Tag: M.W=100-150

Li, Yabo published the artcileDirect C-H Arylation of Thiophenes at Low Catalyst Loading of a Phosphine-Free Bis(alkoxo)palladium Complex, Formula: C5H6BNO2, the publication is Journal of Organic Chemistry (2014), 79(7), 2890-2897, database is CAplus and MEDLINE.

An efficient phosphine-free direct C-H arylation of thiophenes at the α-position has been developed at low catalyst loading of bis(alkoxo)palladium complex ( 0.1-0.2 mol %). The developed synthetic method can be applied to the synthesis of α-aryl/heteroaryl thiophenes from aryl or heteroaryl bromides in good to excellent yields and is compatible with the substrates bearing electron-donating or electron-withdrawing groups. The reactivities of the 2- and 5-positions of thiophenes are equivalent and not dependent on steric hindrance under optimal conditions. This condition can also be applied to other heterocyclic moieties such as benzothiophene, benzofuran, and pyrrole with high conversion yields.

Journal of Organic 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, Formula: C5H6BNO2.

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

Yang, Xiaoyu published the artcileRedox-triggered switchable synthesis of 3,4-dihydroquinolin-2(1H)-one derivatives via hydride transfer/N-dealkylation/N-acylation, Computed Properties of 197958-29-5, the publication is Organic Letters (2021), 23(2), 358-364, database is CAplus and MEDLINE.

The switchable synthesis of 3-non, 3-mono, 3,3′-disubstituted 3,4-dihydroquinolin-2(1H)-ones was developed through a redox-neutral hydride-transfer/N-dealkylation/N-acylation strategy from o-aminobenzaldehyde with 4-hydroxycoumarin, and Meldrum’s acid, resp. The unprecedented strategy for the synthesis of 3,3′-highly functionalized 3,4-dihydroquinolin-2(1H)-one has been realized with the in situ utilization of the released HCHO via the o-QM involved Michael addition In addition, the synthetic utility of this protocol has been well illustrated via concise synthesis of CYP11B2 inhibitor.

Organic Letters 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 C5H11NO2S, Computed Properties of 197958-29-5.

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

Dehnhardt, Christoph M. published the artcileLead Optimization of N-3-Substituted 7-Morpholinotriazolopyrimidines as Dual Phosphoinositide 3-Kinase/Mammalian Target of Rapamycin Inhibitors: Discovery of PKI-402, Recommanded Product: 4-Amino-2-picoline, the publication is Journal of Medicinal Chemistry (2010), 53(2), 798-810, database is CAplus and MEDLINE.

Herein we describe the identification and lead optimization of triazolopyrimidines as a novel class of potent dual PI3K/mTOR inhibitors, resulting in the discovery of 3 (PKI-402, I). Compound 3 exhibits good phys. properties and PK parameters, low nanomolar potency against PI3Kα and mTOR, and excellent inhibition of cell proliferation in several human cancer cell lines. Furthermore, in vitro and in vivo biomarker studies demonstrated the ability of 3 to shut down the PI3K/Akt pathway and induce apoptosis in cancer cells. In addition, 3 showed excellent in vivo efficacy in various human cancer xenografts, validating suppression of PI3K/mTOR signaling as a potential anticancer therapy.

Journal of Medicinal Chemistry 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 C6H8N2, Recommanded Product: 4-Amino-2-picoline.

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

Milicevic Sephton, Selena published the artcileSynthesis and Biological Evaluation of Quinoxaline Derivatives for PET Imaging of the NMDA Receptor, Computed Properties of 197958-29-5, the publication is Helvetica Chimica Acta (2017), 100(12), n/a, database is CAplus.

Due to the biol. complexity of the N-methyl-D-aspartate receptor (NMDAR), the development of a positron emission tomog. radiotracer for the imaging of NMDAR has met with limited success. Recent studies have established the presence of GluN2A subunit of the NMDAR in the heart and its role in the regulation of intracellular calcium levels. In our efforts to develop an imaging agent for the GluN2A subunit, we designed three new compounds based on a quinoxaline scaffold. The synthesis of the analogs was based on a two-step Kabachnik-Fields reaction in sequence with Suzuki cross-coupling and acid hydrolysis. They exhibited comparable high binding affinity values below 5 nM. A two-step radiolabeling procedure was successfully developed for the synthesis of [¹⁸F]I. [¹⁸F]I was obtained in a modest overall radiochem. yield of 5.5 ± 4.2%, a good specific radioactivity of 254 ± 158 GBq/μmol, and a radiochem. purity > 99%. While two compounds showed comparable binding affinity towards NMDAR, sluggish radiolabeling, prevented their further evaluation. For [¹⁸F]I, in vitro autoradiog. on rat heart slices demonstrated heterogeneous but unspecific accumulation, whereas for the brain a high in vitro specificity towards NMDAR, could be demonstrated.

Helvetica Chimica Acta 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, Computed Properties of 197958-29-5.

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

Hansen, Helge-Boj published the artcileThe Stronger the Better: Donor Substituents Push Catalytic Activity of Molecular Chromium Olefin Polymerization Catalysts, Recommanded Product: 4-Amino-2-picoline, the publication is Chemistry – A European Journal (2021), 27(43), 11084-11093, database is CAplus and MEDLINE.

