Category: naphthyridine

Sousa, Ana Catarina published the artcileSynthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst, HPLC of Formula: 116-63-2, the publication is Advanced Synthesis & Catalysis (2020), 362(16), 3380-3387, database is CAplus.

An efficient and environmentally benign biocatalytic strategy for the synthesis of substituted 4-arylamino-1,2-naphthoquinones was developed, through a cross-coupling reaction in which the 1,2-naphthoquinone nucleus, formed in the biocatalytic process mediated by CotA-laccase from Bacillus subtilis, is the key synthetic intermediate. Electrochem. data and kinetic parameters were determined revealing a significant higher specificity of CotA-laccase for 4-amino-3-hydroxynaphthalene-1-sulfonic acid (AHNSA). This ability of CotA-laccase to discriminate between oxidisable aromatic amines allows the set-up of one-pot reactions in the presence of the enzyme, between AHNSA and a set of appropriate aromatic amines under mild reaction conditions.

Advanced Synthesis & Catalysis published new progress about 116-63-2. 116-63-2 belongs to naphthyridine, auxiliary class Sulfonic acid,Amine,Naphthalene,Alcohol,Organic Pigment, name is 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, and the molecular formula is C8H17Br, HPLC of Formula: 116-63-2.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Kang, Hyun Suk published the artcileConjugated-linker dependence of the photophysical properties and electronic structure of chlorin dyads, SDS of cas: 18512-55-5, the publication is Journal of Porphyrins and Phthalocyanines (2021), 25(7/8), 639-663, database is CAplus.

The synthesis, photophys. properties and electronic structure of seven new chlorin dyads and associated benchmark monomers are described. Each dyad contains two identical chlorins linked at the macrocycle β-pyrrole 13-position. The extent of electronic communication between chlorin constituents depends on the nature of the conjugated linker. The communication is assessed by modification of prominent ground-state absorption and redox properties, rate constants and yields of excited-state decay processes, and mol.-orbital characteristics. Relative to the benchmark monomers, the chlorin dyads in toluene exhibit a substantial bathochromic shift of the long-wavelength absorption band (30 nm average), two-fold increased radiative rate constant [average (10 ns)^-1 vs. (22 ns)^-1], reduced singlet excited-state lifetimes (average 5.0 ns vs. 8.2 ns), and increased fluorescence quantum yields (average 0.56 vs. 0.42). The excited-state lifetime and fluorescence yield for the chlorin dyad with a benzothiadiazole linker are reduced substantially in benzonitrile vs. toluene due largely to ∼ 25-fold accelerated internal conversion. The results aid design strategies for mol. architectures that may find utility in solar-energy conversion and photomedicine.

Journal of Porphyrins and Phthalocyanines published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, SDS of cas: 18512-55-5.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Morisaki, Yasuhiro published the artcileSynthesis of Anthracene-Stacked Oligomers and Polymer, Category: naphthyridine, the publication is Organic Letters (2010), 12(14), 3188-3191, database is CAplus and MEDLINE.

Anthracene-stacked oligomers and a polymer were synthesized using a xanthene skeleton as the scaffold, and their structures and properties were fully characterized. Intramol. π-π stacking of the anthracene rings in the ground state and excited state was observed

Organic Letters published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, Category: naphthyridine.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Ried, W. published the artcileEthynylation reactions. V. Aromatic diethynylhydrocarbons, SDS of cas: 18512-55-5, the publication is Angewandte Chemie (1958), 270, database is CAplus.

cf. preceding abstract 1,4-Diethynyl-1,4-dihydroxy-2,5-cyclohexadiene was reduced to 1,4-diethynylbenzene (I), m. 95°, and 9,10-diethynyl-9,10-dihydroxy-9,10-dihydroanthracene to 9,10-diethynylanthracene (II), yellow needles changing at 86-88° to a brown-black nonmelting substance. As reducing agents SnCl₂, Na dithionite, and TiCl₃ were used. I and II are fluorescent and light-sensitive. I + HCHO + Et₂NH gave a Mannich base, light yellow oil, b_0.4 108-10°; HCl salt, m. 187-8°.

Angewandte Chemie published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, SDS of cas: 18512-55-5.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Ried, Walter published the artcileEthynation reactions. IX. Aromatic diethynylhydrocarbons and the action of hydrogen halides on diethynyl-p-benzoquindiol, Recommanded Product: 9,10-Diethynylanthracene, the publication is Chemische Berichte (1958), 2472-9, database is CAplus.

Diethynylquindiols (I) are reduced by ZnCl₂ or HI to aromatic diethynylhydrocarhons which are light-sensitive; some of them show fluorescence. The reaction of diethynyl p-benzoquindiol (1,4-dihydroxy-1,4-diethynyl-2,5-cyclohexadiene) (II) with HI or HBr yields in addition to diethynylbenzene, several halogen-containing rearrangement products. p-Benzoquinone (40 g.) in 1 l. dry Et₂O added with stirring at -35 to -40° with stirring to LiCCH from 6 g. Li in 500 cc. liquid NH₃, the mixture neutralized after 5-8 hrs. with 60 g. solid NH₄Cl, the NH₃ evaporated, and filtered, the residue extracted with three 300-cc. portions EtOAc, and the combined filtrate and extract evaporated on the water bath yielded about 16 g. II, m. 192-5° (1:1:1 C₆H₆-ligroine-dioxane) (the diethynyl hydrocarbons frequently decompose explosively above 100°; their solutions are best evaporated on a water bath). II (16 g.) in solution added at 40-5° dropwise with stirring to 45 g. SnCl₂.2H₂O in 50 cc. 50% aqueous AcOH, stirred 10 min. at 45°, cooled, and filtered, and the residue washed with H₂O yielded 5.6 g. p-C₆H₄(CCH)₂ (III), yellowish leaflets, m. 95° (dilute EtOH or petr. ether); the original filtrate diluted with 2N HCl and extracted with Et₂O, and the extract worked up gave an addnl. 1.7 g. III. III (0.5 g.) in 20 cc. 90% AcOH refluxed 4 hrs. with 250 mg. Hg(OAc)₂ and 0.1 cc. concentrated H₂SO₄, cooled. treated with 40 cc. H₂O, and neutralized with aqueous Na₂CO₃, and the product isolated with Et₂O yielded 0.5 g. p-C₆H₄Ac₂, m. 108-10° (EtOH). 2,3,5,6-Tetrachloro-1,4-dihydroxy-1,4-diethynyl-2,5-cyclohexadiene (5 g.) in 25 cc. MeOH added with stirring at 70° to 10 g. SnCl₂.2H₂O in 20 cc. concentrated HCl, stirred 10 min. at 70°, cooled, and filtered, the residue washed with H₂O and dissolved in 70 cc. hot MeOH and filtered, and the boiling filtrate diluted with H₂O to turbidity and cooled gave 1 g. p-C₆Cl₄(CCH)₂, needles which turn brown above 100°, change the crystal form at 130-40°, and show no definite m.p. 1,4-Dihydroxy-1,4-diethynyl-1,4-dihydronaphthalene (4.2 g.) in 25 cc. EtOH added at 30-5° to 9 g. SnCl₂.2H₂O in 25 cc. 50% AcOH, stirred 10 min. at 30-5°, treated with 40 cc. 2N HCl, cooled in ice, and filtered, the residue washed with H₂O and dissolved in warm petr. ether, the solution evaporated, the residue dissolved at 50° in MeOH, and the solution treated with C, diluted hot with H₂O to turbidity, and cooled deposited 49% 1,4-C₁₀H₆(CCH)₂ (IV), yellowish, light-sensitive needles, m. 60°. Solid 2,3-dichloro-1,4-naphthoquinone (40 g.) and 100 cc. dry PhMe added with stirring at -40° to LiCCH from 3 g. Li in 300 cc. liquid NH₃, the mixture neutralized after 18 hrs. with 30 g. NH₄Cl, the NH₃ evaporated, the residue extracted with three 300-cc. portions boiling EtOAc, and the extract worked up yielded 2,3-dichloro-1,4-dihydroxy-1,4-diethynyl-1,4-dihydronaphthalene (V), prisms, m. 184-5° (1:1:1 C₆H₆-ligroine-dioxane, then dilute EtOH). V (5 g.) in 25 cc. MeOH added with stirring at 50° to 10 g. SnCl₂.2H₂O in 30 cc. 50% AcOH, heated 10 min. at 65°, cooled in ice, and filtered, and the crystalline residue recrystallized from ligroine, b. 70-90°, and then 80% EtOH yielded 1 g. 2,3-di-Cl derivative (VI) of IV, light-sensitive needles which turn rapidly violet (even in the dark), decompose 135° with flashing; after prolonged storage, the decomposition point had changed to 151°. V (1.5 g.) in 20 cc. MeOH refluxed 5 min. with 10 cc. 2N HI, cooled, and extracted with Et₂O, and the extract washed with aqueous Na₂S₂O₃ and evaporated yielded about 80% crude VI. VI hydrogenated over Raney Ni in EtOAc yielded 2,3,1,4-Cl₂C₁₀H₄Et₂, pale yellow prisms, m. 92-3° (Me₂CO). 9,10-Dihydroxy-9,10-diethynyl-9,10-dihydroanthracene (VII) (2.6 g.) in 25 cc. EtOH added with stirring at 5-10° to 5 g. SnCl₂.2H₂O in 50 cc. 50% AcOH and filtered after 10 min., the residue washed with H₂O and dissolved at 50 in 100-50 cc. Me₂CO, the solution filtered and diluted with H₂O precipitated 9,10-diethynylanthracene (VIII), yellow needles which turned golden-yellow in light and then black-brown, changed at 86-8° to a brown-black solid which did not melt up to 300°. VII (2.6 g.) in 25 cc. MeOH treated with stirring at 5-10° with 10 cc. 2N HI, stirred 10 min. with cooling, and filtered gave VIII. VIII hydrogenated over Raney Ni in EtOAc gave 9,10-diethylanthracene, yellow prisms, m. 145° (MeOH-Me₂CO). 9,10-Dihydroxy-9,10-diethynyl-9,10-dihydrophenanthrene (13 g.) in 100 cc. EtOH added at 60° with stirring to 22.5 g. SnCl₂.2H₂O in 45 cc. concentrated HCl and 30 cc. H₂O, the mixture kept 1 hr. at 60-5° and cooled to room temperature, and the precipitate dried on a clay plate, digested with 5-10 cc. CCl₄, and recrystallized from hot CCl₄ or C₆H₆ yielded 3 g. 9,10-diethynylphenanthrene, needles or leaflets, which turned brown above 100° and decompose spontaneously at 130°. 1,4-Dihydroxy-1,4-bis(phenylethynyl)-2,5-cyclohexadiene (2 g.) in 30 cc. MeOH added to 3 g. SnCl₂.2H₂O in 100 cc. 50% AcOH, stirred 1 hr. at room temperature and 2 hrs. at 50-60°, cooled, diluted with 200 cc. H₂O and 20 cc. concentrated HCl, and extracted with Et₂O, and the residue from the extract recrystallized from ligroine yielded 50-60% p-C₆H₄(CCPh)₂, m. 181-2°. 1,4-Dihydroxy-1,4-bis(3-methoxy-1-propynyl)-2,5-cyclohexadiene (IX) (50 g.) in MeOH added with stirring to 100 g. SnCl₂.2H₂O in 250 cc. 50% AcOH, stirred 2 hrs. at 60°, and filtered, the MeOH evaporated in vacuo, the residual mixture diluted with 700 cc. EtOAc and treated with about 100 g. CaCl₂, the EtOAc layer neutralized with NaHCO₃ and filtered, the residue washed with EtOAc, the combined filtrate dried and evaporated, the oily residue rubbed, the crystalline deposit filtered off, the viscous filtrate distilled under N, the distillate, b_0.7 145-55°, allowed to stand, the new crystalline deposit filtered off, and the combined filter residues digested with MeOH gave 70% (crude) p-(MeOCH₂CC)₂C₆H₄, m. 42-3° (cyclohexane); the MeOH filtrate worked up gave a small amount 2,4-(MeOCH₂CC)₂C₆H₃OH (X), m. 94° (ligroine). IX treated with warm 50% AcOH gave good yields of X. 9,10-Dihydroxy-9,10-bis(phenylethynyl)-9,10-dihydrophenanthrene (1 g.) in MeOH added to 3 g. SnCl₂.2H₂O in 100 cc. 50% AcOH, heated on the water bath, and filtered, and the residue recrystallized from ligroine yielded 80% 9,10-bis(phenylethynyl)phenanthrene, needles, m. 157° (MeOH). I (4 g.) in 30 cc. MeOH added dropwise to 130 cc. 7% HI, and heated 20 min. at 60-70°, the aqueous layer extracted with Et₂O, the combined organic layers evaporated, and the residual oil heated on the water bath at 12 mm. sublimed 10% p-C₆H₄(CCH)₂ and left 60-5% oily p-AcC₆H₄CCH; 2,4-dinitrophenylhydrazone, dark red, m. 210°. II (2 g.) in 40 cc. H₂O treated at 80° with 10 cc. 250% HI, kept 5 min. at 80°, cooled, and extracted with Et₂O, the extract washed with aqueous Na₂S₂O₃, dried, and evaporated, and the residue warmed with 20 cc. petr. ether, cooled, and filtered, and the filtrate evaporated gave p-CHCC₆H₄CI:CHI, pale yellow needles, m. 74-5° (80% EtOH). II (5 g.) in 70 cc. MeOH added dropwise with stirring to 150 cc. 7% HBr, stirred 10 min. at room temperature and 0.5 hr. at 60-70°, the aqueous layer extracted with Et₂O, and the combined organic layers worked up gave 50-60% p-CHCC₆H₄COCH₂Br (XI), needles, m. 46-8° (aqueous MeOH); 2,4-dinitrophenylhydrazone, yellow crystals, decompose 180-90°. XI (1 g.) in 10 cc. MeOH refluxed 2 hrs. with 30 cc. 10% aqueous KCN and distilled, and the residue acidified yielded 100% p-CHCC₆H₄COCH₂CN, m. 184°; 2,4-dinitrophenylhydrazone, orange-yellow about 160°. II (3.2 g.) and 40 cc. 25% HBr heated 5 min. with stirring at 80°, the precipitated oil extracted into Et₂O, the solution washed and evaporated, and the residue heated with 90% aqueous MeOH and C and filtered yielded 1.7 g. p-CHCC₆H₄CBr: CHBr, pale yellow needles, m. 64-5°.

Chemische Berichte published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, Recommanded Product: 9,10-Diethynylanthracene.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Turcas, Crina Valentina published the artcileAzo dye complexes. Synthesis and tinctorial properties, COA of Formula: C10H9NO4S, the publication is Scientific Bulletin – University “Politehnica” of Bucharest, Series B: Chemistry and Materials Science (2012), 74(1), 109-118, database is CAplus.

Exptl. results concerning synthesis of copper, cobalt, and chromium complex combinations with azo dyes starting from 1-diazo-2-naphthol-4-sulfonic acid and 6-nitro-1-diazo-2-naphthol-4-sulfonic acid by coupling with β-naphthol or 4-(diethylamino)-2-naphthol are presented. These complex combinations were characterized by elemental chem. anal. and electronic and IR spectra. Their dyeing properties on wool and polyamide were determined

Scientific Bulletin – University “Politehnica” of Bucharest, Series B: Chemistry and Materials Science published new progress about 116-63-2. 116-63-2 belongs to naphthyridine, auxiliary class Sulfonic acid,Amine,Naphthalene,Alcohol,Organic Pigment, name is 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, and the molecular formula is C11H12O4, COA of Formula: C10H9NO4S.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Quidville, Virginie published the artcile15-Hydroxyprostaglandin-dehydrogenase is involved in anti-proliferative effect of non-steroidal anti-inflammatory drugs COX-1 inhibitors on a human medullary thyroid carcinoma cell line, Recommanded Product: Sulindac sulfone, the publication is Prostaglandins & Other Lipid Mediators (2006), 81(1-2), 14-30, database is CAplus and MEDLINE.

Non-steroidal anti-inflammatory drugs (NSAIDs) inhibit prostaglandin (PG) synthesis enzymes, the cyclooxygenases (COX-1 and 2). It is suggested that these enzymes are not their only targets. We reported that in tumoral TT cell, indomethacin, in vivo and in vitro, decreases proliferation and increases activity of 15-hydroxyprostaglandin-dehydrogenase (15-PGDH), the PG catabolism key enzyme. Here, we show that the COX-1 inhibitors, selective or not, and sulindac sulfone, a non-COX inhibitor, increased 15-PGDH activity and reduced PGE₂ levels. This increase was neg. correlated to the decrease in cell proliferation and suggested that 15-PGDH could be implicated in NSAIDs anti-proliferative effect. Indeed, the silencing of 15-PGDH expression by RNA interference using 15-PGDH specific siRNA enhanced TT cell proliferation and abolished the anti-proliferative effect of a representative non-selective inhibitor, ibuprofen. Moreover, a specific inhibitor of 15-PGDH activity, CAY 10397, completely reversed the effect of ibuprofen on proliferation. Consequently our results demonstrate that, at least in TT cells, 15-PGDH is implicated in proliferation and could be a target for COX-1 inhibitors specific or not. NSAIDs defined by their COX inhibition should also be defined by their effect on 15-PGDH.

Prostaglandins & Other Lipid Mediators published new progress about 59973-80-7. 59973-80-7 belongs to naphthyridine, auxiliary class Immunology/Inflammation,COX, name is Sulindac sulfone, and the molecular formula is C20H17FO4S, Recommanded Product: Sulindac sulfone.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Teli, M. D. published the artcileAntibacterial textiles using antibacterial dyes, Synthetic Route of 116-63-2, the publication is Asian Dyer (2011), 8(4), 37-40, database is CAplus.

The application of zinc complex dyes on silk and nylon for obtaining a more permanent way of microbial protection to textiles was explored. In order to do so, the preparation and characterization of 2:1 zinc complexes were performed. The 2:1 zinc metal complex dyes were successfully synthesized. These premetallized zinc complex dyes were found to exhibit excellent antibacterial properties. As long as these dyes are on the fabric, its antibacterial property continues to last, offering a new route of obtaining durable antibacterial properties on silk and nylon fabrics.

Asian Dyer published new progress about 116-63-2. 116-63-2 belongs to naphthyridine, auxiliary class Sulfonic acid,Amine,Naphthalene,Alcohol,Organic Pigment, name is 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, and the molecular formula is C16H21N3O3S, Synthetic Route of 116-63-2.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Tathe, Abhinav B. published the artcileNovel Fluorescent Phenazines : Synthesis, Characterization, Photophysical Properties and DFT Calculations, Quality Control of 116-63-2, the publication is Journal of Fluorescence (2015), 25(5), 1403-1415, database is CAplus and MEDLINE.

The organic compounds with donor-π-bridge-acceptor type of architecture are of great interest for application as semiconductors. The synthesized compounds are obtained from 4-morpholino naphthalene-1,2-dione and 4-(4-(diethylamino) phenyl)naphthalene-1,2-dione and mono substituted ortho-phenylene diamines by condensation reaction. The donor groups are morpholinyl and N,N-diethylamino Ph moieties, whereas acceptors are substituted phenazines. The synthesized mols. were characterized by spectral anal.. The effect of the substitution has been studied on the basis of photophys. properties of the mols. The halochromism behavior of the mol. shows that at low to moderate acidity they respond differently with two types of donors. DFT computations were used in conjunction with NMR anal. to determine the ratio of the positional isomers.

Journal of Fluorescence published new progress about 116-63-2. 116-63-2 belongs to naphthyridine, auxiliary class Sulfonic acid,Amine,Naphthalene,Alcohol,Organic Pigment, name is 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, and the molecular formula is C6H8O6, Quality Control of 116-63-2.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Aikawa, Kohsuke published the artcilePalladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with (Difluoromethyl)zinc Reagent, Recommanded Product: 1-(Difluoromethyl)naphthalene, the publication is Organic Letters (2016), 18(15), 3690-3693, database is CAplus and MEDLINE.

The palladium-catalyzed Negishi cross-coupling reaction of aryl iodides I [R = CN-4, NO₂-4, CO₂Et-4, Cl-4, (Bu-t)-4, OMe-4, Ph-4, Me₂-3,5, CHOCHCHOCH-2,3, Me₃-2,4,6; X = I] and bromides I [R = NO₂-4, CO₂Et-4, (Bu-t)-4, CN-3; X = Br] with (difluoromethyl)zinc reagent bearing a diamine such as TMEDA is achieved to provide the difluoromethylated aromatic compounds II in good to excellent yields. The advantages of (difluoromethyl)zinc reagent are that (1) the derivatives, which possess different stability and reactivity, can be readily prepared via ligand screening and (2) transmetalation of a difluoromethyl group from the zinc reagent to palladium catalyst efficiently proceeds without an activator.

Organic Letters published new progress about 53731-26-3. 53731-26-3 belongs to naphthyridine, auxiliary class Difluoromethyl,Fluoride,Naphthalene, name is 1-(Difluoromethyl)naphthalene, and the molecular formula is C11H8F2, Recommanded Product: 1-(Difluoromethyl)naphthalene.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem