂ Complexes of Neopentylphosphines as Cross-Coupling Precatalysts: Catalytic Application and Mechanism of Catalyst Activation and Deactivation, Recommanded Product: 2-Pyridinylboronic acid, the publication is Organometallics (2018), 37(9), 1410-1424, database is CAplus.

Air-stable [(R₃P)PdCl₂]₂ complexes with di-tert-butylneopentylphosphine (DTBNpP, 1a) or trineopentylphosphine (TNpP, 1b) ligands were applied to Suzuki cross-coupling reactions, and the mechanism of their conversion to the active LPd(0) catalyst species was studied. Precatalysts 1a,b provide effective catalysts for Suzuki cross-coupling of aryl bromides at room temperature, even when the reactions were performed in air. The precatalyst systems provided much higher activity catalysts in toluene/H₂O in comparison to MeCN/H₂O. Precatalyst loadings could be decreased by a factor of 50 in toluene in comparison to MeCN, while achieving equal or better yields. In MeCN/H₂O, ligand metalation to form a [(κ²-P,C-DTBNpP)PdX]₂ palladacycle was found to compete with formation of the active Pd(0) species. The palladacycle shows low catalytic activity; thus, its formation represents a catalyst deactivation pathway. In toluene, clean formation of the active Pd(0) species occurs without competitive palladacycle formation. The improved selectivity to form the active Pd(0) species in toluene appears to account for the higher activity of the precatalysts in toluene/H₂O.

Organometallics published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C5H6BNO2, Recommanded Product: 2-Pyridinylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Ju, Han published the artcileIterative Optimization and Structure-Activity Relationship Studies of Oseltamivir Amino Derivatives as Potent and Selective Neuraminidase Inhibitors via Targeting 150-Cavity, COA of Formula: C5H6BNO2, the publication is Journal of Medicinal Chemistry (2022), 65(17), 11550-11573, database is CAplus and MEDLINE.

With our continuous endeavors in seeking neuraminidase (NA) inhibitors, we reported herein three series of novel oseltamivir amino derivatives with the goal of exploring the druggable chem. space inside the 150-cavity of influenza virus NAs. Among them, around half of the compounds in series C were demonstrated to be better inhibitors against both wild-type and oseltamivir-resistant group-1 NAs than oseltamivir carboxylate (OSC). Notably, compounds 12d, 12e, 15e, and 15i showed more potent or equipotent antiviral activity against H1N1, H5N1, and H5N8 viruses compared to OSC in cellular assays. Furthermore, compounds 12e and 15e exhibited high metabolic stability in human liver microsomes (HLMs) and low inhibitory effect on main cytochrome P 450 (CYP) enzymes, as well as low acute/subacute toxicity and certain antiviral efficacy in vivo. Also, pharmacokinetic (PK) and mol. docking studies were performed. Overall, 12e (I) and 15e (II) possess great potential to serve as anti-influenza candidates and are worthy of further investigation.

Journal of Medicinal Chemistry published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C5H6BNO2, COA of Formula: C5H6BNO2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Allegretti, Paul A. published the artcileGeneration of highly potent DYRK1A-dependent inducers of human β-Cell replication via Multi-Dimensional compound optimization, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid, the publication is Bioorganic & Medicinal Chemistry (2020), 28(1), 115193, database is CAplus and MEDLINE.

Small mol. stimulation of β-cell regeneration has emerged as a promising therapeutic strategy for diabetes. Although chem. inhibition of dual specificity tyrosine-phosphorylation-regulated kinase 1A (DYRK1A) is sufficient to enhance β-cell replication, current lead compounds have inadequate cellular potency for in vivo application. Herein, we report the clin. stage anti-cancer kinase inhibitor OTS167 as a structurally novel, remarkably potent DYRK1A inhibitor and inducer of human β-cell replication. Unfortunately, OTS167’s target promiscuity and cytotoxicity curtails utility. To tailor kinase selectivity towards DYRK1A and reduce cytotoxicity we designed a library of fifty-one OTS167 derivatives based upon a modeled structure of the DYRK1A-OTS167 complex. Indeed, derivative characterization yielded several leads with exceptional DYRK1A inhibition and human β-cell replication promoting potencies but substantially reduced cytotoxicity. These compounds are the most potent human β-cell replication-promoting compounds yet described and exemplify the potential to purposefully leverage off-target activities of advanced stage compounds for a desired application.

Bioorganic & Medicinal Chemistry published new progress about 903899-13-8. 903899-13-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Alcohol,Boronic Acids,Boronic acid and ester, name is (6-Hydroxypyridin-3-yl)boronic acid, and the molecular formula is C5H6BNO3, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Hassan, Mirja Mahamudul Md published the artcileIridium-Catalyzed Site-Selective Borylation of 8-Arylquinolines, SDS of cas: 85237-71-4, the publication is Synthesis (2021), 53(18), 3333-3342, database is CAplus.

