Heterocyclic Building Blocks-Naphthyridine

Sancho, Raquel published the artcilePolyproline derivatives as chiral selectors in high performance liquid chromatography: Chromatographic and conformational studies, Formula: C22H18O2, the publication is Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences (2008), 875(1), 93-101, database is CAplus and MEDLINE.

A proline oligopeptide-derived chiral selector (CS), containing 3,5-dimethylphenylcarbamate residues on the 4 position of the pyrrolidine rings, was bonded to a silica gel chromatog. matrix by the N-terminal group. The chromatog. behavior of the resulting chiral stationary phase (CSP) was compared with that of a CSP containing the analogous monomeric CS and that resulting from bonding of the polyproline-derived CS by the carboxy-terminal group using several solvents as mobile phase. The CSs were also studied from the conformational point of view in solution using CD and ¹³C NMR. A relation was found between the presence of an ordered conformation in the particular conditions used and increased enantioselectivity.

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 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

Novell, Arnau published the artcileOctaproline, a conformationally flexible chiral selector in liquid chromatographic enantioseparation, Safety of 2,2′-Dimethoxy-1,1′-binaphthalene, the publication is Journal of Chromatography A (2014), 109-118, database is CAplus and MEDLINE.

A proline octapeptide-derived chiral selector (CS) end-capped using a pivaloyl group was covalently linked to a silica gel chromatog. matrix by the C-terminal group. The chromatog. behavior of the resulting chiral stationary phase (CSP) using different conditions was compared to those containing 3,5-dimethylphenylcarbamate residues on the proline units. An enantioseparation ability highly dependent on the mobile phase used is observed for these CSPs. When mixtures of alkane/alc. or alkane/ether were used as mobile phase a similar enantioselectivity was obtained. Nevertheless, in the presence of chlorinated solvents, and without a hydrogen bonding donor in the mobile phase, enantioselectivity is extremely reduced. The reversibility of this phenomenon, attributed to a conformational change in the CS, was examined

Journal of Chromatography A 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, Safety of 2,2′-Dimethoxy-1,1′-binaphthalene.

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

Novell, A. published the artcileMonolithic silica columns with covalently attached octaproline chiral selector. Dependence of performance on derivatization degree and comparison with a bead-based analogue, Synthetic Route of 2960-93-2, the publication is Journal of Chromatography A (2015), 124-132, database is CAplus and MEDLINE.

A monolithic silica gel chromatog. matrix was derivatized repetitively with an octaproline-derived chiral selector (CS). The increasingly derivatized column was tested after each derivatization reaction. The enantioseparation ability, resolution and efficiency were found to depend on the content of CS attained after each reaction. Moreover, enantioselectivity and performance of the column with the highest CS coverage were compared to those of a bead-based chiral stationary phase (CSP) counterpart. The octaproline-derivatized monolithic column demonstrated increased enantioseparation factors, resolution and broader applicability than the particle-based column. Finally, the loading capacity of the CSPs was also examined The monolithic octaproline-derived column permits the separation of 3-20 times higher molar amounts of the tested analytes (depending on the compound considered) than the particle-based counterpart. The enhanced capabilities of the derivatized monolithic column with respect to that of a bead-based counterpart cannot be explained only on the basis of an increased CS coverage. The involvement of an effect produced by the chromatog. silica support structure in the obtained results is discussed.

Journal of Chromatography A 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, Synthetic Route of 2960-93-2.

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

Feng, Zhang published the artcileAccess to Difluoromethylated Arenes by Pd-Catalyzed Reaction of Arylboronic Acids with Bromodifluoroacetate, Recommanded Product: 1-(Difluoromethyl)naphthalene, the publication is Organic Letters (2016), 18(1), 44-47, database is CAplus and MEDLINE.

An unprecedented example of Pd-catalyzed difluoromethylation of aryl boronic acids with bromodifluoroacetate is described. The reaction proceeds under mild reaction conditions with hydroquinone and Fe(acac)₃ as additives. Preliminary mechanistic studies reveal that a difluorocarbene pathway is involved in the reaction, which is unusual compared to the most traditional approaches. This reaction has advantages of high efficiency and excellent functional group compatibility, even toward bromide and hydroxy group, thus providing a useful protocol for drug discovery and development.

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

Feng, Zhang published the artcileChlorodifluoromethane-triggered formation of difluoromethylated arenes catalysed by palladium, Product Details of C11H8F2, the publication is Nature Chemistry (2017), 9(9), 918-923, database is CAplus and MEDLINE.

Difluoromethylated aromatic compounds are of increasing importance in pharmaceuticals, agrochems. and materials. Chlorodifluoromethane (ClCF₂H), an inexpensive, abundant and widely used industrial raw material, represents the ideal and most straightforward difluoromethylating reagent, but introduction of the difluoromethyl group (CF₂H) from ClCF₂H into aromatics has not been reported. Here, we describe a direct palladium-catalyzed difluoromethylation method for coupling ClCF₂H with arylboronic acids and esters to generate difluoromethylated arenes with high efficiency. The reaction exhibits a remarkably broad substrate scope, including heteroarylboronic acids, and was used for difluoromethylation of a range of pharmaceuticals and biol. active compounds Preliminary mechanistic studies revealed that a palladium difluorocarbene intermediate is involved in the reaction. Although numerous metal-difluorocarbene complexes were prepared, the catalytic synthesis of difluoromethylated or difluoromethylenated compounds involving metal-difluorocarbene complexes has not received much attention. This new reaction therefore also opens the door to understand metal-difluorocarbene complex catalyzed reactions.

Nature 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, Product Details of C11H8F2.

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

Xu, Ling published the artcileDiastereo- and enantioselective syntheses of ansa-metallocenes from metal halide complexes with tropos biphenol and atropos binaphthol ethers, Category: naphthyridine, the publication is Tetrahedron Letters (2004), 45(50), 9215-9217, database is CAplus.

A diastereo- and enantioselective route to synthesize ethylene-bis(4,5,6,7-tetrahydro-1-indenyl)-titanium and -zirconium dichlorides is described using titanium trichloride or zirconium tetrachloride complexes with tropos (chirally flexible) biphenol and atropos (chirally rigid) binaphthol ethers.

Tetrahedron Letters 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 C15H14O, Category: naphthyridine.

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

Motohashi, Hirotaka published the artcileNickel-Catalyzed Aromatic Cross-Coupling Difluoromethylation of Grignard Reagents with Difluoroiodomethane, Quality Control of 53731-26-3, the publication is Organic Letters (2018), 20(17), 5340-5343, database is CAplus and MEDLINE.

The nickel-catalyzed cross-coupling difluoromethylation of the Grignard reagents with difluoroiodomethane is shown to provide the corresponding aromatic difluoromethyl products in excellent to moderate yields. The difluoromethylation proceeds smoothly within 1 h at room temperature with 1.5 equiv of the Grignard reagents in the presence of Ni(cod)₂/TMEDA (2.5-0.5 mol %). Mechanistic studies clarify that the oxidative addition of the Ni(0) catalyst to difluoroiodomethane provides the TMEDA-Ni(II)(CF₂H)I complex. This intermediate is transformed to TMEDA-Ni(II)(CF₂H)Ph via transmetalation with PhMgBr. The reductive elimination takes place to give the aromatic cross-coupling difluoromethylation product along with regeneration of the TMEDA-Ni(0) catalyst. ESR (EPR) and radical clock analyses of the nickel-catalyzed reaction provide no EPR active Ni(I) and Ni(III) species at around g = 2 and only a trace amount of the cyclization product.

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, Quality Control of 53731-26-3.

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

Bock, Jonathan M. published the artcileRelative non-steroidal anti-inflammatory drug (NSAID) antiproliferative activity is mediated through p21-induced G1 arrest and E2F inhibition, Category: naphthyridine, the publication is Molecular Carcinogenesis (2007), 46(10), 857-864, database is CAplus and MEDLINE.

This study was performed to compare the relative antineoplastic activity of 10 different non-steroidal anti-inflammatory drugs (NSAIDs) in clin. use, and to investigate the underlying mechanisms of this activity in a squamous cell carcinoma of the head and neck model (SCCHN). A standard 5-day MTT assay was used to calculate IC₅₀ values in UM-SCC-1 cells for 10 NSAIDs, including celecoxib, rofecoxib, sulindac sulfide, sulindac sulfone, indomethacin, ketoprofen, flurbiprofen, naproxen, piroxicam, and aspirin. Celecoxib, a COX-2 specific inhibitor, was by far the most potent NSAID, with an IC₅₀ of 39.9±1.1 μM, followed by sulindac sulfide (116.5±2.34 μM). Celecoxib and sulindac sulfide also induced more activation of caspase-3 than any other NSAID. Cell cycle anal. showed that celecoxib and sulindac sulfide both induced a 3-fold increase in G₁ phase distribution, and this correlated with strong induction of p21^waf1/cip1, inhibition of cyclin D1, and hypophosphorylation of Rb. Celecoxib and sulindac sulfide treatment induced strong downstream inhibition of E2F transactivating activity as determined by a luciferase reporter assay. These data demonstrate the wide range of activity of various NSAID agents, and reveal a mechanism of action through cell cycle inhibition and induction of apoptosis.

Molecular Carcinogenesis 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

Bock, Jonathan M. published the artcileDifferential activity of sulindac metabolites against squamous cell carcinoma of the head and neck is mediated by p21^waf1/cip1 induction and cell cycle inhibition, Quality Control of 59973-80-7, the publication is Cancer Biology & Therapy (2007), 6(1), 30-39, database is CAplus and MEDLINE.

Sulindac sulfide and sulindac sulfone have demonstrated anti-neoplastic and chemopreventive activity against various human tumors, but few studies have examined the relative effectiveness of these drugs against squamous cell carcinoma of the head and neck (SCCHN). These compounds are metabolites of the nonsteroidal anti-inflammatory drug sulindac and differ in their ability to inhibit cyclooxygenase-2 (COX-2) enzyme function. Sulindac sulfide (the sulindac metabolite with COX-2 inhibitory function) demonstrated strong cell growth inhibition as measured by MTT and growth assays in UM-SCC-1 and SCC-25 cells, while sulindac sulfone had only moderate effect. Growth inhibition by sulindac sulfide was associated with a significant increase in percent G₁ cells and activation of caspase-3. Sulindac sulfide induced expression of p21^waf1/cip1 in a dose-dependent fashion, decreased cyclin D1 protein levels, and increased Rb hypophosphorylation. P21^waf1/cip1 protein levels increased without a significant increase in wild-type p53, suggesting that sulindac sulfide induces a p53-independent pathway regulating p21^waf1/cip1 protein levels in SCCHN. Sulindac sulfide also induced dose-dependent expression of PPAR-γ. In contrast, sulindac sulfone did not significantly alter apoptosis, cell cycle distribution or G₁ checkpoint protein expression at doses below 200 μM. These results demonstrate the differential activity of sulindac metabolites and support the hypothesis that sulindac sulfide induced perturbations in SCCHN cellular proliferation could be regulated both by p21^waf1/cip1-dependent cytostatic and caspase-dependent cytotoxic pathways.

Cancer Biology & Therapy 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, Quality Control of 59973-80-7.

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

Gao, Lei published the artcileDevelopment and validation of a six-RNA binding proteins prognostic signature and candidate drugs for prostate cancer, COA of Formula: C20H17FO4S, the publication is Genomics (2020), 112(6), 4980-4992, database is CAplus and MEDLINE.

The dysregulation of RNA binding proteins (RBPs) regulates the progression of several cancers. However, information on the overall functions of RBPs in prostate cancer (PCa) remains largely understudied. Therefore, based on the TCGA dataset, this study identified 144 differentially expressed RBPs in tumors compared to normal tissues. Subsequently, through univariate, LASSO and multivariate Cox regression anal., 6 RBP genes among them, MSI1, MBNL2, LENG9, REXO2, RNASE1, and PABPC1L were screened as prognostic hub genes and prognostic signature was further identified. Further anal. indicated that the high-risk group was significantly associated with poor RFS, which was validated in the MSKCC cohort. Besides, patients in the high-risk group were closely associated with dysregulation of DNA damage repair pathway, copy number alteration, tumor burden mutation, and low-response to cisplatin (P lt 0.001), and bicalutamide (P lt 0.001). Using the Connectivity Map, we finally predicted 3 drugs including, ribavirin, carmustine, and carbenoxolone. In summary, we identified six-RBP gene signature and 3 potential drugs against PCa, which might promote the individualized treatment strategies and further improve the quality of life among PCa patients.

Genomics 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, COA of Formula: C20H17FO4S.

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