Category: naphthyridine

Yoshida, Masato published the artcileConvenient preparation of difluoromethylene-functionalized compounds from chlorodifluoroacetic acid, Safety of 1-(Difluoromethyl)naphthalene, the publication is Journal of Fluorine Chemistry (1994), 68(1), 33-8, database is CAplus.

A convenient route for the synthesis of difluoromethylene-functionalized compounds from chlorodifluoroacetic acid has been investigated. Bis(chlorodifluoroacetyl) peroxide, which was synthesized from chlorodifluoroacetic acid via its acid anhydride, was found to be a good reagent for the chlorodifluoromethylation of electron-rich aromatic compounds and olefins. The chlorine atom of the chlorodifluoromethylated compounds, thus prepared, exchanged hydrogen and allyl groups by reaction with tributyltin hydride and allyltributyltin, resp., under radical conditions.

Journal of Fluorine 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 C8H11NO, Safety of 1-(Difluoromethyl)naphthalene.

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

Yoshida, Masato published the artcileConvenient preparation of (chlorodifluoromethyl)arenes. Useful precursors for aryldifluoromethyl radicals, Safety of 1-(Difluoromethyl)naphthalene, the publication is Chemistry Letters (1992), 227-30, database is CAplus.

The chlorodifluoromethyl group was introduced into aromatic rings (of e.g., C₆H₆ to give PhCF₂Cl) using bis(chlorodifluoroacetyl) peroxide which was readily prepared from the corresponding acid anhydride with 30% hydrogen peroxide, and the chlorine was successively replaced by hydrogen or the allyl group in excellent yields under radical conditions.

Chemistry 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 C18H17N5O3, Safety of 1-(Difluoromethyl)naphthalene.

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

Massah, Ahmad R. published the artcileSolvent-free Williamson synthesis. An efficient, simple, and convenient method for chemoselective etherification of phenols and bisphenols, Related Products of naphthyridine, the publication is Synthetic Communications (2007), 37(11), 1807-1815, database is CAplus.

Etherification of phenols with dimethyl- and diethylsulfates and benzyl chloride was performed efficiently in the presence of a suitable solid base, NaHCO₃ or K₂CO₃, under solvent-free conditions. The reaction proceeded rapidly at low temperature, and the corresponding ethers were obtained with high purity and excellent yield. Selective etherification of electron-poor phenols in the presence of electron-rich ones and also selective mono-etherification of bisphenols are the noteworthy advantages of this method. This method is environmentally friendly.

Synthetic Communications 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, Related Products of naphthyridine.

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

Shirin, Haim published the artcileNon-steroidal anti-inflammatory drugs have bacteriostatic and bactericidal activity against Helicobacter pylori, Category: naphthyridine, the publication is Journal of Gastroenterology and Hepatology (2006), 21(9), 1388-1393, database is CAplus and MEDLINE.

Helicobacter pylori infection and non-steroidal anti-inflammatory drugs (NSAIDs) are each associated with gastrointestinal mucosal damage, but the extent and direction of their interactions remain controversial. Therefore, the purpose of the present paper was to examine whether specific NSAIDs inhibit the growth of Helicobacter pylori in vitro. Sodium salicylate, ibuprofen, indomethacin, the selective cyclooxygenase-2 inhibitor NS-398 and two derivatives of sulindac sulfoxide were tested against two laboratory strains of H. pylori, the mouse-adapted Sydney strain, and against seven fresh clin. isolates of Helicobacter pylori. Possible effects on Campylobacter jejuni, Staphyloccoccus aureus, Escherichia coli, Salmonella typhimurium, and Shigella boydii were also examined Certain NSAIDs possess antibacterial activity against Helicobacter pylori at therapeutically achievable doses; an effect that appears to be independent of cyclooxygenase enzymes inhibition. For Helicobacter pylori, >90% growth inhibition and bactericidal activity were observed consistently for sulindac sulfide at â‰?0 μg/mL and sulindac sulfone at â‰?75 μg/mL. The minimal inhibitory concentration against Helicobacter pylori was 125 μg/mL for ibuprofen, 100 μg/mL for indomethacin and 300 μg/mL for NS-398 but much higher concentration of sodium salicylate (4000 μg/mL) and sulindac sulfoxide (â‰?250 μg/mL) were required to inhibit the growth of Helicobacter pylori. The decreased prevalence of Helicobacter pylori in specimens from some NSAID users and the chemopreventive effects of NSAIDs in gastric cancer may be related to inhibition of Helicobacter pylori growth.

