Month: December 2022

Galenko, E. E. published the artcileSynthesis of Water-Soluble α-Aminopyrroles, 1-(2-Amino-1H-pyrrol-3-yl)pyridinium Chlorides, Safety of 1-(Cyanomethyl)pyridin-1-ium chloride, the publication is Russian Journal of General Chemistry (2021), 91(7), 1424-1428, database is CAplus.

A method for the synthesis of water-soluble α-aminopyrroles, 1-(2-amino-1H-pyrrol-3-yl)pyridinium chlorides, by the reaction 1-(cyanomethyl)pyridinium chloride with alkyl 3-aryl-2H-azirine-2-carboxylates was developed.

Russian Journal of General Chemistry published new progress about 17281-59-3. 17281-59-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitrile,Salt, name is 1-(Cyanomethyl)pyridin-1-ium chloride, and the molecular formula is C7H7ClN2, Safety of 1-(Cyanomethyl)pyridin-1-ium chloride.

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

Gupta, Ankur published the artcileSynthesis of biologically potent novel 5-(2-bromopyridin-3-yl-amino)-2-alkyl/aryl-isoindoline-1,3-dione analogs via Buchwald-Hartwig C-N coupling reaction, COA of Formula: C5H5BrN2, the publication is Letters in Organic Chemistry (2013), 10(2), 139-146, database is CAplus.

A novel series of N-alkyl/aryl substituted phthalimide analogs containing 2-bromopyridyl functionality were synthesized applying optimized Buchwald-Hartwig amination conditions using palladium acetate, cesium carbonate, and ±BINAP in toluene at 110°C under argon atm. The target heteroaryl phthalimide derivatives were obtained in moderate yield ranging from 40% to 51%. In the extra precision (XP) docking studies, at the ATP site of human topoisomerase IIα (hTopoIIα) (PDB id 1ZXM), we identified that compound I (R = Me) demonstrated remarkable H-bond interactions with catalytic MG²⁺, ASN 91, SER 148, SER 149, ALA 167 and compound I (R = 3-pyridyl) with ARG 162, ASN 163, GLY 164, LSY 168, ASN 95 indicating their significance as a plausible hTopoIIα inhibitors. In the in vitro evaluation of A549 cell line, compounds I (R = Me, 3-pyridyl) were observed to have only moderate cytotoxicity (IC₅₀ 180μg/mL and 210μg/mL resp.). The developed process could be widely employed for the synthesis of novel heterocyclic compounds with one of the components as N-alkyl/aryl substituted phthalimide derivatives and has the potential to be developed as a major route for the identification of active drug candidates.

Letters in Organic Chemistry 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, COA of Formula: C5H5BrN2.

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

Shahar, Or David published the artcileA high-throughput chemical screen with FDA approved drugs reveals that the antihypertensive drug Spironolactone impairs cancer cell survival by inhibiting homology directed repair, Application In Synthesis of 54856-23-4, the publication is Nucleic Acids Research (2014), 42(9), 5689-5701, database is CAplus and MEDLINE.

DNA double-strand breaks (DSBs) are the most severe type of DNA damage. DSBs are repaired by non-homologous end-joining or homol. directed repair (HDR). Identifying novel small mols. that affect HDR is of great importance both for research use and therapy. Mols. that elevate HDR may improve gene targeting, whereas inhibiting mols. can be used for chemotherapy, since some of the cancers are more sensitive to repair impairment. Here, the authors performed a high-throughput chem. screen for FDA approved drugs, which affect HDR in cancer cells. The authors found that HDR frequencies are increased by retinoic acid and Idoxuridine and reduced by the antihypertensive drug Spironolactone. The authors further revealed that Spironolactone impairs Rad51 foci formation, sensitizes cancer cells to DNA damaging agents, to Poly (ADP-ribose) polymerase (PARP) inhibitors and crosslinking agents and inhibits tumor growth in xenografts, in mice. This study suggests Spironolactone as a new candidate for chemotherapy.

Nucleic Acids Research published new progress about 54856-23-4. 54856-23-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Salt,Amine,Inhibitor,Inhibitor, name is N-Methyl-2-(pyridin-2-yl)ethan-1-amine dimethanesulfonate, and the molecular formula is C18H12ClNO, Application In Synthesis of 54856-23-4.

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

Baydas, Yasemin published the artcileAsymmetric reduction of aromatic heterocyclic ketones with bio-based catalyst Lactobacillus kefiri P2, Related Products of pyridine-derivatives, the publication is Chemical Papers (2021), 75(3), 1147-1155, database is CAplus.

In this study, Lactobacillus kefiri P2 biocatalysts isolated from traditional dairy products, were used to catalyze the asym. reduction of prochiral ketones RC(O)R¹ (R = pyridin-2-yl, 2H-1,3-benzodioxol-5-yl, furan-2-yl, etc.; R¹ = Me, Ph, pyridin-2-yl) to chiral secondary alcs R/S-RCH(R¹)OH. Secondary chiral carbinols were obtained by asym. bioreduction of different prochiral substrates with results up to > 99% enantiomeric excess (ee). The compound R/S-RCH(R¹)OH (R = pyridin-2-yl, R¹ = Me (I)) which can be used in the synthesis of pharmaceuticals such as bufuralols potent nonselective β-blockers antagonists, Amiodarone (cardiac anti-arrhythmic), and Benziodarone (coronary vasodilator), was produced in gram-scale, high yield and enantiomerically pure form using L. kefiri P2 biocatalysts. The gram-scale production was carried out, and 9.70 g of I in enantiomerically pure form was obtained in 96% yield. Also, production of I in terms of yield and gram scale through catalytic asym. reduction using the biocatalyst was the highest report so far. This is a cost-effective, clean and eco-friendly process for the preparation of chiral secondary alcs. compared to chem. processes. From an environmental and economic perspective, this biocatalytic method has great application potential, making it a green and sustainable way of synthesis.

Chemical Papers 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, Related Products of pyridine-derivatives.

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

Malinowski, Marek published the artcileTitanium(0) reagents. III. A convenient preparation of 4-pyridinamine derivatives, HPLC of Formula: 18437-58-6, the publication is Journal fuer Praktische Chemie (Leipzig) (1988), 330(1), 154-8, database is CAplus.

Ti(0) slurry, easily accessible by the reduction of TiCl₄ with LiAlH₄ or Mg in THF, is an excellent reagent for the reduction of N-nitropyridine N-oxides, e.g., I (R = H, Me, F, Cl) to 4-aminopyridines, e.g., II. The reaction proceeds smoothly and fast at room temperature giving the amines in >90% yields.

Journal fuer Praktische Chemie (Leipzig) 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, HPLC of Formula: 18437-58-6.

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

Krah, Sabrina published the artcileElectron-Rich Silicon Containing Phosphinanes for Rapid Pd-Catalyzed C-X Coupling Reactions, Formula: C5H6BNO2, the publication is ChemCatChem (2022), 14(16), e202200734, database is CAplus.

Novel silicon-containing phosphine, 4,1-phosphasilinane 2-TripC₆H₄P(CH₂CH₂)₂SiMe₂ (SabPhos, Trip = 2,4,6-ⁱPr₃C₆H₂) was prepared as a ligand for palladium-catalyzed coupling reactions. Palladium-catalyzed cross-coupling reactions are among the most useful and efficient methods for direct access to complex structures in organic synthesis. However, heteroatom-containing compounds can complicate such coupling reactions due to their competitive coordination with the palladium catalyst and electronic effects. As a result, good yields are often only obtained under harsher reaction conditions, such as high temperatures and long reaction times. Here the design of a highly active phosphine ligand is reported that provides excellent yields for C-N coupling reactions at ambient temperature Incorporation of the phosphorus atom into a cyclohexane ring maintains the pyramidal structure of the phosphorus while reducing steric hindrance. This, and a silicon atom in the cyclohexane moiety, results in an electron-rich phosphinane ligand. This novel silicon containing SabPhos ligand can be obtained in excellent yields in a straightforward synthesis. In palladium catalyzed reactions, this ligand facilitates the coupling of a broad range of heteroaryl chlorides via C-C bonds with boronic acids and C-N bonds with secondary amines in excellent yields under mild conditions.

ChemCatChem 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

Lee, Dong-Hwan published the artcileHighly active and recyclable silica gel-supported palladium catalyst for mild cross-coupling reactions of unactivated heteroaryl chlorides, Recommanded Product: 2-Pyridinylboronic acid, the publication is Green Chemistry (2010), 12(11), 2024-2029, database is CAplus.

Silica gel-supported β-ketoiminatophosphane-Pd complex (Pd@O₂) was shown to be a highly active and long-lived catalyst for aqueous Suzuki, Stille and Sonogashira coupling reactions of heteroaryl chlorides. A wide range of heteroaryl chlorides could be efficiently coupled with different nucleophilic partners in the presence of only 0.5 mol% catalyst and under mild conditions. This is one of the most powerful heterogeneous catalysts for the couplings of diverse heteroaryl chlorides. Furthermore, the catalyst could be reused with almost consistent activity.

Green 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, Recommanded Product: 2-Pyridinylboronic acid.

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

Moree, Wilna J. published the artcileNovel benzothiophene H₁-antihistamines for the treatment of insomnia, Name: 4-Fluoropicolinonitrile, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(7), 2316-2320, database is CAplus and MEDLINE.

SAR of lead benzothiophene H₁-antihistamine I (R = 2-pyridyl) was explored to identify backup candidates with suitable pharmacokinetic profiles for an insomnia program. Several potent and selective H₁-antihistamines with a range of projected half-lives in humans were identified. Had a suitable human half-life as demonstrated in a human microdose study, but variability in pharmacokinetic profile, attributed to metabolic clearance, prevented further development of this compound I (R = 1-pyrazolyl) demonstrated lower predicted clearance in preclin. studies, and may represent a more suitable backup compound

Bioorganic & Medicinal Chemistry Letters published new progress about 847225-56-3. 847225-56-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Fluoride,Nitrile, name is 4-Fluoropicolinonitrile, and the molecular formula is C6H3FN2, Name: 4-Fluoropicolinonitrile.

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

Guo, Peng-Fei published the artcileC-H Arylation of Pyridines: High Regioselectivity as a Consequence of the Electronic Character of C-H Bonds and Heteroarene Ring, HPLC of Formula: 89076-64-2, the publication is Journal of the American Chemical Society (2011), 133(41), 16338-16341, database is CAplus and MEDLINE.

A new catalytic protocol for highly selective C-H arylation of pyridines containing common and synthetically versatile electron-withdrawing substituents (NO₂, CN, F and Cl) is reported. The new protocol expands the scope of catalytic azine functionalization as the excellent regioselectivity at the 3- and 4-positions well complements the existing methods for C-H arylation and Ir-catalyzed borylation, as well as classical functionalization of pyridines. Another important feature of the new method is its flexibility to adapt to challenging substrates by a simple modification of the carboxylic acid ligand or the use of silver salts. The regioselectivity can be rationalized on the basis of the key electronic effects (repulsion between the nitrogen lone pair and polarized C-Pd bond at C2-/C6-positions and acidity of the C-H bond) in combination with steric effects (sensitivity to bulky substituents).

Journal of the American Chemical Society published new progress about 89076-64-2. 89076-64-2 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitro Compound,Benzene, name is 5-Nitro-2-phenylpyridine, and the molecular formula is C11H8N2O2, HPLC of Formula: 89076-64-2.

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

Hansen, Marvin M. published the artcileBoronic Acids and Derivatives-Probing the Structure-Activity Relationships for Mutagenicity, Computed Properties of 197958-29-5, the publication is Organic Process Research & Development (2015), 19(11), 1507-1516, database is CAplus.

Despite a recent publication describing boronic acids as a “novel class of bacterial mutagen,” process and anal. chemists may not be aware of the potential worker exposure hazards, or of the need to assess boron compounds as potential genotoxic impurities (GTIs) per ICH M7. This publication provides new Ames data for 44 com. available boronic acids, boronic acid derivatives, and boron-containing reagents. Trends in the Ames data are discussed from a structure-activity perspective. Common reagents such as bis(pinacolato)diboron and bis-boronic acid were shown to be mutagenic in the Ames assay. Currently available in silico computational models were found to provide little value in predicting the outcome of the Ames assay for boronic acids and derivatives The authors propose oxygen-mediated oxidation of boron compounds to generate organic radicals as a potential mechanism for mutagenicity. It is hoped that this paper will result in increased awareness of this class of GTIs and prompt publication of addnl. Ames data for boronic acids and their derivatives that will lead to improved (Q)SAR models and an understanding of the mechanism of mutagenicity.

Organic Process Research & Development 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