Category: naphthyridine

Payagala, Tharanga published the artcileSynthesis and chromatographic evaluation of new polymeric chiral stationary phases based on three (1S,2S)-(-)-1,2-diphenylethylenediamine derivatives in HPLC and SFC, HPLC of Formula: 2960-93-2, the publication is Analytical and Bioanalytical Chemistry (2011), 399(7), 2445-2461, database is CAplus and MEDLINE.

Three new polymeric chiral stationary phases were synthesized based on (1S,2S)-1,2-bis(2,4,6-trimethylphenyl)ethylenediamine, (1S,2S)-1,2-bis(2-chlorophenyl)ethylenediamine, and (1S,2S)-1,2-di-1-naphthylethylenediamine via a simple free-radical-initiated polymerization in solution These monomers are structurally related to (1S,2S)-1,2-diphenylethylenediamine which is the chiral monomer used for the com. P-CAP-DP polymeric chiral stationary phase (CSP). The performance of these three new chiral stationary phases were evaluated in normal phase HPLC and supercritical fluid chromatog. and the results were compared with those of the P-CAP-DP column. All three new phases showed enantioselectivity for a large number of racemates with a variety of functional groups, including amines, amides, alcs., amino acids, esters, imines, thiols, and sulfoxides. In normal phase, 68 compounds were separated with 28 baseline separations (Rs �1.5) and in SFC, 65 compounds were separated with 24 baseline separations In total 72 out of 100 racemates were separated by these CSPs with 37 baseline separations Complimentary separation capabilities were observed for many analytes. The new polymeric CSPs showed similar or better enantioselectivities compared with the com. column in both HPLC and SFC. However, faster separations were achieved on the new stationary phases. Also, these polymeric stationary phases have good sample loading capacities while maintaining enantioselectivity.

Analytical and Bioanalytical Chemistry published new progress about 2960-93-2. 2960-93-2 belongs to naphthyridine, auxiliary class Naphthalene,Ether,Other MOF ligands,Organic ligands for MOF materials, name is 2,2′-Dimethoxy-1,1′-binaphthalene, and the molecular formula is C22H18O2, HPLC of Formula: 2960-93-2.

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

Fuchibe, Kohei published the artcileSynthesis of (difluoromethyl)naphthalenes using the ring construction strategy: C-C bond formation on the central carbon of 1,1-difluoroallenes via Pd-catalyzed insertion, Application In Synthesis of 53731-26-3, the publication is Organic & Biomolecular Chemistry (2019), 17(20), 5047-5054, database is CAplus and MEDLINE.

The insertion of 1,1-difluoroallenes was carried out to form a C-C bond exclusively on their central carbon. O-Bromophenyl-bearing 1,1-difluoroallenes underwent intramol. insertion in the presence of a palladium catalyst. Regioselective C-C bond formation occurred to form a six-membered carbocycle, leading to pharmaceutically and agrochem. promising difluoromethylated naphthalenes.

Organic & Biomolecular Chemistry 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, Application In Synthesis of 53731-26-3.

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

Jackson, S. David published the artcileAdsorption of chiral 2,2′-substituted-1,1′-binaphthalenes onto silica-supported palladium and nickel, Formula: C22H18O2, the publication is Adsorption Science & Technology (2006), 24(3), 257-267, database is CAplus.

The nature of the adsorption of 2,2′-substituted-1,1′-binaphthalenes over supported palladium and nickel catalysts were studied. Adsorption occurs through the 2,2′-substituted functional groups. Where this is not possible, no adsorption of the binaphthyl is observed Adsorption of 2,2′-diamino-1,1′-binaphthalene occurred solely on the metal components of the catalysts. However, total coverage of the metal surface was not obtained, with only specific sites being available for adsorption. Adsorption of 2,2′-dihydroxy-1,1′-binaphthalene occurred on the metal components but also spilled over onto the support. Adsorption was detected for 2-hydroxy-2′-methoxy-1,1′-binaphthalene but no spill-over was observed, indicating that both hydroxy groups are involved in the spill-over process. Co-adsorption and sequential adsorption studies revealed that there are a variety of adsorption sites that favor different binaphthyls.

Adsorption Science & Technology published new progress about 2960-93-2. 2960-93-2 belongs to naphthyridine, auxiliary class Naphthalene,Ether,Other MOF ligands,Organic ligands for MOF materials, name is 2,2′-Dimethoxy-1,1′-binaphthalene, and the molecular formula is C22H18O2, Formula: C22H18O2.

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

Gilman, Henry published the artcileOxygen-containing heterocycles as liquid scintillator solutes, Recommanded Product: Spiro[fluorene-9,9′-xanthene], the publication is Journal of Organic Chemistry (1958), 361-2, database is CAplus.

cf. C.A. 52, 5424h. Derivatives of dibenzofuran (I), dibenzo-p-dioxin (II) and xanthene were screened as liquid scintillator solutes and the primary-solute relative pulse heights relative to 2,5-diphenyloxazole (arbitrary value 1.00) are tabulated. The biphenyl linkage in I presumably makes all its derivatives superior to corresponding II derivatives The results suggest that the introduction of MeO and dialkylamino groups increases the relative pulse height by shortening the lifetime of the excited state and providing a greater probability that fluorescence will occur before a radiationless transition (C.A. 52, 5382d). The values tabulated indicated that further work on II is promising only with 2-substituted derivatives Cu bronze (4 g.) and 4.0 g. 1-iododibenzo-p-dioxin heated 5 hrs. at 250° (oil bath), the cooled pulverized mixture extracted with hot C₆H₆ and the concentrated extract diluted with alc. yielded 22% 1,1′-bis(dibenzo-p-dioxin), m. 217-19°. Cu bronze (5 g.) and 4.0 g. 2-iododibenzo-p-dioxin heated 4 hrs. at 240-50°, the cooled pulverized mixture extracted with hot C₆H₆, the extract chromatographed on Al₂O₃, the eluate diluted with alc. and the product recrystallized (AcOH) yielded 22% 2,2′-bis(dibenso-p-dioxin), m. 227-30°. Nitrous fumes slowly bubbled 2.5 hrs. through 4.0 g. 2-acetamidodibenzo-p-dioxin in 130 ml. AcOH and 20 ml. Ac₂O at 10°, the yellow-green solution poured into 1 l. ice-H₂O, the air-dried solid stirred 8 hrs. in 200 ml. dry C₆H₆ and kept 8 hrs. at room temperature, warmed 1 hr. and the C₆C₆ evaporated, the concentrated solution chromatographed on Al₂O₃ and the fraction recrystallized (alc.) gave 16% 2-phenyldibenzo-p-dioxin, m. 108-10°, with characteristic 1,2,4-tri-, 1,2-di-, and monosubstitution bands in the infrared spectrum. Excess PhCH₂MgCl added in 15 min. with stirring and gentle refluxing to 5.76 g. 2-benzoyldibenzo-p-dioxin in 100 ml. Et₂O, the mixture refluxed 2 hrs., hydrolyzed with saturated aqueous NH₄Cl, the dried (Na₂SO₄) Et₂O layer evaporated and the residue crystallized (alc.-H₂O) 3 times yielded 60% 1-(2-dibenzo-p-dioxinyl)-1,2-diphenylethanol (III), m. 141-2°. III (3.5 g.) and 15 ml. Lucas reagent (cf. Crawford and Nelson, C.A. 40, 1484⁸) refluxed 2 hrs. in 45 ml. C₆H₆, the washed (dilute aqueous Na₂CO₃) C₆H₆ layer evaporated, the oily residue boiled with ligroine (b. 60-70°) and the solid product crystallized (alc.-H₂O) 3 times yielded 33% 2-(α-phenylstyryl)dibenzo-p-dioxin. The use of Lucas reagent renders isolation of III unnecessary since dehydration was effected conveniently using crude carbinol solutions in C₆H₆.

Journal of Organic Chemistry published new progress about 159-62-6. 159-62-6 belongs to naphthyridine, auxiliary class Other Aromatic Heterocyclic,Spiro, name is Spiro[fluorene-9,9′-xanthene], and the molecular formula is C25H16O, Recommanded Product: Spiro[fluorene-9,9′-xanthene].

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

Allani, S. K. published the artcileSulindac induces differentiation of glioblastoma stem cells making them more sensitive to oxidative stress, Category: naphthyridine, the publication is Neoplasma (2018), 65(3), 376-388, database is CAplus and MEDLINE.

Glioblastoma tumors (GBM) are very heterogeneous, being comprised of several cell subtypes, including glioblastoma stem cells (GSC). These tumors have a high rate of recurrence after initial treatment and one of the most prevalent theories to explain this is the cancer stem cell theory, which proposes that glioblastomas arise from mutations that transform normal neural stem cells (NSC) into GSC, which are highly resistant to oxidative stress and anti-cancer therapies. To study the effect of sulindac on both normal and cancer stem cells, we have isolated normal neural stem cells (NSC), from mice hippocampi and glioblastoma stem cells (GSC) from a glioma cell line, U87. As expected from previous studies sulindac can protect normal astrocytes against oxidative stress. Sulindac induces differentiation of both NSC and GSC cells and sulindac upregulates neurogenesis in NSC. The differentiated NSC are also protected from oxidative stress damage, whereas the differentiation of GSC by sulindac increases the sensitivity of these cells to agents that cause oxidative stress. The S epimer of sulindac is more effective than the R epimer in inducing neuronal differentiation in both NSC and GSC. These results indicate that the ability of sulindac to induce GSC differentiation may have therapeutic value in preventing tumor recurrence.

Neoplasma 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, Category: naphthyridine.

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

Kung, Hsiu-Ni published the artcileSulindac compounds facilitate the cytotoxicity of β-lapachone by up-regulation of NAD(P)H quinone oxidoreductase in human lung cancer cells, Product Details of C20H17FO4S, the publication is PLoS One (2014), 9(2), e88122/1-e88122/15, 15 pp., database is CAplus and MEDLINE.

β-Lapachone, a major component in an ethanol extract of Tabebuia avellanedae bark, is a promising potential therapeutic drug for various tumors, including lung cancer, the leading cause of cancer-related deaths worldwide. In the first part of this study, we found that apoptotic cell death induced in lung cancer cells by high concentrations of β-lapachone was mediated by increased activation of the pro-apoptotic factor JNK and decreased activation of the cell survival/proliferation factors PI3K, AKT, and ERK. In addition, β-lapachone toxicity was pos. correlated with the expression and activity of NAD(P)H quinone oxidoreductase 1 (NQO1) in the tumor cells. In the second part, we found that the FDA-approved non-steroidal anti-inflammatory drug sulindac and its metabolites, sulindac sulfide and sulindac sulfone, increased NQO1 expression and activity in the lung adenocarcinoma cell lines CL1-1 and CL1-5, which have lower NQO1 levels and lower sensitivity to β-lapachone treatment than the A549 cell lines, and that inhibition of NQO1 by either dicoumarol treatment or NQO1 siRNA knockdown inhibited this sulindac-induced increase in β-lapachone cytotoxicity. In conclusion, sulindac and its metabolites synergistically increase the anticancer effects of β-lapachone primarily by increasing NQO1 activity and expression, and these two drugs may provide a novel combination therapy for lung cancers.

PLoS One 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, Product Details of C20H17FO4S.

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

Ried, Walter published the artcileEthynylation reactions. XV. Light reactions of 1,4-diethynyl aromatic compounds, Application In Synthesis of 18512-55-5, the publication is Journal fuer Praktische Chemie (Leipzig) (1961), 306-9, database is CAplus.

cf. CA 55, 13392d, 21068c. Light sensitivity of diethynyl aromatic compounds (I) (CA 53, 5210f) was used in preparation of offset printing plates. I, coated from solution onto Al plates, was exposed to light through a negative, unreacted I was removed with solvents, and exposed Al etched with 1% H₃PO₄. Light sensitivity of I increased in the order: 1,4-diethynyl benzene, 9,10-diethynyl anthracene, 1,4-diethynyl naphthalene, and 1,4-diethynyl-2,3-dichloronaphthalene. Light caused ethynyl groups to trimerize to polymeric benzene derivatives

Journal fuer Praktische Chemie (Leipzig) 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, Application In Synthesis of 18512-55-5.

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

Kim, Kenneth P. published the artcileCombinatorial chemoprevention: Efficacy of lovostatin and exisulind on the formation and progression of aberrant crypt foci, Application In Synthesis of 59973-80-7, the publication is Anticancer Research (2004), 24(3A), 1805-1811, database is CAplus.

Background: There are several advantages to combinatorial chemoprevention strategies over monotherapeutic approaches. Both the HMG-CoA reductase inhibitor (HRI) lovastatin (LOV) and the selective apoptotic antineoplastic drug (SAAND) exisulind (EXS) have shown remarkable chemopreventive effects in previous studies, in cell lines and limited studies in rodents. Here, experiments were designed to assess the potential use of these two compounds in combinatorial chemoprevention therapy, using two bio-assays in which inhibition of the carcinogen-induced preneoplastic lesions, aberrant crypt foci (ACF), was used to quantitate efficacy. Materials and Methods: ACF were induced by the carcinogen azoxymethane (AOM) in F344 rats by two sequential weekly i.p. injections at a dose of 15 mg/kg. F344 rats were fed seven exptl. diets containing LOV @ 50 ppm (ppm), EXS @ 100, 250 and 1000 ppm and combination diets containing EXS at 100, 250 and 1000 ppm, each combined with LOV @ 50 ppm. Quantification of ACF number and type (singlet, doublet, triplet and four or more) was performed on whole mounts of rat colons stained with 1.0% methylene blue. Results: During the initiation protocol, administration of LOV @ 50 ppm alone and the combination of LOV @ 50 ppm with EXS @ 1000 ppm significantly decreased the mean number of ACF when compared to the pos. control by 49% and 47%, resp.; however EXS @ 250 ppm displayed tumor promoting effects by significantly increasing the mean number of ACF by 64%. The post-initiation protocol administration of EXS @ 100, 250 and 1000 ppm and the combinations of LOV @ 50 ppm with EXS @ 100 and 250 ppm significantly increased the mean number of ACF when compared to the pos. control by 44%, 48%, 55%, 49% and 40%, resp. Conclusion: LOV shows greater promise than EXS in fulfilling the role as a supplemental chemopreventive agent in combinatorial chemopreventive strategies for cancers such as colon cancer. EXS did not augment this activity, failing to enhance chemopreventive therapy in this animal model.

Anticancer Research 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, Application In Synthesis of 59973-80-7.

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

Salter, E. A. published the artcileHomology models of the catalytic sites of phosphodiesterase 5A and 10A and molecular docking of selective apoptotic antineoplastic drugs (SAANDs), Formula: C20H17FO4S, the publication is International Journal of Quantum Chemistry (2004), 96(4), 402-410, database is CAplus.

Achieving selective inhibition for individual gene families of cyclic nucleotide phosphodiesterases (CNPDE) isoenzymes has become an important pharmacol. goal now that the diversity of these hydrolases has been recognized. Selective apoptotic antineoplastic drugs (SAANDs) induce apoptosis in neoplastic cells and not in normal cells by a mechanism involving inhibition of overexpressed PDEs that hydrolyze cyclic GMP. SAANDs, although not selective, show a preference for PDE5 and PDE10. However, highly selective PDE5 inhibitors do not induce apoptosis. To study differences in PDE inhibitors, we constructed homol. models of the target catalytic domains of PDE5A and PDE10A based upon the X-ray crystal structure of the catalytic domain of PDE4B. Mol. mechanics docking is planned to define new SAANDs vs. ineffective agents. We investigated the binding of exisulind (Aptosyn) and other analogs to PDE4, 5, and 10 isoforms using our mol. models and compared the resultant estimated binding energies with exptl. IC₅₀ values. Proposed binding orientations for CP 248, a higher-affinity and more selective inhibitor of PDE5 and PDE10 than exisulind, are presented. The modeling studies described here allowed us to identify some differing structural features of the catalytic pockets that may be helpful in the development of active and more selective drugs to treat tumors found in different tissues while maintaining minimal side effects.

International Journal of Quantum Chemistry 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, Formula: C20H17FO4S.

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

Sheng, Huaming published the artcileIdentification of the sulfoxide functionality in protonated analytes via ion/molecule reactions in linear quadrupole ion trap mass spectrometry, Recommanded Product: Sulindac sulfone, the publication is Analyst (Cambridge, United Kingdom) (2014), 139(17), 4296-4302, database is CAplus and MEDLINE.

A mass spectrometric method using gas-phase ion/mol. reactions of 2-methoxypropene (MOP) has been developed for the identification of the sulfoxide functionality in protonated analytes in a LQIT mass spectrometer. Protonated sulfoxide analytes react with MOP to yield an abundant addition product (corresponding to 37-99% of the product ions), which is accompanied by a much slower proton transfer. The total efficiency (percent of gas-phase collisions leading to products) of the reaction is moderate (3-14%). A variety of compounds with different functional groups, including sulfone, hydroxylamino, N-oxide, aniline, phenol, keto, ester, amino and hydroxy, were examined to probe the selectivity of this reaction. Most of the protonated compounds with proton affinities lower than that of MOP react mainly via proton transfer to MOP. The formation of adduct-MeOH ions is characteristic for secondary N-hydroxylamines. N-Oxides formed abundant MOP adducts just like sulfoxides, but sulfoxides can be differentiated from N-oxides based on their high reaction efficiencies. The reaction was tested by using the antiinflammatory drug sulindac (a sulfoxide) and its metabolite sulindac sulfone. The presence of a sulfoxide functionality in the drug but a sulfone functionality in the metabolite was readily demonstrated. The presence of other functionalities in addition to sulfoxide in the analytes was found not to influence the diagnostic reactivity.

Analyst (Cambridge, United Kingdom) 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 C8H11NO, Recommanded Product: Sulindac sulfone.

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