Journal of Gastroenterology and Hepatology 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 C4H6O3, Category: naphthyridine.

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

Hori, Kaishi published the artcilePrecatalyst Effects on Pd-Catalyzed Cross-Coupling Difluoromethylation of Aryl Boronic Acids, Category: naphthyridine, the publication is ACS Catalysis (2019), 9(1), 417-421, database is CAplus.

The Pd-catalyzed difluoromethylation of aryl boronic acids with difluoroiodomethane is shown to provide the difluoromethyl compounds I (R = H, 4-Ph, 3-MeO, 2-NH₂, etc.) in high to moderate yields by Pd(PPh₃)₂/DPEphos catalyst in H₂O/toluene. Mechanistic studies show that the oxidative addition by Pd(PPh₃)₄ rather than Pd₂(dba)₃ precatalyst to difluoroiodomethane provides a square-planar trans-(PPh₃)₂Pd(II)(CF₂H)I complex defined by X-ray crystallog. anal. The trans-(PPh₃)₂Pd(CF₂H)I complex is transformed to cis-(PPh₃)₂Pd(CF₂H)Ph detected by low temperature NMR anal., via transmetalation with phenylboronic acids. The reductive elimination occurs via ligand exchange to DPEphosPd(CF₂H)Ph to give Ph-CF₂H (t_1/2 = 144.7 min at 20 °C) with formation of the Pd(0)(PPh₃)₂/DPEphos catalyst.

ACS Catalysis 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, Category: naphthyridine.

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

Stock, Nicholas published the artcileThe geminal dimethyl analogue of Flurbiprofen as a novel Aβ₄₂ inhibitor and potential Alzheimer’s disease modifying agent, Recommanded Product: Sulindac sulfone, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(8), 2219-2223, database is CAplus and MEDLINE.

The subtle modification of a selection of Aβ₄₂ inhibiting non-steroidal anti-inflammatory drugs (NSAIDs), through synthesis of the geminal di-Me analogs, was anticipated to ablate their cyclooxygenase activity while maintaining Aβ₄₂ inhibition. Methylflurbiprofen I exhibited similar in vitro Aβ₄₂ inhibition to its parent NSAID Flurbiprofen and was further evaluated in the Tg2576 mouse model of Alzheimer’s disease and an animal model of gastro-intestinal (GI) impairment, but proved unviable for further clin. development.

Bioorganic & Medicinal Chemistry Letters 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 C16H10O5, Recommanded Product: Sulindac sulfone.

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

Richter, Luise published the artcileAmyloid-β 42 peptide (Aβ42)-lowering compounds directly bind to Aβ and interfere with amyloid precursor protein (APP) transmembrane dimerization, Recommanded Product: Sulindac sulfone, the publication is Proceedings of the National Academy of Sciences of the United States of America (2010), 107(33), 14597-14602, S14597/1-S14597/6, database is CAplus and MEDLINE.

Following ectodomain shedding by p-secretase, successive proteolytic cleavages within the transmembrane sequence (TMS) of the amyloid precursor protein (APP) catalyzed by γ-secretase result in the release of amyloid-β (Aβ) peptides of variable length. AP peptides with 42 amino acids appear to be the key pathogenic species in Alzheimer’s disease, as they are believed to initiate neuronal degeneration. Sulindac sulfide, which is known as a potent γ-secretase modulator (GSM), selectively reduces Aβ42 production in favor of shorter Aβ species, such as Aβ38. By studying APP-TMS dimerization we previously showed that an attenuated interaction similarly decreased Aβ42 levels and concomitantly increased Aβ38 levels. However, the precise mol. mechanism by which GSMs modulate Aβ production is still unclear. In this study, using a reporter gene-based dimerization assay, we found that APP-TMS dimers are destabilized by sulindac sulfide and related Aβ42-lowering compounds in a concentration-dependent manner. By surface plasmon resonance anal. and NMR spectroscopy, we show that sulindac sulfide and novel sulindac-derived compounds directly bind to the AD sequence. Strikingly, the attenuated APP-TMS interaction by GSMs correlated strongly with Aβ42-lowering activity and binding strength to the Aβ sequence. Mol. docking analyses suggest that certain GSMs bind to the GxxxG dimerization motif in the APP-TMS. We conclude that these GSMs decrease Aβ42 levels by modulating APP-TMS interactions. This effect specifically emphasizes the importance of the dimeric APP-TMS as a promising drug target in Alzheimer’s disease.

Proceedings of the National Academy of Sciences of the United States of America 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

Kawabata, Kyuichi published the artcileNobiletin, a citrus flavonoid, down-regulates matrix metalloproteinase-7 (matrilysin) expression in HT-29 human colorectal cancer cells, Safety of Sulindac sulfone, the publication is Bioscience, Biotechnology, and Biochemistry (2005), 69(2), 307-314, database is CAplus and MEDLINE.

Overexpression of matrix metalloproteinases (MMPs) is associated with cancer metastasis. We assessed mRNA expression of MMPs in six human colorectal cancer cell lines and found a considerable level of MMP-7 expression in HT-29 cells. Next, we searched for natural and synthetic compounds that cause a reduction in the production of proMMP-7 protein, and found that nobiletin (NOB), quercetin, valeryl salicylate, and sulindac sulfone demonstrated marked inhibition. Importantly, NOB attenuated proMMP-7 protein and its mRNA expression both concentration- and time-dependently via a reduction of activator protein-1 (AP-1) DNA binding activity, suggesting it as a promising agent for suppression of cancer cell invasion and metastasis through MMP-7 gene repression.

Bioscience, Biotechnology, and Biochemistry 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, Safety of Sulindac sulfone.

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

Ki, Han Kwon published the artcileSuppressive effects of natural and synthetic agents on dextran sulfate sodium-induced interleukin-1β release from murine peritoneal macrophages, Related Products of naphthyridine, the publication is Bioscience, Biotechnology, and Biochemistry (2004), 68(2), 436-439, database is CAplus.

Interleukin (IL)-1β, an anti-apoptotic and pro-inflammatory cytokine, plays an important role in the onset of inflammation-associated disease. We examined the suppressive effects of a total of 39 synthetic or natural compounds on dextran sulfate sodium-induced IL-1β production in murine peritoneal macrophages. Several compounds, including α-tocopherol, gallic acid, (-)-catechin and rutin, were highly effective for attenuating IL-1β production, suggesting that they would be useful for anti-inflammatory application.

Bioscience, Biotechnology, and Biochemistry 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, Related Products of naphthyridine.

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

Wen, Ziyi published the artcileThe ocular pharmacokinetics and biodistribution of phospho-sulindac (OXT-328) formulated in nanoparticles: Enhanced and targeted tissue drug delivery, Formula: C20H17FO4S, the publication is International Journal of Pharmaceutics (Amsterdam, Netherlands) (2019), 273-279, database is CAplus and MEDLINE.

We studied the pharmacokinetics, biodistribution and metabolism of phospho-sulindac (PS), a novel agent efficacious in the treatment of dry eye, formulated in nanoparticles (PS-NPs) following its topical administration to the eye of New Zealand White rabbits. The nanoparticles were spherical with effective diameter = 108.9 ± 41.7 nm, zeta potential = -21.70 ± 3.78 mV, drug loading = 7%, and entrapment efficiency = 46.4%. Of the total PS delivered topically to the eye, >95% was retained in the anterior segment, predominantly in the cornea (C_max = 101.3 μM; T_max = 1 h; T_1/2 = 2.6 h; area AUC_0-16h = 164.4 μM·h) and conjunctiva (C_max = 89.4 μM; T_max = 0.25 h; T_1/2 = 3.1 h; AUC_0-16h = 63.5 μM·h), the tissues most affected by dry eye disease. No PS or its metabolites were detected in the systemic circulation. PS was metabolized to PS sulfide and PS sulfone; all three mols. were hydrolyzed to sulindac, which was converted to sulindac sulfide and sulindac sulfone. A solution formulation of PS provided lower PS levels in ocular tissues but higher levels of PS metabolites, compared to PS-NPs. Therefore, NPs represent an effective formulation for the topical ocular administration of PS for anterior segment diseases, such as dry eye disease.

International Journal of Pharmaceutics (Amsterdam, Netherlands) 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 C9H4F6O, Formula: C20H17FO4S.

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