Tag: M.W=150-200

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

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

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

Chen, Li published the artcileAmide derivatives of Gallic acid: Design, synthesis and evaluation of inhibitory activities against in vitro α-synuclein aggregation, Application of Pyridine-3-sulfonic acid, the publication is Bioorganic & Medicinal Chemistry (2020), 28(15), 115596, database is CAplus and MEDLINE.

Gallic acid (GA), a natural phenolic acid, has received numerous attention because of its anti-oxidative, anti-inflammatory, and anti-cancer activity. More importantly, GA can act as an efficient inhibitor of α-Synuclein (α-Syn) aggregation at early stages. Nevertheless, some evidences suggest that GA is unlikely to cross the blood-brain barrier because of its high hydrophilicity. Hence, GA may not be considered as a promising candidate or entering brain and directly affecting the central nervous system. Accordingly, we have designed and synthesized a series of amide derivatives of GA, some of which possess appropriate lipophilicity and hydrophilicity with LogP (2.09-2.79). Meanwhile, these sheet-like conjugated compounds have good π-electron delocalization and high ability of hydrogen-bond formation. Some compounds have shown better in vitro anti-aggregation activities than GA towards α-Syn, with IC₅₀ down to 0.98μM. The valid modification strategy of GA is considered an efficient way to discover novel inhibitors of α-Syn aggregation.

Bioorganic & Medicinal Chemistry 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, Application of Pyridine-3-sulfonic acid.

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

Li, Jian-Yuan published the artcileDevelopment of DNA-Compatible Suzuki-Miyaura Reaction in Aqueous Media, Computed Properties of 1008506-24-8, the publication is Bioconjugate Chemistry (2018), 29(11), 3841-3846, database is CAplus and MEDLINE.

DNA-encoded chem. libraries (DELs) are a cost-effective technol. for the discovery of novel chem. probes and drug candidates. A major limiting factor in assembling productive DELs is the availability of DNA-compatible chem. reactions in aqueous media. In an effort to increase the chem. accessibility and structural diversity of small mols. displayed by DELs, the authors developed a robust Suzuki-Miyaura reaction protocol that is compatible with the DNA structures. By employing a water-soluble Pd-precatalyst, the authors developed conditions that allow efficient coupling of DNA-linked aryl halides with a wide variety of boronic acids/esters including heteroaryl boronates.

Bioconjugate Chemistry published new progress about 1008506-24-8. 1008506-24-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Ether,Pyridine,Boronic Acids,Boronic acid and ester, name is 3-Methoxypyridine-4-boronic acid, and the molecular formula is C6H8BNO3, Computed Properties of 1008506-24-8.

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

Zhang, Han published the artcileDesign, synthesis and biological activities of piperidine-spirooxadiazole derivatives as α7 nicotinic receptor antagonists, Product Details of C6H8BNO3, the publication is European Journal of Medicinal Chemistry (2020), 112774, database is CAplus and MEDLINE.

7 Nicotinic acetylcholine receptors (nAChRs) expressed in the nervous and immune systems was suggested to play important roles in the control of inflammation. However, the lack of antagonist tools specifically inhibiting α7 nAChR impedes the validation of the channel as therapeutic target. To discover a selective α7 antagonist, a pharmacophore-based virtual screening and identified a piperidine-spirooxadiazole derivative T761-0184 that acts as a α7 antagonist. A series of novel piperidine-spirooxadiazole derivatives were subsequently synthesized and evaluated using two-electrode voltage clamp (TEVC) assay in Xenopus oocytes. Lead compounds from two series inhibited α7 with their IC₅₀ values ranging from 3.3μM to 13.7μM. Compound 3-(4-Bromophenyl)-8-methyl-1-oxa-2,4,8-triazaspiro[4.5]dec-2-ene exhibited α7 selectivity over other α4β2 and α3β4 nAChR subtypes. The anal. of structure-activity relationship (SAR) provides valuable insights for further development of selective α7 nAChR antagonists.

European Journal of Medicinal Chemistry published new progress about 1008506-24-8. 1008506-24-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Ether,Pyridine,Boronic Acids,Boronic acid and ester, name is 3-Methoxypyridine-4-boronic acid, and the molecular formula is C13H10F2, Product Details of C6H8BNO3.

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

Murayama, Hiroaki published the artcileIridium-Catalyzed Enantioselective Transfer Hydrogenation of Ketones Controlled by Alcohol Hydrogen-Bonding and sp³-C-H Noncovalent Interactions, Application of Phenyl(pyridin-2-yl)methanone, the publication is Advanced Synthesis & Catalysis (2020), 362(21), 4655-4661, database is CAplus.

Iridium-catalyzed enantioselective transfer hydrogenation of ketones with formic acid was developed using a prolinol-phosphine chiral ligand. Cooperative action of the iridium atom and the ligand through alc.-alkoxide interconversion was crucial to facilitate the transfer hydrogenation. Various ketones including alkyl aryl ketones, ketoesters, and an aryl heteroaryl ketone were competent substrates. An attractive feature of this catalysis was efficient discrimination between the alkyl and aryl substituents of the ketones, promoting hydrogenation with the identical sense of enantioselection regardless of steric demand of the alkyl substituent and thus resulting in a rare case of highly enantioselective transfer hydrogenation of tert-alkyl aryl ketones. Quantum chem. calculations revealed that the sp³-C-H/π interaction between an sp³-C-H bond of the prolinol-phosphine ligand and the aryl substituent of the ketone was crucial for the enantioselection in combination with O-H···O/sp³-C-H···O two-point hydrogen-bonding between the chiral ligand and carbonyl group.

Advanced Synthesis & 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 C12H9NO, Application of Phenyl(pyridin-2-yl)methanone.

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

Maust, Mark C. published the artcileSwitchable Regioselective 6-endo or 5-exo Radical Cyclization via Photoredox Catalysis, SDS of cas: 39856-58-1, the publication is Journal of the American Chemical Society (2022), 144(9), 3776-3781, database is CAplus and MEDLINE.

Here a simple method for reagent controlled regioselective radical cyclization of halogenated N-heterocycles onto pendant olefins was developed. Radical generation occurs under mild photoredox conditions with control of the regioselectivity governed by the rate of hydrogen atom transfer (HAT). Utilizing a polarity-matched thiol-based HAT agent promoted the highly selective formation of the 5-exo cyclization product. Conversely, limiting the solubility of the HAT reagent Hantzsch ester (HEH) leads to selective formation of the thermodynamically favored 6-endo product. This occurs through an initial 5-exo cyclization, with the resulting alkyl radical intermediate undergoing neophyl rearrangement to form the 6-endo product. Development of this switchable catalysis strategy allows for two modes of divergent reactivity to form either the 6-endo or 5-exo product, generating fused N-heteroaromatic/saturated ring systems.

Journal of the American Chemical Society published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, SDS of cas: 39856-58-1.

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

Fontaine, Fanny published the artcileFirst identification of boronic species as novel potential inhibitors of the Staphylococcus aureus NorA efflux pump, Recommanded Product: (6-Ethoxypyridin-3-yl)boronic acid, the publication is Journal of Medicinal Chemistry (2014), 57(6), 2536-2548, database is CAplus and MEDLINE.

Overexpression of efflux pumps is an important mechanism of bacterial resistance that results in the extrusion of antimicrobial agents outside the bacterial cell. Inhibition of such pumps appears to be a promising strategy that could restore the potency of existing antibiotics. The NorA efflux pump of Staphylococcus aureus confers resistance to a wide range of unrelated substrates, such as hydrophilic fluoroquinolones, leading to a multidrug-resistance phenotype. Here, 150 heterocyclic boronic species were evaluated for their activity against susceptible and resistant strains of S. aureus. Twenty-four hit compounds, although inactive when tested alone, were found to potentiate ciprofloxacin activity by a 4-fold increase at concentrations ranging from 0.5 to 8 μg/mL against S. aureus 1199B, which overexpresses NorA. Boron-free analogs showed no biol. activity, thus revealing that the boron atom is crucial for biol. activity. This work describes the first reported efflux pump inhibitory activity of boronic acid derivatives

Journal of Medicinal Chemistry published new progress about 612845-44-0. 612845-44-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Ether,Boronic Acids,Boronic acid and ester, name is (6-Ethoxypyridin-3-yl)boronic acid, and the molecular formula is C7H10BNO3, Recommanded Product: (6-Ethoxypyridin-3-yl)boronic acid.

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

Kondoh, Azusa published the artcileFormal umpolung addition of phosphites to 2-azaaryl Ketones under chiral Broensted base catalysis: enantioselective protonation utilizing [1,2]-phospha-Brook rearrangement, HPLC of Formula: 91-02-1, the publication is Chemistry – A European Journal (2022), 28(42), e202201240, database is CAplus and MEDLINE.

The formal enantioselective umpolung addition of dialkyl phosphites to 2-azaaryl ketones was developed under Broensted base catalysis. The reaction involved the enantioselective protonation of the transient α-oxygenated (2-azaaryl)methyl anion generated through the 1,2-addition of the anion of dialkyl phosphite to the 2-azaaryl ketone and the subsequent [1,2]-phospha-Brook rearrangement. A chiral bis(guanidino)iminophosphorane organosuperbase efficiently catalyzed the reaction to provide enantio-enriched phosphates in high yields with good to high enantioselectivities. This is a rare example of the catalytic enantioselective protonation of transient carbanions other than enolates, constructing a trisubstituted stereogenic center α to 2-azaarenes.

Chemistry – A European Journal 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 C12H9NO, HPLC of Formula: 91-02-1.

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