Day: December 9, 2022

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

Surov, O. V. published the artcileEnthalpies of Fusion, sublimation and vaporization of some hydrazones, Quality Control of 2215-33-0, the publication is Physical Chemistry: An Indian Journal (2017), 12(1), 1-15, database is CAplus.

Enthalpies of melting, sublimation and vaporization were determined for some hydrazones. The validity of thermogravimetric procedure for measuring enthalpy of vaporization of the compounds under investigation was demonstrated. Exploring packing modes and intermol. interactions in mol. crystals of the hydrazones using Hirshfeld surfaces was carried out.

Physical Chemistry: An Indian Journal published new progress about 2215-33-0. 2215-33-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, and the molecular formula is C5H10Cl3O3P, Quality Control of 2215-33-0.

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

Shibata, Katsumi published the artcileNiacin activity of 3-cyanopyridine, pyridine 3-sulfonic acid, nicotinic acid N-oxide, and 6-hydroxynicotinic acid in rats, Application In Synthesis of 636-73-7, the publication is Bitamin (1995), 69(7), 357-64, database is CAplus.

Niacin activity of the niacin related compounds such as 3-cyanopyridine, pyridine 3-sulfonic acid, nicotinic acid N-oxide, and 6-hydroxynicotinic acid was investigated using rats. 3-Cyanopyridine, pyridine-3-sulfonic acid, and 6-hydroxynicotinic acid had not only niacin activity but also the antagonistic activity. Nicotinic acid N-oxide had niacin activity and the relative niacin activity to nicotinic acid was about 1/2 in molar ratio.

Bitamin published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C14H10O4S2, Application In Synthesis of 636-73-7.

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

Saielli, Giacomo published the artcileOne-bond ¹J(¹⁵N-¹⁹F) spin-spin coupling constants of cationic fluorinating reagents: Insights from DFT calculations, Product Details of C6H5F4NO3S, the publication is Magnetic Resonance in Chemistry (2020), 58(6), 548-558, database is CAplus and MEDLINE.

We have investigated, by means of d. functional theory protocols, the one-bond ¹J(¹⁵N-¹⁹F) spin-spin coupling constants in a series of fluorinating reagents, containing the N-F bond, recently studied exptl. The results of the calculations show a very good linear relationship with the exptl. values, even though only the M06-2X(PCM)/pcJ-2//B3LYP/6-311G(d,p) level affords a very low mean absolute error. The calculations allow to analyze the various MOs contributions to the J coupling and to rationalize the observed pos. sign, corresponding to a neg. sign of the reduced spin-pin coupling constant K(N-F). Moreover, of the four Ramsey contributions, only the diamagnetic spin orbit is negligible, whereas the paramagnetic spin orbit and spin dipole terms decrease the magnitude of the Fermi contact (FC) term by an amount that goes from a min. of 35% up to more than 60% of the FC term itself. Several effects have been investigated, namely, the contribution of the long-range solvent reaction field, relativistic corrections, and conformational and vibrational effects.

Magnetic Resonance in Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Product Details of C6H5F4NO3S.

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

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

Namekawa, Keisuke published the artcileMarine paint development trend and forecast. Environmental regulation related to the antifouling paints for the ship bottom and the corresponding antifouling agents, Formula: C23H20BN, the publication is Toso Gijutsu (2006), 45(8), 63-66, database is CAplus.

A review. The regulation for the ship bottom fouling prevention agents in Europe, the biocide product directive, the control of the antifouling agents for the paints for the ship bottom in Japan, the selection of the effective components of the antifouling agents, the toxicity of the antifouling agents for the ship bottom, and the examples of the degradability and accumulation properties of Zinc Omadine (zinc pyrithione), Copper Omadine (copper pyrithione), and Borocide P (triphenylboronpyridine) are reviewed.

Toso Gijutsu published new progress about 971-66-4. 971-66-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is Triphenyl(pyridin-1-ium-1-yl)borate, and the molecular formula is C23H20BN, Formula: C23H20BN.

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

Mihkelson, A. E. published the artcileReactions of palladium(II) with a series of potentially tridentate nitrogen ligands. II. Solution studies, Application In Synthesis of 2215-33-0, the publication is Journal of Inorganic and Nuclear Chemistry (1981), 43(1), 127-36, database is CAplus.

Potentiometric and conductometric titrations of Pd²⁺ and pyridine-2-carboxaldehyde 2′-pyridylhydrazone (HL) in aqueous solution showed that only 1 mol of L coordinates with each Pd in solution There was no evidence for PdL₂ formation in aqueous solution Equilibrium constants were estimated for a model system using Job’s method of continuous variations. Proton NMR of PdL₂ and PdL¹OAc (HL¹ = 6-methylpyridine-2-carboxaldehyde 2′-pyridylhydrazone) showed that the ligand undergoes isomerization about the imine bond.

Journal of Inorganic and Nuclear Chemistry published new progress about 2215-33-0. 2215-33-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, and the molecular formula is C11H10N4, Application In Synthesis of 2215-33-0.

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

Melo, Eduardo Borges de published the artcileA structure-activity relationship study of the toxicity of ionic liquids using an adapted Ferreira-Kiralj hydrophobicity parameter, Related Products of pyridine-derivatives, the publication is Physical Chemistry Chemical Physics (2015), 17(6), 4516-4523, database is CAplus and MEDLINE.

The Ferreira-Kiralj hydrophobicity parameter W_c is a number fraction of hydrophobic carbon atoms and can be regarded as a constitutional descriptor since its calculation depends only on the number of polar and nonpolar carbons in a compound Hydrophobicity is important to the toxicity of ionic liquids (ILs), which are salts by nature. Herein, a descriptor for this property was calculated using a simple adaptation of the type of polar carbon atoms included (W_cAdap) to explore the possibility of its use in quant. structure-activity relationship (QSAR) studies of ILs. The resulting model was tested using a database of ILs with toxicity against the Leukemia rat cell line IPC-81. Two other models were constructed using Crippen log P and Mannhold log P descriptors, which are both available in the free program PaDEL. The use of W_cAdap led to a better and more indicative model. Thus, W_cAdap may be a suitable mol. descriptor for the hydrophobicity of ILs in QSAR studies.

Physical Chemistry Chemical Physics 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, Related Products of pyridine-derivatives.

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

Lombardini, John B. published the artcileQuantitative analysis of the combination dose-effects of taurine and taurine analogs on the phosphorylation of an ∼44-Kd protein present in a mitochondrial subfraction of rat heart, COA of Formula: C5H5NO3S, the publication is Journal of Cardiovascular Pharmacology (1996), 28(1), 107-114, database is CAplus and MEDLINE.

Combinations of taurine and analogs of taurine that partially contain the N-C-C-S moiety within a semirigid saturated ring structure were tested for their effects on the phosphorylation of an ∼44-Kd protein present in the mitochondrial fraction of rat heart. (±)-Piperidine-3-sulfonic acid (PiP), an inhibitor of the phosphorylation of the ∼44-Kd protein with activity approx. similar to that of taurine, was observed to be mutually exclusive with taurine, i.e., to have a similar mode of action. The combination of taurine plus PiP in a fixed ratio mixture of 1:1 was slightly antagonistic at all concentrations (±)-Aminotetrahydrothiopyran-1,1-dioxide (APS), a sulfone derivative of taurine with a net pos. charge, also has approx. the same inhibitory activity as taurine. However, APS was mutually nonexclusive with taurine when tested in combination and thus appears to act independently of taurine. Taurine plus APS in a fixed ratio mixture of 3:1 was highly antagonistic at low concentrations of the mixture, approached an additive relation at 50% saturation, and became synergistic at high concentrations of the mixture Three analogs of taurine, pyridine-3-sulfonic acid (PyS), quinoline-8-sulfonic acid (QS), and 2-aminobenzenesulfonic acid (ABS), that have the basic taurine structure (N-C-C-S) partially in a semirigid unsaturated ring structure stimulate the phosphorylation of the ∼44-Kd protein. Due to the unsaturated ring structure, these analogs of taurine have a net neg. charge at physiol. pH and are not zwitterions. When PyS, QS, or ABS was titrated in the presence of a fixed concentration of taurine (10 mM), there was a competitive relation even through their electronic nature is quite different than that of taurine. The combination of QS plus PyS (1:5) appears to progress through a transition from being synergistic at low concentrations of the fixed ratio mixture, additive at 50% saturation, and finally antagonistic at high concentration of the fixed ratio mixture

Journal of Cardiovascular Pharmacology published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C5H5NO3S, COA of Formula: C5H5NO3S.

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