Category: 18437-58-6

Morimoto, Nobuyuki published the artcileThe Design of Sulfobetaine Polymers with Thermoresponsiveness under Physiological Salt Conditions, Name: 4-Amino-2-picoline, the publication is Macromolecular Chemistry and Physics (2020), 221(5), 1900429, database is CAplus.

Thermoresponsive polymers are attractive in terms of basics and applications because of the phase separation in aqueous solution Some sulfobetaine polymers are known for their antifouling biocompatibility and upper critical solution temperature (UCST) type thermoresponsiveness; however, thermoresponsiveness disappears in aliphatic sulfobetaine polymers in physiol. salt conditions. Aromatic cation-containing sulfobetaine polymers are not responded because of the strong intermol. interactions. In this study, new sulfobetaine methacrylamides with a pyridinium cation, 3-(4-(2-methacrylamido)alkyl pyridinio-1-yl)propane-1-sulfonates, (PySMAAm)s, are designed and then prepared the homopolymers using aqueous reversible addition-fragmentation chain transfer polymerization The P(PySMAAm)s exhibited UCST-type thermoresponsiveness that is induced by substitution of the dipole-dipole interaction between the interpolymer side chain to an ion-dipole interaction in physiol. salt conditions. The thermoresponsiveness is affected by the mol. weight and structure of the side chains. Such sulfobetaine polymers can be promising tools as biomaterials especially for drug delivery and regenerative medicine.

Macromolecular Chemistry and Physics 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, Name: 4-Amino-2-picoline.

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

Miller, Laura C. published the artcileDevelopment of Potent Inhibitors of Pyocyanin Production in Pseudomonas aeruginosa, Recommanded Product: 4-Amino-2-picoline, the publication is Journal of Medicinal Chemistry (2015), 58(3), 1298-1306, database is CAplus and MEDLINE.

The development of new approaches for the treatment of antimicrobial-resistant infections is an urgent public health priority. The Pseudomonas aeruginosa pathogen, in particular, is a leading source of infection in hospital settings, with few available treatment options. In the context of an effort to develop antivirulence strategies to combat bacterial infection, we identified a series of highly effective small mols. that inhibit the production of pyocyanin, a redox-active virulence factor produced by P. aeruginosa. Interestingly, these new antagonists appear to suppress P. aeruginosa virulence factor production through a pathway that is independent of LasR and RhlR.

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

Kato, Tetsuzo published the artcileReaction of chloropicoline 1-oxides in liquid ammonia in the presence of potassium amide, Name: 4-Amino-2-picoline, the publication is Heterocycles (1973), 1(3-4), 233-6, database is CAplus.

3-Chloro-2-picoline 1-oxide was treated with K-NH3 at -33° and the product reduced with Raney Ni to give 4-amino-2-picoline. 4-Chloro-2-picoline 1-oxide similarly gave 3-amino-2-picoline and 4-amino-2-picoline. The products resulted from an intermediate 3,4-pyridyne 1-oxide. 5-Chloro-2-picoline 1-oxide, 6-chloro-2-picoline 1-oxide, 3-chloro-4-picoline 1-oxide, and 2-chloro-4-picoline-1-oxide underwent similar aminations.

Heterocycles 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, Name: 4-Amino-2-picoline.

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

Papillon, Julien P. N. published the artcileDiscovery of Orally Active Inhibitors of Brahma Homolog (BRM)/SMARCA2 ATPase Activity for the Treatment of Brahma Related Gene 1 (BRG1)/SMARCA4-Mutant Cancers, Synthetic Route of 18437-58-6, the publication is Journal of Medicinal Chemistry (2018), 61(22), 10155-10172, database is CAplus and MEDLINE.

SWI/SNF-related, matrix-associated, actin-dependent regulator of chromatin subfamily A member 2 (SMARCA2), also known as Brahma homolog (BRM), is a Snf2-family DNA-dependent ATPase. BRM and its close homolog Brahma-related gene 1 (BRG1), also known as SMARCA4, are mutually exclusive ATPases of the large ATP-dependent SWI/SNF chromatin-remodeling complexes involved in transcriptional regulation of gene expression. No small mols. have been reported that modulate SWI/SNF chromatin-remodeling activity via inhibition of its ATPase activity, an important goal given the well-established dependence of BRG1-deficient cancers on BRM. Here, the authors describe allosteric dual BRM and BRG1 inhibitors that downregulate BRM-dependent gene expression and show antiproliferative activity in a BRG1-mutant-lung-tumor xenograft model upon oral administration. These compounds represent useful tools for understanding the functions of BRM in BRG1-loss-of-function settings and should enable probing the role of SWI/SNF functions more broadly in different cancer contexts and those of other diseases.

