Category: 18437-58-6

He, Dian published the artcileDesign, Synthesis and Activity Evaluation of N-(pyridin-4-yl) Salicylamides as Antimycobacterial Agents, Computed Properties of 18437-58-6, the publication is Asian Journal of Chemistry (2014), 26(21), 7269-7275, 7 pp., database is CAplus.

A series of N-(pyridin-4-yl) salicylamides derivatives I (R¹ = H, Cl, CH₃; R² = R⁴ = H, Cl; R³ = H, Cl, CF₃; R⁵ = H, OCH₃; R⁶ = H, Cl, Br, CF₃) were prepared through acylation of the corresponding acetylsalicyloyl chlorides with substituted 4-aminopyridines. The compounds I were evaluated in vitro for antimycobacterial activities against Mycobacterium tuberculosis (TB) and Mycobacterium avium (A) by the min. inhibitory concentrations (MIC) values. Eight of the compounds I exhibited lower MIC against Mycobacterium avium than the one of isoniazide, meanwhile, four of the compounds I exhibited good anti-TB activity compared to isoniazide. Antimycobacterial activities of compounds I were influenced by the balance between hydrophobicity and electron withdrawing substituent effects on the Ph and pyridine ring.

Asian 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, Computed Properties of 18437-58-6.

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

Yang, Wenqing published the artcileDesign, Synthesis, Antifungal and Antibacterial Activities of N-phenyl and N-pyridinyl-5-(trifluoromethyl)-pyrazole-4-carboxamide Derivatives, Recommanded Product: 4-Amino-2-picoline, the publication is Journal of Heterocyclic Chemistry (2018), 55(10), 2261-2269, database is CAplus.

A series of N-Ph and N-pyridinyl-5-(trifluoromethyl)-pyrazole carboxamides, compounds I [R = Ph, 2-pyridinyl, 2-fluoro-4-pyridinyl, etc.] were designed and synthesized. Bioassay results indicated that antifungal and antibacterial activities of title compounds could be obviously improved by placing trifluoromethyl on the 5-position of the pyrazole ring and substituted 4-pyridinyl at the amine side of the amide bond. The EC₅₀ values of compound I [R = 4-pyridinyl] against Gibberella zeae, Cytospora mandshurica, and Fusarium oxysporum were 14.7, 21.1, and 32.7 μg/mL, resp., better than hymexazol (30.2, 47.3, and 42.5 μg/mL) and carboxin (34.2, >200, and >200 μg/mL). And the EC₅₀ values of compounds I [R = 2-fluoro-4-pyridinyl, 2,6-dichloro-4-pyridinyl, 3,5-dichloro-4-pyridinyl, 6-methyl-2-pyridinyl, 2-methylphenyl, 2-fluorophenyl, 4-chlorophenyl and 4-methoxyphenyl] against rice bacterial leaf blight were 17.0, 21.8, 21.9, 18.6, 16.8, 25.9, 9.4, and 24.4 μg/mL, resp., much better than bismerthiazol (70.5 μg/mL).

Journal of Heterocyclic 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 C9H21NO3, Recommanded Product: 4-Amino-2-picoline.

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

Yuan, Xinrui published the artcileDesign, synthesis and biological evaluation of pyridone-aminal derivatives as MNK1/2 inhibitors, Computed Properties of 18437-58-6, the publication is Bioorganic & Medicinal Chemistry (2019), 27(7), 1211-1225, database is CAplus and MEDLINE.

Excessive phosphorylation of eukaryotic translation initiation factor 4E (eIF4E) plays a major role in the dysregulation of mRNA translation and the activation of tumor cell signaling. eIF4E is exclusively phosphorylated by mitogen-activated protein kinase interacting kinases 1 and 2 (MNK1/2) on Ser209. So, MNK1/2 inhibitors could decrease the level of p-eIF4E and regulate tumor-associated signaling pathways. A series of pyridone-aminal derivatives were synthesized and evaluated as MNK1/2 inhibitors. Several compounds exhibited great inhibitory activity against MNK1/2 and selected compounds showed moderate to excellent anti-proliferative potency against hematol. cancer cell lines. In particular, compound 42i (MNK1 IC₅₀ = 7.0 nM; MNK2 IC₅₀ = 6.1 nM) proved to be the most potent compound against TMD-8 cell line with IC₅₀ value of 0.91 μM. Furthermore, 42i could block the phosphorylation level of eIF4E in CT-26 cell line, and 42i inhibited the tumor growth of CT-26 allograft model significantly. These results indicated that compound 42i was a promising MNK1/2 inhibitor for the potent treatment of colon cancer.

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 C8H6BrClO, Computed Properties of 18437-58-6.

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

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

Shang, Ming published the artcileCu(II)-Mediated C-H Amidation and Amination of Arenes: Exceptional Compatibility with Heterocycles, Computed Properties of 18437-58-6, the publication is Journal of the American Chemical Society (2014), 136(9), 3354-3357, database is CAplus and MEDLINE.

A Cu(OAc)₂-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.

Journal of the American Chemical Society 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 C2H3N3, Computed Properties of 18437-58-6.

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

Ochiai, Eiji published the artcilePolarization of aromatic heterocyclic compounds. CV. 4-Substituted derivatives of α-picoline, Application of 4-Amino-2-picoline, the publication is Pharmaceutical Bulletin (1954), 147-9, database is CAplus.

cf. C.A. 48, 10746c. PCl₃ (10 g.) added portionwise with ice cooling to 10 g. 4-nitro-α-picoline N-oxide in 200 ml. of CHCl₃, the mixture warmed at 50° for 10 min., cooled, poured onto ice, neutralized with Na₂CO₃, extracted with CHCl₃, dried over Na₂SO₄, and evaporated gave 7 g. 4-nitro-α-picoline (I), m. 42-5° (from petr. ether). I (1 g.) dissolved in MeOH and reduced over Pd-C gave 4-amino-α-picoline, purified through the picrate, m. 193°. 4-Bromo-α-picoline (II) (picrate, m. 184-5°) was prepared by 4 methods: (1) I (1 g.) heated at 150-70° for 8 hrs. with 5 g. 48% HBr, the mixture evaporated under reduced pressure, alkalinized with Na₂CO₃, extracted with Et₂O, dried over Na₂SO₄ and evaporated gave 0.2 g. II, an oily residue, which was converted to the picrate. (2) I (5 g.), 26 g. of (H₂N)₂CO and 30 ml. 48% HBr refluxed 7 hrs., diluted with H₂O, alkalinized with Na₂CO₃, steam distilled, the distillate saturated with NaCl, extracted with Et₂O, the Et₂O extract dried over Na₂SO₄, the Et₂O removed, and the residue distilled gave 1.2 g. II, b₅ 47-56°. (3) I (3 g.) and 5 ml. AcBr heated 6 hrs. on a water bath (a red color developed), the mixture evaporated in vacuo, diluted with H₂O, alkalinized with Na₂CO₃, and extracted with Et₂O, and the extract distilled gave 1.2 g. II. (4) 4-Hydroxy-α-picoline N-oxide (10 g.) in 60 ml. CHCl₃ cooled and treated portionwise with 25 g. PBr₃ in 20 ml. CHCl₃; after the reaction subsided the mixture was refluxed 6 hrs. on a water bath and a sirupy mass precipitated The CHCl₃ layer extracted with H₂O, the sirupy residue treated with 200 ml. ice water, the aqueous solutions mixed, alkalinized with Na₂CO₃, steam distilled, the distillate saturated with NaCl, extracted with Et₂O, and the extract distilled in vacuo gave 7.8 g. II. CuCN (dried at 110° for 36 hrs.) (2.5 g.) added to 4.5 g. II, the mixture gradually heated to 150-60° when the mixture melted with darkening, the temperature raised to 180° then cooled to 120°, 1 g. CuCN added, the mixture heated 0.25 hrs. at 170-80° and distilled gave 2.2 g. 4-cyano-α-picoline (III), b_11-15 about 75°, m. 45.5-6.5° (from petr. ether); picrate, decompose 163-4° (from EtOH). III (1.5 g.) reduced over Pd-C in acid solution gave 1.6 g. 4-amino-αpicoline, decompose 274° (from MeOH); picrate, m. 195-6° (from MeOH); benzoate, m. 81-3° (from benzene).

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, Application of 4-Amino-2-picoline.

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

Ochiai, Eiji published the artcilePolarization of aromatic heterocyclic compounds. LXVI. Reduction of 4-nitro-2-picoline 1-oxide, Safety of 4-Amino-2-picoline, the publication is Yakugaku Zasshi (1947), 158-60, database is CAplus.

Reduction of 4-nitro-2-picoline 1-oxide (I) indicated that it also had certain peculiarities which were observed in the reduction of 4-nitropyridine 1-oxide (C.A. 45, 5151h). Catalytic reduction of I in 10% HCl with 60% Pd-charcoal gave a HCl salt of 4-amino-2-picoline 1-oxide (II), needles, m. 189-91°. Further reduction of the II.HCl in AcOH-Ac₂O with 60% Pd-charcoal gave 4-amino-2-picoline (III), slightly hygroscopic cubic crystals, m. 95°; picrate, m. 193°. Catalytic reduction of I to III did not proceed well in HCl and EtOH. Reduction of I in a mixture of H₂S-saturated NH₄OH and EtOH gave 4,4′-azo-2-picoline 1,1′-dioxide (IV), red needles, m. 224-5°. Reduction of I in 10% NaOH solution with NaNO₂ at about 45° gave IV and a small amount of recovered I. MeOH as a solvent gave 4-methoxy-2-picoline 1-oxide, rhomboprisms, m. 78-80°, and no azo compound was formed. Reduction of I in glacial AcOH, EtOH, and H₂O with Zn dust also gave IV, while reduction in glacial AcOH with Zn gave 4,4′-azoxy-2-picoline 1,1′-dioxide (V), orange-red crystals, m. 220-1°, and a small amount of recovered I. Reduction in EtOH-glacial AcOH with Zn gave chiefly V with a small amount of IV, and reduction in H₂O alone in a sealed tube gave V with recovery of I. Reduction in NaOH solution gave III. Since this reduction, when carried out on a water bath about 1 hr. gave only IV with recovery of I, the reduction was assumed to proceed via the azo compound Reduction of I in HCl with SnCl₂ gave IV, as well as III, while reduction in EtOH with Na₂S₂O₄ also gave III.

Yakugaku Zasshi 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, Safety of 4-Amino-2-picoline.

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

Petrow, V. published the artcileAnalgesics. II. Aryloxyalkyl oxaalkylamines, Recommanded Product: 4-Amino-2-picoline, the publication is Journal of Pharmacy and Pharmacology (1958), 86-95, database is CAplus and MEDLINE.

cf. C.A. 51, 8723b. Compounds formally related to aryloxypropanolamine in which the aryl and amine residues are joined by combinations derived from glycerol and ethylene glycol are synthesized. Adding 108 g. ο-cresol to 40 g. NaOH in 450 ml. EtOH and 40 ml. H₂O followed by 143 g. (ClCH₂CH₂)₂O and refluxing 5 hrs. formed an oil with fractons b_0.3 36-95° (52.4 g.), 100-20° (111.9 g.), and 160° (26.9 g.). The 2nd fraction yielded 5-ο-tolyloxy-3-oxapentyl chloride (I), b_0.3 92°, and the 3rd fraction yielded 1,5-bis-ο-tolyloxy-3-oxapentane, b_0.3 156°. I was heated with piperidine to form N-(5-ο-tolyloxy-3-oxapentyl)piperidine, b_0.3 130° (picrate, yellow nodules from EtOAc-ligroine, m. 77- 8°). N-(5-ο-Tolyloxy-3-oxapentyl)pyrrolidine, oil, b_0.3 122°; Δ³-piperideine analog, b_0.3 138° (picrate, yellow needles from EtOAc-ligroine, m. 92-4°). 3-Phenoxy-1,2-epoxy- propane and N-(2-hydroxyethyl)piperidine in C₆H₆ were refluxed 20 hrs. to form N-(5-hydroxy-6-phenoxy-3-oxahexyl)-piperidine, b_0.1. 150°; the 6-ο-methoxyphenoxy-3-oxahexyl analog b_0.1 160°. 2-ο-Tolyloxyethanol and 2,3-epoxypropyl chloride with polyphosphoric acid were heated at 100° for 20 hrs. to form 2-hydroxy-6-ο-tolyloxy-4-oxahexyl chloride, b_0.5 136°. 2-ο-Tolyloxyethanol was refluxed with NaOMe in MeOH for several min., the residual product was suspended in dry C₆H₆, 1-chloro-2,3-epoxypropane added, and the mixture refluxed 8 hrs. to yield from the main distillation fraction 1,2-epoxy-6-ο-tolyloxy-4-oxahexane (II) (oil, b_0.05 100°) and from the top fraction a viscous oil, b_0.07 210°. Treatment of the foregoing chlorohydrin with an equivalent of KOH in MeOH at 0° followed by dilution and extraction with CHCl₃ yielded II. II in C₆H₆ with Δ³-piperideine formed N-(2-hydroxy-6-ο-tolyloxy-4-oxahexyl)-Δ³-piperideine, b_0.3 162° [HCl salt, hygroscopic, m. 50-60°; picrate, m. 81-3° (EtOAc-Et₂O)]. 3-ο-Tolyloxy-1,2-epoxypropane and allyl alc. treated carefully with H₂SO₄ and heated at 100° for 2 hrs. yielded from the residual fraction b_0.25 120° 6-hydroxy-7-ο-tolyloxy-4-oxa-1-heptene (III), b_1.2 130-2°; the fraction b_0.25-1 124-44° contained a high proportion of 3-ο-tolyloxypropane-1,2-diol. 2-Hydroxy-3-ο-tolyloxypropyl chloride (100 g.) and 232 g. allyl alc. with 33.6 g. powd. KOH added in portions then heated at 100° for 8 hrs., diluted, and extracted with CHCl₃ yielded 97.8 g. III, b_0.1 113°. Adding 63 g. III to a cold solution of 39.15 g. perbenzoic acid in 995 ml. C₆H₆, keeping at 0° for 2 days and then room temperature for 2 days, and refractionating the fraction (37.7 g.), b_0.3 118-50°, yielded 1,2-epoxy-6-hydroxy-7-ο-tolyloxy-4-oxaheptane, b_0.4 144°, which condensed with Et₂NH in C₆H₆ to form N-(2,6-dihydroxy-7-ο-tolyloxy-4-oxaheptyl)diethylamine, b_0.3 174° (piperidine analog, b_0.4 194°). 6-Hydroxy-7-phenoxy-4-oxa-1-heptene b_0.05 110°. 1,2-Epoxy-6-hydroxy-7-phenoxy-4-oxaheptane b_0.4 140°. N-(2,6-Dihydroxy-4-oxahexyl)-p-anisidine, m. 65-7° (EtOAc-ligroine), refluxed 5 hrs. in MeOH with MeI and Na₂CO₃ formed N-methyl-N-(2,6-dihydroxy-4-oxahexyl)-p-anisidine, b_0.1 180°; the N-Et analog, b_0.1 185°. N-(2,6-Dihydroxy-4-oxahexyl)-p-phenetidine (by alk. condensation in MeOH), light yellow prisms, m. 70-2° (EtOAc-ligroine) [picrate, m. 127-8° (EtOH)]; N-Et derivative, _0.3 180°. N (2,6-Dihydroxy-4-oxahexyl)-p-propoxyaniline (61% yield) b_0.1 192-8°, light yellow needles, m. 71-3° (EtOAc-ligroine); p-butoxyaniline analog, b_0.4 195-200°, yellow needles, m. 69-71° (EtOAc-ligroine); ο-phenetidine analog, b_0.4 182-6°, pale yellow needles, m. 57-8° (EtOAc-ligroine); morpholine analog, b_0.5 144°; Δ³-piperideine analog, b_0.3, 140°; pyrrolidine analog, b_0.1 118°. N-(2,9-Dihydroxy-4,7-dioxanonyl)-p-phenetidine b_0.5 220°; picrate, bright yellow needles, m. 120-1° (EtOAc). N-(2,6-Dihydroxy-4-oxaheptyl)-p-phenetidine on fractionation (b_0.04-0.05 200-5°) gave a white solid (A), m. 102-4° (EtOAc-ligroine), soluble in hot H₂O; picrate, yellow fluffy needles, m. 130-2° (EtOAc). The concentrated mother liquors from A yielded a main fraction B, b_0.8 210°, m. 54-6° (Et₂O-ligroine), more soluble in cold H₂O than A. Tentative structures were for A, p-EtC₆H₄NHCH₂CH(OH)CH₂OCH₂CH(OH)Me, for B, p-EtC₆H₄NHCH₂CH(OH)CH₂OCHMeCH₂OH. The p-anisidine analog fractionated by b_0.5 200-20° yielded 2 isomers; the less soluble crystallized from H₂O [picrate, m. 134-6° (EtOAc-ligroine)]; the more soluble m. 64-6° (Et₂O-ligroine) [picrate, m. 12 6° (EtOAc-ligroine)]. Tentative structures were analogous to those of A and B. N-p-Ethoxyphenylmorpholine b_0.5 120°, m. 75-6° (EtOH-H₂O); HCl salt, m. 170-1° (EtOH-Et₂O). 3-(3,4,5-Trimethoxyphenyl)aminopropane-1,2-diol b_0.2 210°; HCl salt, white needles with blue-green tinge, m. 148-50° (EtOH-Et₂O). 4-ο-Tolyloxybut-2-yn-1-yl chloride b_0.3 110°. 1-Diethylamino-4-phenoxybut-2-yne, from 4-phenoxybut-2-yn-1-yl chloride and Et₂NH as the base, b_0.2 110-15°; HCl salt, m. 138-9° (EtOH-Et₂O). 1-Diethylamino-4-ο-tolyloxybut-2-yne b_0.6 126-8°; HCl salt, m. 116-17° (EtOH-Et₂O). 1-Δ³-Piperideino-4-ο-tolyloxybut-2-yne b_0.5 130°; HCl salt, m. 126-7° (iso-PrOH-Et₂O).

Journal of Pharmacy and Pharmacology 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 artcileMechanisms for the acetylation of aminopyridines, Related Products of pyridine-derivatives, the publication is Australian Journal of Chemistry (1978), 31(8), 1725-30, database is CAplus.

Rates of acetylation of aminopyridines and some ring methyl-substituted derivatives, with acetic anhydride in acetone at 36°, are reported. Rate-determining acetylation is directly at the amino nitrogen for all 2- and 3-aminopyridines studied. Reaction through a ring N-acetyl intermediate occurs for 4-aminopyridine but the presence of a 2-Me substituent blocks this pathway.

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, Related Products of pyridine-derivatives.

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