Category: 18437-58-6

Aoki, Toshihiro published the artcileOptimizing the Physicochemical Properties of Raf/MEK Inhibitors by Nitrogen Scanning, Synthetic Route of 18437-58-6, the publication is ACS Medicinal Chemistry Letters (2014), 5(4), 309-314, database is CAplus and MEDLINE.

Substituting a carbon atom with a nitrogen atom (nitrogen substitution) on an aromatic ring in our leads I and II (X⁸ = X⁹ = CH) by applying nitrogen scanning afforded a set of compounds that improved not only the solubility but also the metabolic stability. The impact after nitrogen substitution on interactions between a derivative and its on- and off-target proteins (Raf/MEK, CYPs, and hERG channel) was also detected with most of them contributing to weaker interactions. After identifying the positions that kept inhibitory activity on HCT116 cell growth and Raf/MEK, compound II (X⁸ = X⁹ = N) (CH5126766/RO5126766) was selected as a clin. compound A phase I clin. trial is ongoing for solid cancers.

ACS Medicinal Chemistry Letters 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, Synthetic Route of 18437-58-6.

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

Lee, Li-Chen published the artcileFunctionalized polymer-supported pyridine ligands for palladium-catalyzed C(sp³)-H arylation, Application In Synthesis of 18437-58-6, the publication is ACS Catalysis (2016), 6(8), 5245-5250, database is CAplus.

Palladium trifluoroacetate, ligated to polymer-anchored 2-methylpyridine ligands, catalyzed C(sp³)-H bond activation and arylation of N-phthalimido-L-alaninamide with iodoarenes ArI, giving monoarylated products, ArCH₂CH(NPhth)CONHAr^F (2, Phth = 1,2-(CO)₂C₆H₄, Ar^F = 4-CF₃C₆H₄). The use of ligands to tune the reactivity and selectivity of transition-metal catalysts for C(sp³)-H bond activation is a current central challenge. One of us previously developed an uncommon example of a homogeneous catalyst that performs controlled C(sp³)-H arylation using pyridine derivatives as ligands, along with Pd [Science, 2014, 343, 1216-1220]. In this work, we report a functionalizable and tunable polymer support used in the immobilization of pyridine derivatives that yields a soluble, polymeric ligand platform facilitating C(sp³)-H activation reactions with good yields, selectivities differing from the homogeneous catalyst, and recovery of Pd. Unlike the homogeneous system, the supported catalysts in Pd-catalyzed C-H monoarylation reactions respond sensitively to the steric hindrance of the coupling partners.

ACS Catalysis 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, Application In Synthesis of 18437-58-6.

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

Hallinan, E. A. published the artcile2,4-Disubstituted oxazoles and thiazoles as latent pharmacophores for diacylhydrazine of SC-51089, a potent PGE₂ antagonist, Recommanded Product: 4-Amino-2-picoline, the publication is Bioorganic & Medicinal Chemistry (2001), 9(1), 1-6, database is CAplus and MEDLINE.

8-Chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(4-pyridinyl)propyl]hydrazide, monohydrochloride (SC-51089) is a functional PGE₂ antagonist selective for the EP₁ receptor subtype with antinociceptive activity. Analogs of SC-51089, in which the diacylhydrazine moiety has been replaced with 2,4-disubstituted-oxazoles and-thiazoles, are described. The analgesic activity seen among the oxazoles does not correlate with its PGE₂ antagonism.

Bioorganic & 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

Kato, Tetsuzo published the artcileSynthesis of methylpyridine derivatives. X. The Skraup reaction of 4-aminomethylpyridine 1-oxides, Formula: C6H8N2, the publication is Pharmaceutical Bulletin (1956), 178-81, database is CAplus and MEDLINE.

To prepare the rare 1,6-naphthyridine 6-oxide (I) derivatives, the Skraup reaction was applied to the easily available 4-amino-2,6-lutidine 1-oxide (II), 4-amino-3-picoline 1-oxide (III), 4-amino-2-picoline 1-oxide (IV), and 4-aminopyridine 1-oxide (V). Adding 2.75 g. concentrated H₂SO₄ dropwise to 1.38 g. II, 1.38 g. As₂O₅, and 3.68 g. glycerol, heating the mixture 3 hrs. in an oil bath at 155°, cooling, adding 50 cc. ice H₂O, making alk. with Na₂CO₃, and extracting with 200 cc. CHCl₃ yielded from the decolorized CHCl₃ extract 0.15 g. 5,7-di-Me derivative (VI) of I, white needles, m. 127-32° (from C₆H₆ or Me₂CO); picrate, yellow needles, m. 194-6° (from MeOH). Similar treatment gave (g. starting material, g. derivative of I formed, nature of crystals, m.p., and m.p. of picrate given): 3 g. III, 0.2 g. 8-Me (VII), white needles, 187-8.5° (from Me₂CO), 170-2°; 12.4 g. IV, 0.85 g. 7(or 5)-Me (VIII), white needles, 158-9° (from C₆H₆, 216-19° (decomposition); 1.1 g. V, 0.09 g. I, pale yellow needles, 151° (from C₆H₆ or Me₂CO), 185-6°. IV, m. 122-8° (picrate, m. 180°; HCl salt, m. 192°), and V, m. 229° (picrate, m. 201.5-2.0°), were prepared according to K. and H. (preceding abstract) from 4-nitro-2-picoline 1-oxide and 4-nitro-pyridine 1-oxide by catalytic reduction with 50% Pd-C in H₂O in 92% and 88% yield, resp. The yields of all 4 derivatives of I were only 5-9%. Ultraviolet absorption curves were given for I-VIII.

Pharmaceutical Bulletin 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, Formula: C6H8N2.

