Day: December 8, 2022

Musci, Pantaleo published the artcileFlow technol. for telescoped generation, lithiation and electrophilic (C₃) functionalization of highly strained 1-azabicyclo[1.1.0]butanes, SDS of cas: 91-02-1, the publication is Angewandte Chemie, International Edition (2021), 60(12), 6395-6399, database is CAplus and MEDLINE.

Strained compounds are privileged moieties in modern synthesis. In this context, 1-azabicyclo[1.1.0]butanes are appealing structural motifs that can be employed as click reagents or precursors to azetidines. We herein report the first telescoped continuous flow protocol for the generation, lithiation, and electrophilic trapping of 1-azabicyclo[1.1.0]butanes. The flow method allows for exquisite control of the reaction parameters, and the process operates at higher temperatures and safer conditions with respect to batch mode. The efficiency of this intramol. cyclization/C3-lithiation/electrophilic quenching flow sequence is documented with more than 20 examples.

Angewandte Chemie, International Edition 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, SDS of cas: 91-02-1.

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

Nerush, Alexander published the artcileTemplate Catalysis by Metal-Ligand Cooperation. C-C Bond Formation via Conjugate Addition of Non-activated Nitriles under Mild, Base-free Conditions Catalyzed by a Manganese Pincer Complex, Category: pyridine-derivatives, the publication is Journal of the American Chemical Society (2016), 138(22), 6985-6997, database is CAplus and MEDLINE.

The first example of a catalytic Michael addition reaction of non-activated aliphatic nitriles to α,β-unsaturated carbonyl compounds under mild, neutral conditions is reported. A new de-aromatized pyridine-based PNP pincer complex of the Earth-abundant, first-row transition metal manganese serves as the catalyst. The reaction tolerates a variety of nitriles and Michael acceptors with different steric features and acceptor strengths. Mechanistic investigations including temperature-dependent NMR spectroscopy and DFT calculations reveal that the cooperative activation of alkyl nitriles, which leads to the generation of metalated nitrile nucleophile species (α-cyano carbanion analogs), is a key step of the mechanism. The metal center is not directly involved in the catalytic bond formation but rather serves, cooperatively with the ligand, as a template for the substrate activation. This approach of “template catalysis” expands the scope of potential donors for conjugate addition reactions.

Journal of the American Chemical Society 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, Category: pyridine-derivatives.

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

Bumagin, N. A. published the artcileAn effective activation of palladium phosphine complexes in aqueous phase reactions of heteroaromatic boronic acids with aryl halides, Formula: C5H5BrN2, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2014), 50(1), 19-25, database is CAplus.

A simple and effective method was developed for the activation of palladium-phosphine complexes in the Suzuki reaction (TON up to 9800, TOF up to 58800 h^-1) by selecting an aqueous reaction medium instead of organic solvents. This method was elaborated for a high yield synthesis of heteroaromatic biaryls with furyl and thienyl groups.

Chemistry of Heterocyclic Compounds (New York, NY, United States) 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, Formula: C5H5BrN2.

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

Elie, Jonathan published the artcileDesign of selective COX-2 inhibitors in the (aza)indazole series. Chemistry, in vitro studies, radiochemistry and evaluations in rats of a [¹⁸F] PET tracer, Quality Control of 612845-44-0, the publication is Journal of Enzyme Inhibition and Medicinal Chemistry (2019), 34(1), 1-7, database is CAplus and MEDLINE.

A series of novel derivatives exhibiting high affinity and selectivity towards the COX-2 enzyme in the (aza) indazole series was developed. A short synthetic route involving a bromination/arylation sequence under microwave irradiation and direct C-H activation were established in the indazole and azaindazole series resp. In vitro assays were conducted and structural modifications were carried out on these scaffolds to furnish compound which exhibited effective COX-2 inhibitory activity, with IC₅₀ values of 0.409 μM and an excellent selectivity vs. COX-1. Radiolabeling of this most potent derivative [¹⁸F] was achieved after boron ester release and the tracer was evaluated in vivo in a rat model of neuroinflammation. All chem., radiochem. and biol. exptl. data are discussed.

Journal of Enzyme Inhibition and 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, Quality Control of 612845-44-0.

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

Kandasamy, M. published the artcileMolecular structure and vibrational spectra of 3-and 4-amino-2-bromopyridine by density functional methods, Safety of 2-Bromopyridin-3-amine, the publication is Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy (2012), 206-216, database is CAplus and MEDLINE.

Exptl. and theor. study on the mol. structure and the vibrational spectra of 3-amino-2-bromopyridine (Compound I) and 4-amino-2-bromopyridine (Compound II) are presented. The vibrational frequencies of these compounds were obtained theor. by DFT/B3LYP employing the 6-311G(2df,2p) basis set for optimized geometries and were compared with FTIR solid phase spectra (FTIR) at 400-4000 cm^-1, FT-Raman spectra at 100-4000 cm^-1 and with solution phase spectra at 400-4000 cm^-1. Complete vibrational assignment, anal. and correlation of the fundamental modes for these compounds were carried based on the potential energy distribution (PED). The vibrational harmonic frequencies were scaled using scale factors, yielding a good agreement between the exptl. recorded and the theor. calculated values. Finally the calculated HOMO and LUMO energies are localized on the entire ring and substituents.

Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 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, Safety of 2-Bromopyridin-3-amine.

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

Mikhailov, B. M. published the artcileOrganoboron compounds. Synthesis of complex compounds of unsymmetric borontriaryls, COA of Formula: C23H20BN, the publication is Doklady Akademii Nauk SSSR (1956), 94-7, database is CAplus.

All operations with Li derivatives described below were performed under N. To 0.07 mol 1-C₁₀H₇Li in Et₂O was added at -10° in 1 h. 16.6 g. Ph₂BOCH₂CHMe₂; after 2 h. at room temperature there was obtained a precipitate of 30% [Ph₂(1-C₁₀H₇)BOCH₂CHMe₂]Li.2Et₂O (I), a crystalline solid. The filtrate from this was treated with NH₃ yielding 30% 1-C₁₀H₇BPh₂.NH₃, a solid (from C₆H₆-pentane). Similarly, 0.028 mol PhLi and 9.4 g. iso-BuOB(C₁₀H₇-1)₂ gave 80% [(1-C₁₀H₇)₂BPhOCH₂CHMe₂]Li (II). I (0.9 g.) in Et₂O-C₆H₆ was treated with 0.5 mL. pyridine; after evaporation the residue was treated with H₂O yielding an insoluble precipitate of 88% [Ph₂B(1-C₁₀H₇)].C₅H₅N, m. 170-5°. Similarly, II gave 80% (1-C₁₀H₇)₂BPh.C₅H₅N, m. 213-15°. Similarly was prepared 46% (1-C₁₀H₇)₂(o-MeC₆H₄)B.C₅H₅N, m. 203-5°. Passage of NH₃ into II in Et₂O gave after evaporation of solvent and dilution with H₂O 75% insoluble (1-C₁₀H₇)₂BPh.NH₃, m. 170-3° (shrinks at 135-44°). From o-MeC₆H₄Li and iso-BuOBPh₂ was prepared the complex Li salt (IIa) which treated with NH₃ in Et₂O gave 54.5% (o-MeC₆H₄)BPh₂.NH₃, m. 175-8° (shrinks at 147-50°), while the filtrate on addition of KBr gave o-MeC₆H₄BPh₂K, colorless crystals. Similarly, PhLi and iso-BuOBPh₂ gave 65% Ph₃B.NH₃, m. 202-4°, while the filtrate with KBr gave a little Ph₄BK. Passage of dry HCl into I in C₆H₆, filtration and evaporation gave a residue which taken up in pentane and treated with NH₃ gave 97% Ph₂BOCH₂CHMe₂.NH₃ (III), m. 101-3°, while the filtrate gave C₁₀H₈; III, m. 103-5°, forms from NH₃ and the ester directly. Similarly IIa treated with HCl, then with NH₃ as above gave 70% III. Treatment of III with 1 mol PhLi in Et₂O gave 50% Ph₃B.NH₃. Addition of 0.0043 mol iso-BuOBPh₂ to 0.005 mol PhLi without cooling in Et₂O followed by 1 mol pyridine rapidly gave 96% Ph₃B.C₅H₅N, decompose 215°. Similarly were prepared o-MeC₆H₄BPh₂.C₅H₅N, m. 172-4°, and 85% (1-C₁₀H₇)₂(o-MeC₆H₄)B.C₅H₅N, m. 203-5°.

Doklady Akademii Nauk SSSR published new progress about 971-66-4. 971-66-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is Triphenyl(pyridin-1-ium-1-yl)borate, and the molecular formula is C23H20BN, COA of Formula: C23H20BN.

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

Darden, Carly M. published the artcileCalcineurin/NFATc2 and PI3K/AKT signaling maintains β-cell identity and function during metabolic and inflammatory stress, Category: pyridine-derivatives, the publication is iScience (2022), 25(4), 104125, database is CAplus and MEDLINE.

Pancreatic islets respond to metabolic and inflammatory stress by producing hormones and other factors that induce adaptive cellular and systemic responses. Here we show that intracellular Ca2+ ([Ca2+]i) and ROS signals generated by high glucose and cytokine-induced ER stress activate calcineurin (CN)/NFATc2 and PI3K/AKT to maintain β-cell identity and function. This was attributed in part by direct induction of the endocrine differentiation gene RFX6 and suppression of several β-cell “disallowed” genes, including MCT1. CN/NFATc2 targeted p300 and HDAC1 to RFX6 and MCT1 promoters to induce and suppress gene transcription, resp. In contrast, prolonged exposure to stress, hyperstimulated [Ca2+]i, or perturbation of CN/NFATc2 resulted in downregulation of RFX6 and induction of MCT1. These findings reveal that CN/NFATc2 and PI3K/AKT maintain β-cell function during acute stress, but β-cells dedifferentiate to a dysfunctional state upon loss or exhaustion of Ca2+/CN/NFATc2 signaling. They further demonstrate the utility of targeting CN/NFATc2 to restore β-cell function.

iScience published new progress about 21829-25-4. 21829-25-4 belongs to pyridine-derivatives, auxiliary class Membrane Transporter/Ion Channel,Calcium Channel, name is Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, and the molecular formula is C17H18N2O6, Category: pyridine-derivatives.

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

Panicker, C. Yohannan published the artcileFT-IR, FT-Raman and SERS spectra of pyridine-3-sulfonic acid, Application In Synthesis of 636-73-7, the publication is Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy (2006), 64A(3), 744-747, database is CAplus and MEDLINE.

FTIR and FT-Raman spectra of pyridine-3-sulfonic acid are recorded and analyzed. Surface enhanced Raman scattering (SERS) spectrum is recorded in a Ag colloid. The bands due to υCH, υSO are enhanced in the SERS spectrum. A likely perpendicular orientation’ of the mol. on the Ag surface is suggested.

Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 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 In Synthesis of 636-73-7.

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