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, Synthetic Route of 18437-58-6.

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

Arnold, Eric P. published the artcileOxidative Cyclization Approach to Benzimidazole Libraries, COA of Formula: C6H8N2, the publication is ACS Combinatorial Science (2020), 22(1), 1-5, database is CAplus and MEDLINE.

An efficient approach to the parallel synthesis of benzimidazoles from anilines is described. Library approaches to vary the N1 and C2 vectors of benzimidazoles are well established; however, C4-C7 variation has traditionally relied on 1,2-dianiline building blocks, providing limited chem. space coverage. We have developed an amidine formation/oxidative cyclization sequence that enables anilines as a diversity set for benzimidazole C4-C7 SAR generation in parallel format. The amidine annulation was achieved using PIDA or Cu-mediated oxidation to access both N-H and N-alkyl benzimidazoles. This library protocol has now been utilized for analog production in four medicinal chem. projects. Addnl., the synthesis of aza-benzimidazoles from aminopyridines was achieved via an analogous sequence.

ACS Combinatorial Science 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, COA of Formula: C6H8N2.

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

Walker, Gordon N. published the artcileApplication of sodium borohydride reduction to synthesis of substituted aminopiperidines, aminopiperazines, aminopyridines, and hydrazines, Safety of 4-Amino-2-picoline, the publication is Journal of Organic Chemistry (1961), 2740-7, database is CAplus.

Quaternization of 4-aminopyridine (I) with alkyl and arylalkyl halides gave 4-aminopyridinium salts, which were reduced with NaBH₄ to 1-(alkyl or arylalkyl)-4-aminopiperidines. Both 1-alkyl-4-aminopiperidines and 1-alkyl-4-aminopiperazines could be converted to Schiff bases, which were reduced with NaBH₄ to the corresponding secondary amines. Similar reduction of appropriate Schiff bases as a means of preparing substituted 3-aminopiperidines, aminopyridines, and aminomethylpyridines, as well as reduction of dialkylhydrazones to the corresponding trisubstituted hydrazines were also described. Anhydrous HBr was passed through a cold solution of 33.6 g. veratryl alc. in 500 mL. C₆H₆ 10 min., the lower layer separated, the C₆H₆ treated with Na₂CO₃, stirred, the solution of veratryl bromide (II) filtered, and used in the following step without purification To the C₆H₆ solution of II was added 19 g. I; the mixture refluxed 1.5 h., filtered, and the product crystallized gave 54 g. 1-(3,4-dimethoxybenzyl)-4-aminopyridinium bromide (IIa), m. 248-50° (decomposition), (alc.). A simple two-step synthesis was used in the preparation of the 1,2-diphenylethyl- and 3,4-dimethoxyphenacyl-substituted compounds The remaining substances were prepared from the com. available bromo (in one case, iodo) compounds by the same procedure with a few modifications in solvents used and reaction times. In reactions involving α,ω-dibromoalkanes, a mixture of the compound, 2 equivalents I, and a suitable amount of PhMe was refluxed. The product often settled as an oil. In this case the supernatant was decanted, and the oil crystallized 2-Methyl-4-aminopyridine (III) was most conveniently synthesized by a 2-step reduction of 4-nitro-2-picoline N-oxide as follows. (A) The oxide (45 g.) in 200 mL. alc. containing 4 g. 10% Pd-C shaken under H at 45 lb./sq. in. gave 33 g. 2-methyl-4-aminopyridine N-oxide (IV), yellow crystals, m. 181-3° (alc.). IV (30 g.) in 300 mL. 1:1 AcOH-H₂O treated with excess Zn dust, the mixture warmed 1 h., cooled, covered with Et₂O, treated with a 40% solution of 500 g. NaOH, and the Et₂O solution evaporated gave 16.8 g. III, m. 95° (cyclohexane). The following (4-H₂NC₅H₄N)RBr were obtained (R, solvent prepared in, reflux time in hrs., % yield, and m.p. given): EtO₂CCH₂, C₆H₆-alc., 1.5, 92, 197°; EtO₂CCH₂CH₂, PhMe, 5, 73, 159°; HOCH₂CH₂, PhMe, 3.5, 80, 131°; PhCH₂, C₆H₆, 0.5, 90, 196°; Ph₂CH, PhMe, 3, 56, 263°; PhCH₂CH₂, PhMe, 2, 77, 260°; PhCH₂CHPh, C₆H₆, 9, 53, 245°; PhOCH₂CH₂, PhMe, 4.5, 75, 184°; BzCH₂, C₆H₆, 2, 96, 308°; 3,4-(MeO)₂C₆H₃COCH₂, C₆H₆-alc., 0.3, 64, 271°; p-O₂NC₆H₄CH₂, PhMe, 5.5, 66, 266°; 2,4-(O₂N)₂C₆H₃, PhMe, 1, 56, 294°. The following [4-H₂NC₅H₄N(CH₂)_nNC₅H₄-4]Br₂ were similarly obtained (n, solvent, reflux time, % yield, and m.p. of product given): 4, PhMe, 2, 87, 273°; 6, PhMe, 14, 91, 303°; 8, PhMe, 5.5, 84, 300°; 9, PhMe, 5, 14, 221°; 10, PhMe, 5, 88, 247°; 11, PhMe, 7.5, 48, 216°; 12, PhMe, 13, 29, 209°; 16, PhMe (prepared from alkyl iodide), 11, 94, 185°. The following [2,4-Me(H₂N)C₅H₄N(CH₂)_nNC₅H₄(NH₂)Me- 4,2]Br₂ were obtained (n, solvent, reflux time in hrs., % yield, and m.p. given): 8, PhMe, 8, 60, 304°; 9, PhMe, 9, 17, 275°. IIa (30 g.) in 700 mL. MeOH treated in 1 h. with 250 g. NaBH₄, the mixture heated on a steam bath, cooled, treated with 500 mL. H₂O, covered with 2 l. Et₂O, the 2 phases treated with anhydrous K₂CO₃ to convert the lower layer to a paste, the Et₂O separated, evaporated, the 20 g. oil dissolved in 30 mL. alc., and treated with dry HCl gave 12.2 g. 1-(3,4-dimethoxybenzyl)-4-aminopiperidine-2HCl, m. 223-5° (decomposition) (MeOH-Et₂O). Other 4-aminopiperidines were obtained from the resp. quaternary salts by the same procedure. The free bases were hygroscopic oils. The amines had to be salted out with NaCl. When 4-aminopiperidines, as free bases, were required for further work, they were used directly in the crude state. 1-Methyl-4-aminopiperidine and 1-(β-hydroxyethyl)-4-aminopiperidine, both formed hygroscopic salts with HCl. The following 4-(N-substituted-amino)piperidine-2HCl were thus obtained (R, % yield, and m.p. given): EtO₂CCH₂, 17, 169°; PhCH₂, 41, 255°; PhCH₂CH₂, 88, 321°; PhCH₂CHPh, 40, 237° (decomposition); PhOCH₂CH₂, 44, 220°; PhCH(OH)CH₂, 90, 248° (decomposition); 3,4-(MeO)₂C₆H₃CH(OH)CH₂, 56, 220° (decomposition); p-O₂NC₆H₄CH₂, 10, 265° (decomposition). The following 4-H₂NC₅H₄N(CH₂)_nNC₅H₄NH₂-4.4HCl were similarly obtained (n, % yield, and m.p. given): 6, 22, 204°; 10, 16, 295°; 12, 34, 311°; 16, 20, 315°. 1,10-Bis(4-amino-1-piperidyl)decane was also characterized by preparation of the bis(dichloroacetate)-2HCl, m. 227-30° (decomposition) (alc.). 1-Methyl-4-aminopiperazine (8.1 g.) and 11.2 g. veratraldehyde in 200 mL. PhMe refluxed 1.5 h., evaporated, the residue dissolved in 150 mL. MeOH, the solution reduced with 40 g. NaBH₄, heated 0.5 h. on the steam bath, and the 20.5 g. yellow oil treated with alc. HCl gave 10 g. 1-methyl-4-(3,4-dimethoxybenzylamine)piperazine, m. 199-202° (decomposition). Other secondary aminopiperidines and aminopiperazines were given in a table. Attempts to reduce imines derived from 1-phenyl-2-propanone and 1-substituted 4-aminopiperidines with NaBH₄ did not lead to desired products, probably because of cleavage of the unstable imines. 3-Aminopyridine (16.8 g.) and 30 g. veratraldehyde in 500 mL. xylene refluxed 24 h. and the 45.5 g. residual oily imine in MeOH reduced with NaBH₄ gave 33 g. 3-(3,4-dimethoxybenzylamino)pyridino (V), m. 123-5° (MeOH). The other pyridines were similarly prepared The following RNHR’ were thus obtained (R, R’, % yield, and m.p. given): 3,4- dimethoxybenzyl, 1-methyl-4-piperidyl, 60, 254-6° (decomposition); 3,4,5-trimethoxybenzyl, 1-methyl-4-piperidyl, 37, 264-5° (decomposition); 3,4-dimethoxybenzyl, 1-(β-hydroxyethyl)-4-piperidyl, 12, 255-6° (decomposition); 4-methoxybenzyl, 1-(3,4-dimethoxybenzyl)-4-piperidyl, 46, 274-5° (decomposition); 3,4,5-trimethoxybenzyl, 1-methyl-4-piperazyl, 56, 135-7°; p-dimethylaminobenzyl, 1-methyl-4-piperazyl, 40, 125-7° (157-60°); 3-pyridylmethyl, 1-methyl-4-piperazyl, 95, 201-2° (220-6° with 0.5H₂O); 1-hydroxy-1-phenyl-2-Pr, 1-methyl-4-piperazyl, 25, 219-21° (decomposition); 3,4-dimethoxybenzyl, 2-pyridyl, 65, 102-3°; 3,4,5-trimethoxybenzyl, 2-pyridyl, 45, 167-8°; p-dimethylaminobenzyl, 2-pyridyl, 52, 125-6°; 3,4,5-trimethoxybenzyl, 3-pyridyl, 63, 109-10°; 3,4,5-trimethoxybenzyl, 3-pyridylmethyl, 90, 205-7°; p-dimethylaminobenzyl, 3-pyridylmethyl, 96, 185-6° (decomposition); 3,4-dimethoxybenzyl, 4-pyridylmethyl, 22, 200° (decomposition); 3,4,5-trimethoxyhenzyl, 4-pyridylmethyl, 43, 214-16°; p-dimethylaminobenzyl, 4-pyridylmethyl, 45, 195-6°; 1-phenyl-2-Pr, 3-pyridylmethyl, 55, 205-7°; 1-phenyl-2-Pr, 4-pyridylmethyl, 80, 181-3°; 3,4,5-trimethoxybenzyl, NMe₂, 45, 81-3; p-dimethylaminobenzyl, NMe₂, 7, 158-61° (decomposition); 1-phenyl-2-Pr, NMe₂, 70, 123-5°; 1,2-diphenylethyl, NMe₂, 23, 183-5°; PhCH:CHCHMe, NMe₂, 5, 117-20° (decomposition). V (14.1 g.) converted rapidly to the MeI salt, evaporated, the crystals suspended in 200 mL. MeOH, reduced with 125 g. NaBH₄, and the residual oil treated with HCl gave 14.6 g. 1-methyl-3-(3,4-dimethoxybenzylamino)piperidine-2HCl, m. 233-5° (decomposition). 3-Aminopiperidine (7.6 g.), 12.7 g. veratraldehyde, and 250 mL. PhMe refluxed 3.5 h., the crude imine reduced with NaBH₄ in alc., and crystallized gave 20.6 g. V.2HCl, m. 229-31° (alc.). Reduction of p-dimethylaminobenzylidene derivative and isolation gave 76% 3-(4-dimethylaminobenzylamino)piperidine, no definite m.p. 3-(3-Pyridylmethylamino)piperidine was obtained in 79% yield by reduction of the 3-pyridylidene derivative and isolated as the tri-HCl salt. Veratraldehyde (16.3 g.) and 6.5 g. N,N-dimethylhydrazine mixed, the oil taken up in 200 mL. C₆H₆, the solution refluxed 4 h., evaporated, and the hydrazone reduced in MeOH with NaBH₄ gave 13.9 g. N,N-dimethyl-N-(3,4-dimethoxybenzyl)hydrazine-HCl, m. 172-4.5°. The other hydrazine derivatives above were prepared by the same method.

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 C12H9NO, Safety of 4-Amino-2-picoline.

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

Ladjarafi, Abdelkader published the artcileA DFT study of the tautomeric equilibria of substituted pyridone-like derivatives: Sulphur versus oxygen and imino effect, Formula: C6H8N2, the publication is Journal of Molecular Structure: THEOCHEM (2004), 709(1-3), 129-134, database is CAplus.

Several pyridone-like compounds, where the extracyclic oxygen atom has been replaced by a sulfur atom or an imino NH group, have been studied using B3LYP/6-311 + G** calculations We found that the NH substituted species differ from the other ones: a single tautomeric form, i.e. the aminopyridine one, strongly dominates either in the gas phase or in the presence of a polar solvent like DMSO. In the gas phase or in solution, pyridinethiol species are more favored than the pyridinol ones relatively to their corresponding tautomers. The zero point vibration energy and the entropic contribution to the free energy of the reaction play a more determining role for the sulfur containing species.

Journal of Molecular Structure: THEOCHEM 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

Matralis, Alexios N. published the artcileDevelopment of Chemical Entities Endowed with Potent Fast-Killing Properties against Plasmodium falciparum Malaria Parasites, Related Products of pyridine-derivatives, the publication is Journal of Medicinal Chemistry (2019), 62(20), 9217-9235, database is CAplus and MEDLINE.

One of the attractive properties of artemisinins is their extremely fast-killing capability, quickly relieving malaria symptoms. Nevertheless, the unique benefits of these medicines are now compromised by the prolonged parasite clearance times and the increasing frequency of treatment failures, attributed to the increased tolerance of Plasmodium falciparum to artemisinin. This emerging artemisinin resistance threatens to undermine the effectiveness of antimalarial combination therapies. Herein, we describe the medicinal chem. efforts focused on a cGMP-dependent protein kinase (PKG) inhibitor scaffold, leading to the identification of novel chem. entities with very potent, similar to artemisinins, fast-killing potency against asexual blood stages that cause disease, and activity against gametocyte activation that is required for transmission. Furthermore, we confirm that selective PKG inhibitors have a slow speed of kill, while chemoproteomic anal. suggests for the first time serine/arginine protein kinase 2 (SRPK2) targeting as a novel strategy for developing antimalarial compounds with extremely fast-killing properties.

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, Related Products of pyridine-derivatives.

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

Shkurko, O. P. published the artcileSubstituent effects on the amino-group chemical shifts in NMR spectra of substituted aminopyridines, Formula: C6H8N2, the publication is Khimiya Geterotsiklicheskikh Soedinenii (1990), 54-9, database is CAplus.

Correlation analyses are presented for amino-group proton chem. shifts in m– and p-substituted (with respect to the amino group) 2-, 3-, and 4-aminopyridines (6 series altogether) using inductive and resonant substituent constants

Khimiya Geterotsiklicheskikh Soedinenii 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 C7H5ClN2S, Formula: C6H8N2.

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

Ojha, K. G. published the artcileSynthesis and antibacterial activity of some substituted phenothiazin-3-ones, Related Products of pyridine-derivatives, the publication is International Journal of Chemical Sciences (2003), 1(4), 347-350, database is CAplus.

1,2,4-Trihalophenothiazin-3-ones were prepared by condensing 2-aminobenzenethiols with chloranil/bromanil in 1:1 molar ratio. These compounds on refluxing with aryl amine and anhydrous NaOAc in EtOH gave substituted 2-arylaminophenothiazin-3-ones, which exhibited antibacterial activity.

International Journal of Chemical Sciences 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, Related Products of pyridine-derivatives.

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