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

Luo, Dexia published the artcileDesign, Synthesis, and Bioactivity of α-Ketoamide Derivatives Bearing a Vanillin Skeleton for Crop Diseases, Quality Control of 18437-58-6, the publication is Journal of Agricultural and Food Chemistry (2020), 68(27), 7226-7234, database is CAplus and MEDLINE.

A series of novel α-ketoamide derivatives bearing a vanillin skeleton were designed and synthesized. Bioactivity tests on virus and bacteria were performed. The results indicated that some compounds exhibited excellent antitobacco mosaic virus (TMV) activities, such as compound I exhibited an inactivation activity of 90.1% and curative activity of 51.8% and compound II exhibited a curative activity of 54.8% at 500μg mL^-1, which is equivalent to that of the com. ningnanmycin (inactivation of 91.9% and curative of 51.9%). Moreover, the in vitro antibacterial activity test illustrated that compounds showed much higher activities than com. thiodiazole copper, which could be used as lead compounds or potential candidates. The findings of transmission electron microscopy and mol. docking indicated that the synthesized compounds exhibited strong and significant binding affinity to the TMV coat protein and could obstruct the self-assembly and increment of TMV particles. This study revealed that α-ketoamide derivatives bearing a vanillin skeleton could be used as a novel potential pesticide for controlling the plant diseases.

Journal of Agricultural and Food 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, Quality Control of 18437-58-6.

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

Blake, James F. published the artcileDiscovery of 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine inhibitors of Erk2, Computed Properties of 18437-58-6, the publication is Bioorganic & Medicinal Chemistry Letters (2014), 24(12), 2635-2639, database is CAplus and MEDLINE.

The discovery and optimization of a series of tetrahydropyridopyrimidine based extracellular signal-regulated kinase (Erks) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent and selective inhibition of Erk2 and knockdown of phospho-RSK levels in HepG2 cells and tumor xenografts. Proliferation of HCT116 (K-RasG12D) and A375 (BRafV600E) cell lines was inhibited by compound (I) with EC50s of 0.74 and 0.39 μM, resp. Pharmacokinetic parameters of I are given.

Bioorganic & Medicinal Chemistry Letters 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, Computed Properties of 18437-58-6.

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

Yan, Qiao published the artcileA Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts, Safety of 4-Amino-2-picoline, the publication is Journal of Organic Chemistry (2017), 82(8), 4328-4335, database is CAplus and MEDLINE.

α-, β-, γ-, And δ-carboline and the β-carboline alkaloid harman were prepared using the Ullman coupling of 2-iodo-2-cyclohexenone with nitropyridinyl halides followed by reductive cyclization and palladium-catalyzed aromatization as the key steps. The structures of α-, β-, γ-, and δ-carboline and harman were determined by X-ray crystallog.

Journal of Organic 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 C10H13BrN2O2, Safety of 4-Amino-2-picoline.

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

Gellibert, F. published the artcileDesign of novel quinazoline derivatives and related analogues as potent and selective ALK5 inhibitors, Quality Control of 18437-58-6, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(8), 2277-2281, database is CAplus and MEDLINE.

Starting from quinazoline 3a, we designed potent and selective ALK5 inhibitors over p38MAP kinase from a rational drug design approach based on co-crystal structures in the human ALK5 kinase domain. The quinazoline 3d exhibited also in vivo activity in an acute rat model of DMN-induced liver fibrosis when administered orally at 5 mg/kg (bid).

Bioorganic & Medicinal Chemistry Letters 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, Quality Control of 18437-58-6.

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

Chen, Ying-Chu published the artcileC-N Coupling of DNA-Conjugated (Hetero)aryl Bromides and Chlorides for DNA-Encoded Chemical Library Synthesis, Recommanded Product: 4-Amino-2-picoline, the publication is Bioconjugate Chemistry (2020), 31(3), 770-780, database is CAplus and MEDLINE.

DNA-encoded chem. library (DECL) screens are a rapid and economical tool to identify chem. starting points for drug discovery. As a robust transformation for drug discovery, palladium-catalyzed C-N coupling is a valuable synthetic method for the construction of DECL chem. matter; however, currently disclosed methods have only been demonstrated on DNA-attached (hetero)aromatic iodide and bromide electrophiles. We developed conditions utilizing an N-heterocyclic carbene-palladium catalyst that extends this reaction to the coupling of DNA-conjugated (hetero)aromatic chlorides with (hetero)aromatic and select aliphatic amine nucleophiles. In addition, we evaluated steric and electronic effects within this catalyst series, carried out a large substrate scope study on two representative (hetero)aryl bromides, and applied this newly developed method within the construction of a 63 million-membered DECL.

Bioconjugate 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

Deady, Leslie W. published the artcileThe aminolysis of p-nitrophenyl acetate by aminopyridines. Mechanisms in aqueous and aprotic solvents, Formula: C6H8N2, the publication is Australian Journal of Chemistry (1980), 33(11), 2441-6, database is CAplus.

In Me₂SO, the aminolysis of p-nitrophenyl acetate by aminopyridines results in amide formation, through nucleophilic catalysis by the ring N for 4-aminopyridine, but by direct amino N attack for 2-aminopyridine (as previously found for Ac₂O). In water, the aminopyridines catalyze the hydrolysis of the ester (unlike aniline, which still gives acetanilide). In general, this occurs by nucleophilic catalysis by the ring N. Even 4-amino-2-methylpyridine reacts by this route (though 2-picoline does not) and, of the compounds studied, only for 2-amino-6-methylpyridine does general base catalysis occur instead. Reasons for these mechanism changes are discussed.

Australian Journal of 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, Formula: C6H8N2.

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