The donor strength of bifunctional pyridine-cyclopentadienyl ligands was altered systematically by the introduction of donating groups in the para-position of the pyridine. In the resulting chromium complexes an almost linear correlation between donor strength and the nitrogen-chromium distance as well as the electronic absorption maximum is exptl. observed The connection of electron-donating groups in the ligand backbone leads to an efficient transfer of the electronic influences to the catalytically active metal center without restricting it through steric effects. Therefore, catalytic olefin polymerization activity, which is already very high for the previously studied catalysts, increase considerably by attaching para-amino groups to the chelating pyridine or quinoline, resp. Combining electron-rich indenyl ligands with para-amino substituted pyridines lead to the highest catalytic activities observed so far for this class of organo chromium olefin polymerization catalysts. The resulting polymers are of ultra-high mol. weight and the ability of the catalysts to incorporate co-monomers is also very high.

Chemistry – A European Journal 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 C6H8N2, Recommanded Product: 4-Amino-2-picoline.

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

Owen, Dafydd R. published the artcileIdentification, synthesis and SAR of amino substituted pyrido[3,2b]pyrazinones as potent and selective PDE5 inhibitors, Application of (6-Hydroxypyridin-3-yl)boronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(15), 4088-4091, database is CAplus and MEDLINE.

A new class of potent and selective PDE5 inhibitors is disclosed. Guided by X-ray crystallog. data, optimization of an HTS lead led to the discovery of a series of 2-aryl-8-alkyl-6-aminopyrido[3,2b]pyrazinones which show potent inhibition of the PDE5 enzyme. Synthetic details and some structure-activity relationships are also presented.

Bioorganic & Medicinal Chemistry Letters 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, Application of (6-Hydroxypyridin-3-yl)boronic acid.

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

Hao, Cheng Yi published the artcileCarbonylative coupling of aryl tosylates/triflates with arylboronic acids under CO atmosphere, Synthetic Route of 197958-29-5, the publication is RSC Advances (2016), 6(89), 86502-86509, database is CAplus.

The carbonylative Suzuki-Miyaura reaction between aryl tosylates/triflates with arylboronic acid was reported, using base-free conditions and a balloon pressure of carbon monoxide. Under these conditions, unsym. biaryl ketones were obtained in modest to excellent yields. This method was adapted to the synthesis of oxybenzone and ketoprofen in good yields under mild conditions.

RSC Advances 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, Synthetic Route of 197958-29-5.

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

Degnan, Andrew P. published the artcileBiaryls as potent, tunable dual neurokinin 1 receptor antagonists and serotonin transporter inhibitors, Safety of 2-Pyridinylboronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2015), 25(15), 3039-3043, database is CAplus and MEDLINE.

Depression is a serious illness that affects millions of patients. Current treatments are associated with a number of undesirable side effects. Neurokinin 1 receptor (NK₁R) antagonists have recently been shown to potentiate the antidepressant effects of serotonin-selective reuptake inhibitors (SSRIs) in a number of animal models. Herein we describe the optimization of a biaryl chemotype to provide a series of potent dual NK₁R antagonists/serotonin transporter (SERT) inhibitors. Through the choice of appropriate substituents, the SERT/NK₁R ratio could be tuned to afford a range of target selectivity profiles. This effort culminated in the identification of an analog that demonstrated oral bioavailability, favorable brain uptake, and efficacy in the gerbil foot tap model. Ex vivo occupancy studies with compound 58 demonstrated the ability to maintain NK₁ receptor saturation (>88% occupancy) while titrating the desired level of SERT occupancy (11-84%) via dose selection.

Bioorganic & Medicinal Chemistry Letters 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, Safety of 2-Pyridinylboronic acid.

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

Wang, Tao published the artcileDiscovery of the Human Immunodeficiency Virus Type 1 (HIV-1) Attachment Inhibitor Temsavir and Its Phosphonooxymethyl Prodrug Fostemsavir, Synthetic Route of 197958-29-5, the publication is Journal of Medicinal Chemistry (2018), 61(14), 6308-6327, database is CAplus and MEDLINE.

The optimization of the 4-methoxy-6-azaindole series of HIV-1 attachment inhibitors (AIs) that originated with 1 to deliver temsavir (3, BMS-626529) is described. The most beneficial increases in potency and pharmacokinetic (PK) properties were attained by incorporating N-linked, sp²-hybridized heteroaryl rings at the 7-position of the heterocyclic nucleus. Compounds that adhered to a coplanarity model afforded targeted antiviral potency, leading to the identification of 3 with characteristics that provided for targeted exposure and PK properties in three preclin. species. However, the phys. properties of 3 limited plasma exposure at higher doses, both in preclin. studies and in clin. trials as the result of dissolution- and/or solubility-limited absorption, a deficiency addressed by the preparation of the phosphonooxymethyl prodrug 4 (BMS-663068, fostemsavir). An extended-release formulation of 4 is currently in phase III clin. trials where it has shown promise as part of a drug combination therapy in highly treatment-experienced HIV-1 infected patients.

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 C11H15NO2, Synthetic Route of 197958-29-5.

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

Zhuang, Linghang published the artcileDiscovery of BI 135585, an in vivo efficacious oxazinanone-based 11β hydroxysteroid dehydrogenase type 1 inhibitor, Formula: C5H6BNO2, the publication is Bioorganic & Medicinal Chemistry (2017), 25(14), 3649-3657, database is CAplus and MEDLINE.

A potent, in vivo efficacious 11β hydroxysteroid dehydrogenase type 1 (11β HSD1) inhibitor (I) has been identified. Compound I inhibited 11β HSD1 activity in human adipocytes with an IC₅₀ of 4.3 nM and in primary human adipose tissue with an IC₈₀ of 53 nM. Oral administration of I to cynomolgus monkey inhibited 11β HSD1 activity in adipose tissue. Compound I exhibited >1000× selectivity over other hydroxysteroid dehydrogenases, displays desirable pharmacodynamic properties and entered human clin. trials in 2011.

Bioorganic & 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 C12H16O3, Formula: C5H6BNO2.

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