The authors report a convenient method for the highly site-selective borylation of 8-arylquinoline. The reaction proceeds smoothly in the presence of a catalytic amount of [Ir(OMe)(cod)]₂ and 2-phenylpyridine derived ligand using bis(pinacolato)diborane as the borylating agent. The reactions occur with high selectivity with many functional groups, providing borylated 8-aryl quinolines with good to excellent yield and excellent selectivity. The borylated compounds formed in this method can be transformed into various important synthons by using known transformations.

Synthesis published new progress about 85237-71-4. 85237-71-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is 5-Methyl-2-(p-tolyl)pyridine, and the molecular formula is C13H13N, SDS of cas: 85237-71-4.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Renaud, Justin B. published the artcileNormalization of LC-MS mycotoxin determination using the N-alkylpyridinium-3-sulfonates (NAPS) retention index system, Category: pyridine-derivatives, the publication is Journal of Chromatography A (2021), 461901, database is CAplus and MEDLINE.

A major challenge for LC-MS anal. is the ability to compare data between laboratories and across instrument platforms. Currently, mycotoxin determination relies on dereplication strategies based on physicochem. properties such as the m/z of the precursor and product ions. Unlike these intrinsic properties, retention time (tR) is an extrinsic property impacted by LC conditions, including mobile phases and column chem., making exchange of data between groups difficult. To address this, we are introducing the concept of incorporating an electrospray compatible, retention index (RI) system based on a series of N-alkylpyridinium-3-sulfonates (NAPS) into routine mycotoxin determination These standards of differing alkyl chain length span RI units from 100 to 2000, are UV active and have fixed pos. and neg. charges for electrospray ionization in either mode. Using high resolution LC-MS/MS, the RIs of 96 mycotoxins and fungal secondary metabolites were normalized as a proof of concept with the NAPS RI system under multiple pH, column and gradient chromatog. conditions. This method was then applied to the anal. of a crude extract of Penicillium roqueforti, where we were able to decrease the number of false positives by implementing an RI filter as well as a secondary correction factor. Addnl., we developed software that allows users to convert published RIs to a predicted tR values. Integration of the NAPS RI system into routine LC-MS anal. will improve compound identifications and help facilitate ease of data sharing.

Journal of Chromatography A published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C5H5NO3S, Category: pyridine-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Gyton, Matthew R. published the artcileA convenient method for the generation of {Rh(PNP)}⁺ and {Rh(PONOP)}⁺ fragments: reversible formation of vinylidene derivatives, Recommanded Product: 2,6-Bis((di-tert-butylphosphino)methyl)pyridine, the publication is Dalton Transactions (2019), 48(9), 2877-2880, database is CAplus and MEDLINE.

The substitution reactions of [Rh(COD)₂][BAr^F₄] with PNP and PONOP pincer ligands 2,6-bis(di-tert-butylphosphinomethyl)pyridine and 2,6-bis(di-tert-butylphosphinito)pyridine in the weakly coordinating solvent 1,2-F₂C₆H₄ are an operationally simple method for the generation of reactive formally 14 VE rhodium(I) adducts in solution Application of this methodol. enables synthesis of known adducts of CO, N₂, H₂, previously unknown water complexes, and novel vinylidene derivatives [Rh(pincer)(CCHR)][BAr^F₄] (R = tBu, 3,5-tBu₂C₆H₃), through reversible reactions with terminal alkynes.

Dalton Transactions published new progress about 338800-13-8. 338800-13-8 belongs to pyridine-derivatives, auxiliary class Bis-phosphine Ligands, name is 2,6-Bis((di-tert-butylphosphino)methyl)pyridine, and the molecular formula is C23H43NP2, Recommanded Product: 2,6-Bis((di-tert-butylphosphino)methyl)pyridine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Yamada, Masanori published the artcileProton conductivity of zwitterionic-type molecular solids under intermediate temperature and anhydrous conditions, HPLC of Formula: 636-73-7, the publication is Chemical Physics Letters (2005), 402(4-6), 324-328, database is CAplus.

Anhydrous proton conducting material for polymer electrolyte membrane fuel cell (PEFC) was prepared by the mixing of zwitterionic-type mol. solid 3-pyridinesulfonic acid (PS) and organic acid methylenediphosphonic acid (MP). As a result, PS mol., which has a sulfonic acid and a pyridine group in its structure, showed the proton conductivity of 4 × 10^-5 S cm^-1 at 160°C under anhydrous condition. Surprisingly, by the mixing of MP to PS material, the PS-MP composite material exhibited a conductivity of 2 × 10^-3 S cm^-1. Also, the conductivity of PS-MP composite material did not decrease under the heating at 160° for 50 h.

Chemical Physics Letters published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C11H14O4, HPLC of Formula: 636-73-7.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem