Tag: M.W=100-150

Barraclough, Paul published the artcileInotropic ‘A’ ring substituted sulmazole and isomazole analogs, Synthetic Route of 33631-04-8, the main research area is inotropic sulmazole isomazole analog; imidazopyridine preparation inotropic.

A series of “”A”” ring substituted sulmazole I [R = 4-, 5-, 6-MeO, 5-NO2, 5-Cl, 5-Me, 5-Ac; X = S, S(O), O] and isomazole analogs II [R = 2-, 5-, 6-MeO, 5-NH2, 5-NO2; X = S, S(O), O] were prepared and evaluated as inotropic agents. Thus, 5-methoxy-2,3-pyridinediamine was cyclized with 2-methoxy-4-(methylthio)benzoic acid to give I (R = 5-MeO, X = S), which was oxidized to give I [R = 5-MeO, X = S(O)]. PKA’s, protonation sites, and log P values were measured for selected compounds and their electronic properties were calculated No simple correlation between inotropic activity and pKA, protonation site, or log P value was observed However, in vitro inotropism did correlate with the calculated charge d. of the “”B”” ring imidazo nitrogen atom. The 6-position of sulmazole appeared to be the most tolerant toward substituents, the 6-amino derivative I [R = 6-NH, X = S(O)] being a more potent inotrope than sulmazole itself. 4-Methoxyisomazole had comparable in vivo inotropic properties to those of isomazole.

Journal of Medicinal Chemistry published new progress about Inotropics. 33631-04-8 belongs to class pyridine-derivatives, name is 2-Methoxypyridine-3,4-diamine, and the molecular formula is C6H9N3O, Synthetic Route of 33631-04-8.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Barlin, G. B. published the artcileIonization constants of heterocyclic substances. IX. Protonation of aminopyridines and aminopyrimidinones, Product Details of C6H9N3O, the main research area is pyridines aminohydroxy ionization UV; basicity pyridines aminohydroxy; aminohydroxypyridine ionization UV; pyrimidines aminohydroxy ionization UV; protonation aminohydroxypyridine.

Ionization constants and uv spectra are reported for amino-2-hydroxypyridines (amino-2-pyridones), amino-4-hydroxypyridines(amino-4-pyridones), and amino-2,4-di-hydroxypryimidines (amino-2,4-pyrimidinediones) and their O-and ring N-Me derivatives Protonation of 3- and 5-amino-2-hydroxypyridines and 3,4-diamino-2-hydroxypyridine (I) occurs first at the amino group (the 3-NH2 of I), but 4- and 6-amino-2-hydroxypyridines and 2- and 3-amino-4-hydroxypyridines are protonated first at O. The most basic center of 4,5-diamino-2,6-dihydroxypyrimidine is the 5-NH2 group.

Journal of the Chemical Society [Section] B: Physical Organic published new progress about Ionization. 33631-04-8 belongs to class pyridine-derivatives, name is 2-Methoxypyridine-3,4-diamine, and the molecular formula is C6H9N3O, Product Details of C6H9N3O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Trecourt, Francois published the artcileSynthesis of diazaxanthones: 5H-pyrano[2,3b:6,5-b’]dipyridin-5-one and 5H-thiopyrano[2,3-b:6,5-b’]dipyridin-5-one, Computed Properties of 71255-09-9, the main research area is pyranodipyridinone; thiopyranodipyridinone; formylation bromopyridine; pyridinecarboxaldehyde conformation.

The title compds (I; X = O, S, resp.) were prepared in 5 and 6 steps, resp., from 3-bromo-2-chloropyridine; yields were excellent. The CO bridge of the diazaxanthones was formed by coupling the aldehydes II (X = O) with 3-lithio-2-methoxypyridine and II (X = S) with 3-lithio-2-(methylthio)pyridine followed by oxidation of the resulting benzylic alc. The other bridge was formed by coupling the 2 ether or sulfide functions with pyridinium-HCl at ∼220°. The conformations of II (X = O, S) are discussed. II (X = O, S) were prepared by treatment of the 3-bromo analogs with BuLi and HCO2Et. I are the 1st reported xanthone-like heterocycles with 2 pyridine rings condensed to the 4-pyrone or -thiopyrone ring.

Journal of Chemical Research, Synopses published new progress about Cyclization. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, Computed Properties of 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Roy, Patrick J. published the artcileThe Hemetsberger-Knittel synthesis of substituted 5-, 6-, and 7-azaindoles, HPLC of Formula: 71255-09-9, the main research area is pyrrolo pyridine azaindole preparation cyclization thermolysis pyridinyl azido propenoate; azido pyridine acrylate preparation thermal cyclization Hemetsberger Knittel; Hemetsberger Knittel synthesis azaindole thermolysis cyclization template.

A series of substituted 5-, 6-, and 7-azaindoles were prepared via the Hemetsberger-Knittel reaction. In general, better yields were obtained at higher temperatures and shorter reaction times than required for the formation of the analogous indoles, and in some cases, only decomposition occurred below a min. temperature The resulting templates offer up to five sites for subsequent functionalization to allow a wide range of chem. diversity.

Synthesis published new progress about Cyclization. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, HPLC of Formula: 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Okuda, Shigenobu published the artcileThe constitution of matrine. XXVI. The constitution of dehydro-α-matrinidine, Safety of 4-Amino-2-picoline, the publication is Pharmaceutical Bulletin (1956), 257-61, database is CAplus.

cf. C.A. 49, 8316f. The decision between the 2 proposed structures of dehydro-α-matrinidine (I), upon which the structure of matrine depends, is based on spectrographic comparisons. Ultraviolet absorption maximum are recorded for: the degradation products of matrine, I, and the 2 bases C₁₂H₁₈N₂, m. 111° and 190°, resp.; the 4-aminopyridine group of 4-H₂N and 4-Et₂N derivatives of C₅H₅N, and 5,7-dimethyl-1,2,3,4-tetrahydro-1,6-naphthyridine (II); the 3-aminopyridine group of 3-H₂N (III) and 3-Me₂N (IV) derivatives of C₅H₅N, and 2,4-dimethyl-5,6,7,8-tetrahydro-1,5-naphthyridine (V); the 2-aminopyridine group of the 2-H₂N derivative of C₅H₅N, and 2,4-dimethyl-5,6,7,8-tetrahydro-1,8-naphthyridine. The solvents used were EtOH, 0.1N NaOH, 0.01N H₂SO₄, 50% H₂SO₄, and concentrated H₂SO₄. The spectra of 2,4-Me(H₂N) and 2,6,4-Me₂(H₂N) derivatives of C₅H₅N were determined in EtOH only. Only II and IV were previously unknown. The synthesis of II will be reported later. Methylation of III with H₂CO and HCO₂H gave IV, b₆ 95°; picrate, m. 179-81°. Study of the spectra led to the following generalizations: the 3-aminopyridine group form their di-salts even in 50% H₂SO₂, whereas the matrine products and the 4-aminopyridine group show the same absorption in 50% as in 0.01N H₃SO₃; I absorbs at much shorter wave lengths than III in EtOH, 0.1N NaOH, and 0.01N H₂SO₂; C₂H₂N₂ both have the same absorption in all solvents, very similar to that of II, and very different from that of V. It is concluded that all 3 matrine degradation compounds have the 4-aminopyridine skeleton, that I is 1-methyl-4,5,6,8,9,10-hexahydropyrido[3,4,5-ij]quinolizine, and that the C₁₂H₁₈N₂ are Me derivatives of 8-propyl-1,2,3,4-tetrahydro-1,6-naphthyridine.

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, Safety of 4-Amino-2-picoline.

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

Profft, Elmar published the artcilePreparation and pharmacological properties of 1-(4-alkoxy-2-pyridyl)-2-ethylpiperidines, SDS of cas: 18437-58-6, the publication is Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft (1958), 429-36, database is CAplus.

The title compounds in which the alkoxy group was MeO, EtO, PrO, BuO, iso-BuO, AmO, iso-AmO, n-C₆H₁₃O, or n-C₇H₁₅O were prepared and tested for their activity as local anesthetics by surface application of a 1% solution of their HCl salts. The PrO compound was prepared by treating 24 g. 2,4-Me(PrO)C₅H₃N with 12 g. 40% HCHO and 3 drops of HOAc at 190° for 8 h. and working up with Et₂O to give 7 g. 2,4-HOCH₂CH₂(PrO)C₅H₃N (I), yellow oil, b₁₈ 182-6°. I (10 g.) kept with 2 g. KOH for 40 h., some hydroquinone added, and the product vacuum distilled gave 2,4-CH₂:CH(PrO)C₅H₃N (II), b₂₀ 125-7°. II (0.05 mol) heated with 0.033 mol piperidine and 0.0043 mol HOAc for 3 h. on a water bath at 95-110°, then vacuum distilled gave 1-(4-propoxy-2-pyridyl)-2-ethylpiperidine, a golden oil, b₁₆ 200.5°. The other members of the series were prepared in a similar manner. Only the n-C₆H₁₃O and n-C₇H₁₅O analogs showed any significant pharmacol. activity as local anesthetics. Quaternary iodides were also prepared from the 4-alkoxy-2-methylpyridines where the alkoxy group was MeO, EtO, PrO, BuO, or AmO by treatment of 0.02 mol of the picoline with 0.021 mol MeI in 3-5 mL. EtOH for 3 h.

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 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, SDS of cas: 18437-58-6.

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

Suzuki, Yasuyuki published the artcileReactions of 4-pyridine- and 4-quinolinesulfonic acids with amines, Synthetic Route of 18437-58-6, the publication is Yakugaku Zasshi (1961), 1146-50, database is CAplus.

4-Pyridinesulfonic acid, 4-HO₃SC₅H₄N, (I) (1.6 g.) in 16 ml. 28% NH₄OH and a small amount of ZnCl₂ in an autoclave heated 2 hrs. at 150-60° cooled, 10 ml. 2N NaOH added, the NH₄OH removed and the product extracted with CHCl₃ gave 0.65 g. 4H₂NC₅H₄N, m. 157-8°. 2,4-Me(HO₃S)C₅H₃N (3 g.), 30 ml. 28% NH₄OH and a small amount ZnCl₂ in an autoclave heated 24 hrs. at 150-60° and the product treated as above gave 1.21 g. 2,4-Me(H₂N)C₅H₃N, m. 94-5°. Similarly prepared were the following amino compounds (product, % yield, and m.p. given): 3,4-Me(H₂N)C₅H₃N, 57.2, 107.5-9.0°; 2,6,4-Me₂(H₂N)C₅H₂N, 70.8, 192-3°; [from 4-HO₃SC₉H₆N (II)] 4-H₂NC₉H₆N, 79.5, 153°. I (1.6 g.), 10 ml. 33% MeNH₂ and a small amount of ZnCl₂ heated 24 hrs. at 130° gave 0.87 g. 4-MeNHC₅H₄N; picrate, m. 122-4°. Similarly, I and Me₂NH yielded 72.5% 4-Me₂NC₅H₄N, m. 112-13° (picrate, m. 204°); II and MeNH₂ yielded 88.3% 4-MeNHC₉H₆N, m. 224°; II and Me₂NH yielded 76.3% 4-Me₂NC₉H₆N, b₁₀ 167° (picrate, m. 192°). 2-HO₃SC₅H₄N (1.6 g.), 3.2 ml. 80% N₂H₄.H₂O, 7 ml. H₂O, and a small amount of ZnCl₂ in an autoclave heated 24 hrs. at 100-5°, the solution filtered, the filtrate concentrated in vacuo, the residue in 10 ml. 50% KOH extracted with Et₂O, and the picrate formed gave 2.1 g. 2-H₂NNHC₅H₄N picrate, m. 162-3° (decomposition). Similarly prepared were the following hydrazine derivatives (starting material, product, % yield and m.p. or m.p. of its salt given): I, 4-H₂NNHC₅H₄N (III), 72, HCl salt, 242-4°; 2-HO₃SC₉H₆N, 2-H₂NNHC₉H₆N, 64.5, picrate, 187-9° (decomposition); II, 4-H₂NNHC₉H₆N (IV), 81.2, HCl salt, 3078°; 2,4-Me(HO₃S)C₉H₅N, 2,4-Me(H₂NNH)C₉H₅N, 73.3, picrate, 206° (decomposition). 4-H₂NNHC₉H₆N.HCl (0.5 g.) in 10 ml. H₂O, 2 ml. EtOH and 1 ml. 10% NaOH, while refluxing, treated dropwise with 15 ml. 10% CuSO₄, refluxed 1 hr., refluxed 1 hr. with 5 ml. 10% NaOH and the product steam distilled gave 0.25 g. C₉H₇N; picrate, m. 202-3°. III.HCl (1 g.) in 50 ml. absolute EtOH treated with EtONa (0.16 g. Na and 7 ml. EtOH), the NaCl removed, the solution concentrated to 10 ml., refluxed 1 hr. with 0.8 g. Et pyruvate and the product concentrated gave 1.05 g. Et pyruvate 4-pyridylhydrazone, columns, m. 128-30°. III.HCl (1.45 g.) in 40 ml. MeOH treated with 1 g. KSCN in 10 ml. MeOH, refluxed 9 hrs. and the product concentrated gave 1.4 g. III.HSCN, m. 1079°. III (from 1.6 g. III.HCl) in 10 ml. C₅H₅N at 0° treated dropwise with 1.55 g. BzCl, stirred 1 hr. at room temperature, kept overnight, the solvent removed, and the residue washed with H₂O gave 1.2 g. 4-pyridyldibenzoylhydrazine, m. 2345° (EtOH). III (from 1.45 g. III.HCl) in 10 ml. EtOH and 1 g. AcCH₂COMe refluxed 1 hr., the EtOH removed, the residue in 5 ml. 10% NaOH and 10 ml. H₂O extracted with CHCl₃ and the product distilled gave 1.15 g. 1-(4-pyridyl)3,5-dimethylpyrazole, b₅ 131-4°; picrate m. 237° (decomposition). A solution of 1.26 g. AcONa.3H₂O, 3 ml. H₂O, 1 g. IV.HCl, 0.37 g. Me₂CO and 1 ml. AcOH refluxed 1.5 hrs., cooled, 4 ml. H₂O added and the mixture made alk. with NH₄OH and kept overnight at 0° gave 0.62 g. acetone 4-quinolylhydrazone, m. 122°. IV (0.5 g.) in 5 ml. EtOH and 0.34 g. PhCHO refluxed 1 hr. and the product concentrated gave 0.46 g. benzaldehyde 4-quinolylhydrazone, m. 11314°. IV.HCl (0.9 g.) in 20 ml. H₂O, 0.63 g. AcONa.3H₂O and 0.4 g. pyruvic acid mixed well and the product filtered off gave 0.73 g. pyruvic acid 4-quinolylhydrazone, m. 246° (decomposition). IV (0.35 g.) in 4 ml. EtOH and 0.25 g. Et pyruvate refluxed 1 hr. and the solution concentrated gave 0.31 g. Et pyruvate 4-quinolylhydrazone, m. 178°. IV.HCl (1.4 g.), 0.7 g. KSCN, and 50 ml. MeOH refluxed 12 hrs. and the solution concentrated gave 1.2 g. IV.HSCN, m. 168-9°. IV (0.5 g.) in 5 ml. C₅-H₅N and 0.44 g. BzCl refluxed 3 hrs. and the product concentrated gave 0.37 g. 1-(4-quinolyl)-2-(benzoyl)hydrazine, m. 129.5-30.5°. IV (0.66 g.) in 5 ml. EtOH and 0.42 g. AcCH₂COMe refluxed 1 hr., the EtOH removed and the residue in 10% NaOH extracted with CHCl₃ gave 0.66 g. 1-(4quinolyl)-3,5-dimethylpyrrazole, b₄ 180-1°; picrate m. 198° (MeOH).

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 C11H9ClN2O, Synthetic Route of 18437-58-6.

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

Li, Yan published the artcilePalladium-catalyzed cross-coupling of benzyltitanium(IV) reagents with aryl fluorides, Name: 4-Fluoropicolinonitrile, the publication is Monatshefte fuer Chemie (2022), 153(2), 193-199, database is CAplus.

The first palladium-catalyzed cross-coupling between benzyltitanium(IV) reagents with aryl fluorides is reported. A variety of diarylmethanes can be prepared in good to excellent yields by the catalyst system of PdCl₂(dppf)₂ associated with 1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxypiperidine. This reaction offered a highly efficient approach to diarylmethanes that are commonly found in life-changing drug mols.

Monatshefte fuer Chemie 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

Wolkenberg, Scott E. published the artcileDesign, synthesis, and evaluation of novel 3,6-diaryl-4-aminoalkoxyquinolines as selective agonists of somatostatin receptor subtype 2, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid, the publication is Journal of Medicinal Chemistry (2011), 54(7), 2351-2358, database is CAplus and MEDLINE.

Agonists of somatostatin receptor subtype 2 (sst₂) have been proposed as therapeutics for the treatment of proliferative diabetic retinopathy and exudative age-related macular degeneration. An HTS screen identified 2-quinolones as weak agonists of sst₂, and these were optimized to provide small mols. with sst₂ binding and functional potency comparable to peptide agonists. Agonist I was shown to inhibit rat growth hormone secretion following systemic administration and to inhibit ocular neovascular lesion formation after local administration.

Journal of Medicinal Chemistry published new progress about 903899-13-8. 903899-13-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Alcohol,Boronic Acids,Boronic acid and ester, name is (6-Hydroxypyridin-3-yl)boronic acid, and the molecular formula is C3H5BN2O2, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid.

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

Yuan, Chunling published the artcileCu(II)-catalyzed homocouplings of (hetero)arylboronic acids with the assistance of 2-O-methyl-D-glucopyranose, COA of Formula: C5H6BNO2, the publication is Molecules (2019), 24(20), 3678pp., database is CAplus and MEDLINE.

This is the first report of a natural ligand improving the copper-catalyzed homocouplings of (hetero)arylboronic acids. Various important synthetic biaryl intermediates in organic synthesis could be assembled via this method. To gain insight into this reaction, in-situ React IR technol. was used to confirm the effectivity of this catalyst system. This protocol provides important biaryl compounds in high yields within a short time.

Molecules 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 C6H16OSi, COA of Formula: C5H6BNO2.

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