Category: 1569-17-1

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called 1,8-Naphthyridines. I. Derivatives of 2- and 4-methyl-1,8-naphthyridines, published in 1965, which mentions a compound: 1569-17-1, Name is 4-Methyl-1,8-naphthyridine, Molecular C9H8N2, Synthetic Route of C9H8N2.

2-Methyl-1,8-naphthyridine has been prepared by a series of reactions starting with 2-methyl-5-hydroxy-1,8-naphthyridine-6-carboxylic acid and compared with the known 4-methyl-1,8-naphthyridine. The compound previously thought to be 2-methyl-4-hydroxy-7-amino-l,8-naphthyridine has been shown to be 2-hydroxy-4-methyl-7-amino-1,8-naphthyridine by conversion to 4-methyl-1,8-naphthyridine. A new ring closure has furnished 2-methyl-7-amino-1,8-naphthyridine and, in addition, 2-amino-5-methyl-1,8-naphthyridine and 2-methyl-5-amino-1,8-naphthyridine have been prepared by other means.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Yakugaku Zasshi called Catalytic dehalogenation reaction, Author is Miyaki, Takaaki; Kataoka, Eisei, which mentions a compound: 1569-17-1, SMILESS is CC1=C2C=CC=NC2=NC=C1, Molecular C9H8N2, Recommanded Product: 4-Methyl-1,8-naphthyridine.

Catalytic dehalogenation of 2,7-dichloro-4-methyl-1,8-naphthyridine with Pd-CaCO3 gave 4-methylnaphthyridine and chloro-4-methylnaphthyridine (the details to be reported later). Catalytic dehalogenation of 2,4-dichloro-6-methylpyrimidine gave a compound whose picrate (m. 130-1°) did not depress the m. p. of 6-methylpyrimidine picrate. In like manner the following compounds were studied with the reaction indicated: 4-phenyl-2,6-dichloropyrimidine → C10H8N2, m. 66-7°; 1-bromo-β-naphthol → β-naphthol; 1-bromo-β-naphthol Me ether → β-naphthol Me ether; bromopiperonal → piperonal; o-BrC6H4NO2 → aniline + o-bromoaniline + 2,2′-dibromoazoxybenzene.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Yakugaku Zasshi called Catalytic dehalogenation reaction, Author is Miyaki, Takaaki; Kataoka, Eisei, which mentions a compound: 1569-17-1, SMILESS is CC1=C2C=CC=NC2=NC=C1, Molecular C9H8N2, Recommanded Product: 1569-17-1.

Catalytic dehalogenation of 2,7-dichloro-4-methyl-1,8-naphthyridine with Pd-CaCO3 gave 4-methylnaphthyridine and chloro-4-methylnaphthyridine (the details to be reported later). Catalytic dehalogenation of 2,4-dichloro-6-methylpyrimidine gave a compound whose picrate (m. 130-1°) did not depress the m. p. of 6-methylpyrimidine picrate. In like manner the following compounds were studied with the reaction indicated: 4-phenyl-2,6-dichloropyrimidine → C10H8N2, m. 66-7°; 1-bromo-β-naphthol → β-naphthol; 1-bromo-β-naphthol Me ether → β-naphthol Me ether; bromopiperonal → piperonal; o-BrC6H4NO2 → aniline + o-bromoaniline + 2,2′-dibromoazoxybenzene.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 1569-17-1, is researched, SMILESS is CC1=C2C=CC=NC2=NC=C1, Molecular C9H8N2Journal, Chemical & Pharmaceutical Bulletin called Syntheses of nitrogen-containing compounds. XVII. Improvement of one-step synthesis of naphthyridine derivatives and their methylation with demethyl sulfoxide in the presence of base, Author is Hamada, Yoshiki; Takeuchi, Isao; Hirota, Minoru, the main research direction is naphthyridine methylation MD calculation.Application In Synthesis of 4-Methyl-1,8-naphthyridine.

1,8-Naphthyridines were synthesized in a high yield by the reaction of 2-aminopyridines with glycerol, in the presence of Na m-nitrobenzenesulfonate, in H2SO4. Methylation of naphthyridines with Me2SO in the presence of NaH or KOBu-tert afforded their mono-Me or di-Me compounds This methylation with methylsulfinyl carbanion was examined from the Hueckel MO method; the calculation agreed with the exptl. results.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Kinetics of quaternization of some naphthyridines and methylnaphthyridines.Product Details of 1569-17-1.

The 2nd order rate constants for the reaction of MeI with some naphthyridines and methylnaphthridines in MeCN were determined by a conductimetric method. The following results were obtained at 24.8° (compound, and rate constant × 10-4 l./mole/sec. given): quinoline, 0.517; isoquinoline, 4.23; 1,5-naphthyridine, 0.232; 1,6-naphthyridine, 1.66; 1,8-naphthyridine, 4.25; 2-methyl-1,8-naphthyridine, 3.61; 3-methyl-1,8-naphthyridine, 5.74; 4-methyl-1,8-naphthyridine, 7.26; and 2,7-dimethyl-1,8-naphthyridine, 1.85. The rate constants are used to deduce the quaternization kinetics of the reactions.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of 1,8-naphthyridine homologs and their hydrogenation》. Authors are Ochiai, Eiji; Miyaki, Komei.The article about the compound:4-Methyl-1,8-naphthyridinecas:1569-17-1,SMILESS:CC1=C2C=CC=NC2=NC=C1).Electric Literature of C9H8N2. Through the article, more information about this compound (cas:1569-17-1) is conveyed.

In earlier work (CA 33:2525.5) it was found that Me 1,4-dihydroxy-2,5-naphthyridine-3-carboxylate (C. A. numbering, 5,8-dihydroxy-1,6-naphthyridine-7-carboxylate) and the 1-Cl compound on catalytic hydrogenation take up H only on the nonsubstituted pyridine ring. In continuation of this work, 2,4-dimethyl- (I) and 4-methyl-1,8-naphthyridine (II) have been synthesized and a similar phenomenon on hydrogenation has been observed. In the meantime some other 1,8-naphthyridines described in this paper have been prepared by analogous methods by Mangini (preceding abstract). 7-Amino derivative of I (0.5 g. from 2 g. 2,6-diaminopyridine, 2 g. CH2Ac2 and 1 g. fused ZnCl2 heated 3 hrs. at 120-30°), m. 220° (Ac derivative, pale yellow, m. 300°), converted by diazotization in 40% H2SO4 into the 7-HO compound, m. 251°, which, heated 30 min. in a sealed tube at 140° with POCl3, gives the 7-Cl compound, m. 146-7°; this, boiled 30 min. with 20% MeONa in MeOH, gives the 7-MeO compound, m. 65° (picrate, m. 188-9°). Hydrogenation of 1 g. of the HO compound in 20 g. alc. with 1 g. Ni-kieselguhr under 110 atm. of H for 10 hrs. at 170-80° gave, along with 0.6 g. unchanged material, 0.2 g. of a dihydro derivative, C10H12N2O, m. 175-80°. The Cl compound (0.5 g.), shaken in 10% KOH-MeOH with 0.2 g. of 20% Pd-charcoal and H until about 1.2 mols. H had been absorbed, and the product chromatographed in benzene through Al2O3, yielded about 0.05 g. I, m. 85-6° (HCl salt, decomposes 240°; picrate, decomposes 204-6°; methiodide, yellow needles with 1 H2O, m. 93-4; chloroplatinate, I.H2PtCl6, decomposes 242-4°; chloroaurate, decomposes 166-7°). When 0.1 g. of the Cl compound in 10 cc. of 10% KOH-MeOH was hydrogenated to saturation with 0.5 g. of 20% Pd-charcoal it yielded the tetrahydro derivative (III) of I described below. With 1.2 g. of the Cl compound in 20 cc. of 5% KOH-MeOH, 0.5 g. PdO-CaCO3 and a trace of Pd-charcoal, the hydrogenation stopped in 30 min. (about 170 cc. H absorbed) and 0.8 g. I was obtained. Shaken in 10 cc. AcOH with 0.1 g. Pt oxide and H to saturation, 0.5 g. I absorbed about 160 cc. H and yielded 0.5 g. of a tetrahydro derivative (III), m. 118°, giving a pos. Liebermann reaction (picrate, m. 207°; Ac derivative, m. 42-3°); III was also obtained in 0.85-g. yield from 1 g. I in 50 cc. cyclohexane and 5 cc. alc. with 1 g. Raney Ni heated under an initial H pressure of 70 atm. 2 hrs. at 120° and 2 hrs. at 190°. III was unchanged by 4 hrs. treatment in AcOH with Pt oxide and 110 atm. H pressure, at room temperature With Na in boiling alc., however, it yielded the decahydro derivative of I, easily subliming needles, m. 92-3° (di-Ac derivative, thick oil, b0.02 135-45°). 2,7-Dichloro-4-methyl-1,8-naphthyridine in 10% KOH-MeOH hydrogenated with PdO-CaCO3 and a trace of Pd-charcoal gave, together with a mono-Cl compound, C9H7ClN2, m. 104°, chiefly (about 70%) II, b0.05 147-8° (picrate, decomposes 204-5°; perchlorate, m. 180-1°). II (1 g.) in 10 cc. AcOH with 0.5 g. Pt oxide and H yielded a mixture of 2 isomeric tetrahydro derivatives, separated by fractional crystallization from petr. ether: 0.2 g. of a more soluble isomer A (IV), m. 62-3°, giving a pos. Liebermann reaction (Bz derivative, m. 86-7°), and about 0.8 g. of a less soluble isomer B (V), m. 102-3° (picrate, decomposes 248°; Bz derivative, m. 105-6°; nitro derivative, m. 217-18° and giving a pos. Liebermann reaction, prepared by treating the tetrahydride in cold H2SO4 (dry ice-acetone) with fuming HNO3 (d.1.6), pouring on ice, crystallizing from alc., heating the crystals (m. 124-5°) in concentrated H2SO4 at 60°, again pouring on ice, filtering, making alk. with Na2HPO4 and extracting with ether). V is unchanged by hydrogenation in AcOH with PtO and 65 atm. H pressure. With Na in boiling AmOH, both isomers yield the same (racemic) decahydro derivative of II, b0.1 70-80°, m. 87°, gives a pos. Liebermann reaction (picrate, decomposes 210°). The structures of III, IV and V have not been definitely established but the following considerations make it highly probable what they are. The work of earlier investigators on the hydrogenation of quinoline homologs with Ni and H under pressure and with Sn and HCl has shown that Me groups have a disturbing influence on the hydrogenation of the ring half on which they are substituted whereas Na and alc. readily hydrogenate the Me-substituted rings. This disturbing effect of Me groups is ascribed to the inductive effect of the Me group. III is considered to be the 5,6,7,8-tetrahydro compound To further confirm this, III was heated in a little alc. with an excess of ClCH2COMe for 4 hrs. at 100°; the resulting addition product, C15H21ClN22O2, m. 181-2°, allowed to stand 1 day in a little water with 2 drops of 10% Na3CO3, gave, in addition to unchanged III, a resin whose blue Ehrlich reaction pointed to the presence of an indolizine ring. Such a ring can be formed only from a nonhydrogenated 2-methylpyridine. IV is considered to be the 1,2,3,4- and V the 5,6,7,8-tetrahydro compound because the latter is formed in the larger amount; its higher m. p. is also in harmony with such an assumption.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

HPLC of Formula: 1569-17-1. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Spectral data of substituted naphthyridines. V. The IR spectra of substituted 1,8-naphthyridines. Author is Wozniak, Marian; Roszkiewicz, Witold.

In general the IR spectra of 1,8-naphthyridines show a ring bending (skeletal) vibration at 690-740-cm-1, three adjacent H absorption at 750-795 and 810-885 cm-1, two adjacent H absorptions at 785-855 cm-1 and isolated H absorptions at 795-810 and 885-920 cm-1.

From this literature《Spectral data of substituted naphthyridines. V. The IR spectra of substituted 1,8-naphthyridines》,we know some information about this compound(1569-17-1)HPLC of Formula: 1569-17-1, but this is not all information, there are many literatures related to this compound(1569-17-1).

Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Spectral data of substituted naphthyridines. V. The IR spectra of substituted 1,8-naphthyridines, published in 1979, which mentions a compound: 1569-17-1, mainly applied to IR naphthyridine derivative, Category: naphthyridine.

In general the IR spectra of 1,8-naphthyridines show a ring bending (skeletal) vibration at 690-740-cm-1, three adjacent H absorption at 750-795 and 810-885 cm-1, two adjacent H absorptions at 785-855 cm-1 and isolated H absorptions at 795-810 and 885-920 cm-1.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Identification of 1,5-Naphthyridine Derivatives as a Novel Series of Potent and Selective TGF-β Type I Receptor Inhibitors, published in 2004-08-26, which mentions a compound: 1569-17-1, mainly applied to aminothiazole naphthyridine preparation transforming growth factor receptor inhibitor; aminopyrazole naphthyridine preparation transforming growth factor receptor inhibitor; naphthyridinylaminothiazole preparation transforming growth factor alk5 autophosphorylation inhibitor; naphthyridine preparation transforming growth factor inhibitor structure activity relationship, Product Details of 1569-17-1.

Optimization of the screening hit I led to the identification of novel 1,5-naphthyridine aminothiazole and pyrazole derivatives, which are potent and selective inhibitors of the transforming growth factor-β type I receptor, ALK5. Compounds II and III, which inhibited ALK5 autophosphorylation with IC50 = 6 and 4 nM, resp., showed potent activities in both binding and cellular assays and exhibited selectivity over p38 mitogen-activated protein kinase. The X-ray crystal structure of III in complex with human ALK5 is described, confirming the binding mode proposed from docking studies.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Magee, Thomas V.; Ripp, Sharon L.; Li, Bryan; Buzon, Richard A.; Chupak, Lou; Dougherty, Thomas J.; Finegan, Steven M.; Girard, Dennis; Hagen, Anne E.; Falcone, Michael J.; Farley, Kathleen A.; Granskog, Karl; Hardink, Joel R.; Huband, Michael D.; Kamicker, Barbara J.; Kaneko, Takushi; Knickerbocker, Michael J.; Liras, Jennifer L.; Marra, Andrea; Medina, Ivy; Nguyen, Thuy-Trinh; Noe, Mark C.; Obach, R. Scott; O’Donnell, John P.; Penzien, Joseph B.; Reilly, Usa Datta; Schafer, John R.; Shen, Yue; Stone, Gregory G.; Strelevitz, Timothy J.; Sun, Jianmin; Tait-Kamradt, Amelia; Vaz, Alfin D. N.; Whipple, David A.; Widlicka, Daniel W.; Wishka, Donn G.; Wolkowski, Joanna P.; Flanagan, Mark E. published an article about the compound: 4-Methyl-1,8-naphthyridine( cas:1569-17-1,SMILESS:CC1=C2C=CC=NC2=NC=C1 ).Quality Control of 4-Methyl-1,8-naphthyridine. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:1569-17-1) through the article.

Respiratory tract bacterial strains are becoming increasingly resistant to currently marketed macrolide antibiotics. The current alternative telithromycin (1) from the newer ketolide class of macrolides addresses resistance but is hampered by serious safety concerns, hepatotoxicity in particular. We have discovered a novel series of azetidinyl ketolides that focus on mitigation of hepatotoxicity by minimizing hepatic turnover and time-dependent inactivation of CYP3A isoforms in the liver without compromising the potency and efficacy of 1.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem