Month: December 2022

Wu, Peng published the artcileChromatographic Resolution of α-Amino Acids by (R)-(3,3′-Halogen Substituted-1,1′-binaphthyl)-20-crown-6 Stationary Phase in HPLC, Formula: C22H18O2, the publication is Chinese Journal of Chemistry (2017), 35(7), 1037-1042, database is CAplus.

Three new chiral stationary phases (CSPs) for high-performance liquid chromatog. were prepared from R-(3,3-halogen substituted-1,1-binaphthyl)-20-crown-6 (halogen = Cl, Br and I ). The exptl. results showed that R-(3,3-dibromo-1,1-binaphthyl)-20-crown-6 (CSP-1) possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives All twenty-one α-amino acids have different degrees of separation on R-(3,3-dibromo-1,1-binaphthyl)-20-crown-6-based CSP-1 at room temperature The enantioselectivity of CSP-1 is also better than those of some com. R-(1,1-binaphthyl)-20-crown-6 derivatives Both the separation factors (α) and the resolution (R_s) are better than those of com. crown ether-based CSPs [CROWNPAK CR(+) from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and valine, which cannot be separated by com. CR(+). This study proves the com. usefulness of the R-(3,3-dibromo-1,1-binaphthyl)-20-crown-6 chiral stationary phase.

Chinese Journal of 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 C18H26ClN3O, Formula: C22H18O2.

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

Xiao, Min published the artcileSynthesis of 2-borono-benzaldehyde-(2′-hydroxyl-4′-sulfonate) naphthalene hydrazone and recognition of Pb²⁺, Formula: C10H9NO4S, the publication is Fenxi Kexue Xuebao (2015), 31(6), 792-796, database is CAplus.

2-Borono-benzaldehyde-(2′-hydroxyl-4′-sulfonate) naphthalene hydrazone derivative 2-BBHSNH (the host 1) was designed and synthesized. Due to its good water solubility, the recognition system didn’t need any organic medium. Research results showed that 2-borono-benzaldehyde-(2′-hydroxyl-4′-sulfonate) naphthalene hydrazone possessed highly selective binding and recognition to Pb²⁺in KH₂PO₄-NaOH buffer solution (pH=6.0). The host 1 and Pb²⁺could form a 1:1 complex with strong fluorescence. The maximum emission wavelength of complex 1-Pb²⁺ was 568 nm and the binding constant was 4.3×10⁴ L·mol^-1. The presence of the other metal ions led fluorescence spectra of host 1 little change, such as Cu²⁺, Mn²⁺, Mg²⁺, Fe²⁺, Ca²⁺, Co²⁺, Ni²⁺, Hg²⁺, Cd²⁺, Ag⁺ and so on. Fluorescence intensity and the concentration of Pb²⁺ presented good linear relationship from 5.0×10^-7-1.0×10^-4 mol·L^-1 with a correlation coefficient of 0.9983, and the detection limit of method was 9.7×10^-8 mol·L^-1. The method was used to detect Pb²⁺in water sample from environment with the recovery of 111%-116%.

Fenxi Kexue Xuebao 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 C4H12ClNO, Formula: C10H9NO4S.

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

Xie, Gang published the artcileRegioselective oxidation of phospho-NSAIDs by human cytochrome P450 and flavin monooxygenase isoforms: implications for their pharmacokinetic properties and safety, Quality Control of 59973-80-7, the publication is British Journal of Pharmacology (2012), 167(1), 222-232, database is CAplus and MEDLINE.

Background and Purpose Phospho-ibuprofen (MDC-917) and phospho-sulindac (OXT-328) are highly effective in cancer and arthritis treatment in preclin. models. Here, we investigated their metabolism by major human cytochrome P450s (CYPs) and flavin monooxygenases (FMOs). Exptl. Approach The CYP/FMO-catalyzed metabolism of phospho-ibuprofen and phospho-sulindac was studied by using in silico prediction modeling and a direct exptl. approach. Key Results The CYP isoforms catalyze the oxidation of non-steroidal anti-inflammatory drugs (NSAIDs) and phospho-NSAIDs, with distinct activity and regioselectivity. CYP1A2, 2C19, 2D6 and 3A4 oxidize phospho-ibuprofen, but not ibuprofen; whereas CYP2C9 oxidizes ibuprofen, but not phospho-ibuprofen. All CYPs tested oxidize phospho-sulindac, but not sulindac. Among the five CYPs evaluated, CYP3A4 and 2D6 are the most active in the oxidation of phospho-ibuprofen and phospho-sulindac resp. FMOs oxidized phospho-sulindac and sulindac, but not phospho-ibuprofen or ibuprofen. FMOs were more active towards phospho-sulindac than sulindac, indicating that phospho-sulindac is a preferred substrate of FMOs. The susceptibility of phospho-NSAIDs to CYP/FMO-mediated metabolism was also reflected in their rapid oxidation by human and mouse liver microsomes, which contain a full complement of CYPs and FMOs. Compared with conventional NSAIDs, the higher activity of CYPs towards phospho-ibuprofen and phospho-sulindac may be due to their greater lipophilicity, a key parameter for CYP binding. Conclusions and Implications CYPs and FMOs play an important role in the metabolism of phospho-NSAIDs, resulting in differential pharmacokinetic profiles between phospho-NSAIDs and NSAIDs in vivo. The consequently more rapid detoxification of phospho-NSAIDs is likely to contribute to their greater safety.

British Journal of Pharmacology 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 C8H8BNO3, Quality Control of 59973-80-7.

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

Cheng, Ka-Wing published the artcileCurcumin enhances the lung cancer chemopreventive efficacy of phospho-sulindac by improving its pharmacokinetics, Recommanded Product: Sulindac sulfone, the publication is International Journal of Oncology (2013), 43(3), 895-902, database is CAplus and MEDLINE.

Phospho-sulindac (PS) is a safe sulindac derivative with promising anticancer efficacy in colon cancer. We evaluated whether its combination with curcumin could enhance the efficacy in the treatment of lung cancer. Curcumin, the principal bioactive component in turmeric, has demonstrated versatile capabilities to modify the therapeutic efficacy of a wide range of anticancer agents. Here, we evaluated the effect of co-administration of curcumin on the anticancer activity of PS in a mouse xenograft model of human lung cancer. Curcumin enhanced the cellular uptake of PS in human lung and colon cancer cell lines. To assess the potential synergism between curcumin and PS in vivo, curcumin was suspended in 10% Tvveen-80 or formulated in micellar nanoparticles and given to mice by oral gavage prior to the administration of PS. Both formulations of curcumin significantly improved the pharmacokinetic profiles of PS, with the 10% Tween-80 suspension being much more effective than the nanoparticle formation. However, curcumin did not exhibit any significant modification of the metabolite profile of PS. Furthermore, in a mouse s.c. xenograft model of human lung cancer, PS (200 mg/kg) in combination with curcumin (500 mg/kg) suspended in 10% Tween-80 (51% inhibition, p<0.05) was significantly more efficacious than PS plus micelle curcumin (30%) or PS (25%) or curcumin alone (no effect). Consistent with the improved pharmacokinetics, the combination treatment group had higher levels of PS and its metabolites in the xenografts compared to PS alone. Our results show that curcumin substantially improves the pharmacokinetics of PS leading to synergistic inhibition of the growth of human lung cancer xenografts, representing a promising drug combination.

International Journal of Oncology 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

Cheng, Ka Wing published the artcileAerosol Administration of Phospho-Sulindac Inhibits Lung Tumorigenesis, Category: naphthyridine, the publication is Molecular Cancer Therapeutics (2013), 12(8), 1417-1428, database is CAplus and MEDLINE.

Phospho-sulindac is a sulindac derivative with promising anticancer activity in lung cancer, but its limited metabolic stability presents a major challenge for systemic therapy. We reasoned that inhalation delivery of phospho-sulindac might overcome first-pass metabolism and produce high levels of intact drug in lung tumors. Here, we developed a system for aerosolization of phospho-sulindac and evaluated the antitumor efficacy of inhaled phospho-sulindac in an orthotopic model of human non-small cell lung cancer (A549 cells). We found that administration by inhalation delivered high levels of phospho-sulindac to the lungs and minimized its hydrolysis to less active metabolites. Consequently, inhaled phospho-sulindac (6.5 mg/kg) was highly effective in inhibiting lung tumorigenesis (75%; P < 0.01) and significantly improved the survival of mice bearing orthotopic A549 xenografts. Mechanistically, phospho-sulindac suppressed lung tumorigenesis by (i) inhibiting EGF receptor (EGFR) activation, leading to profound inhibition of Raf/MEK/ERK and PI3K/AKT/mTOR survival cascades; (ii) inducing oxidative stress, which provokes the collapse of mitochondrial membrane potential and mitochondria-dependent cell death; and (iii) inducing autophagic cell death. Our data establish that inhalation delivery of phospho-sulindac is an efficacious approach to the control of lung cancer, which merits further evaluation. Mol Cancer Ther; 12(8); 1417-28. ©2013 AACR.

Molecular Cancer Therapeutics 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

Zhang, Huaiyuan published the artcileOxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones, Quality Control of 2960-93-2, the publication is Chemistry – A European Journal (2022), 28(21), e202200181, database is CAplus and MEDLINE.

Much attention was focused on developing the synthetic methods to prepare xanthene derivatives. Binaphthyl-based xanthene derivatives, e.g., I (R = H), were prepared through the oxidation of BINOLs promoted by the hypervalent iodine reagent iodosylbenzene (PhIO). Nine-membered lactones, e.g., II, were obtained through a similar oxidative reaction when iodoxybenzene (PhIO₂) was used. Addnl., one-pot reactions of BINOLs, PhIO and nucleophiles such as alcs. and amines were also investigated to provide alkoxylated products,e.g., I (R = Me). and amides, e.g, III. in good to excellent yields.

Chemistry – A European Journal 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 C10H14O, Quality Control of 2960-93-2.

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

Sap, Jeroen B. I. published the artcileSynthesis of ¹⁸F-difluoromethylarenes using arylboronic acids, ethyl bromofluoroacetate and [¹⁸F]fluoride, Recommanded Product: 1-(Difluoromethyl)naphthalene, the publication is Chemical Science (2019), 10(11), 3237-3241, database is CAplus and MEDLINE.

Herein, the radiosynthesis of ¹⁸F-difluoromethylarenes RCHF¹⁸F (R = 4-C₂H₅, 4-OC₆H₅, 3,5-CH₃, etc.) via the assembly of three components, a boron reagent, Et bromofluoroacetate, and cyclotron-produced non-carrier added [¹⁸F]fluoride was reported. The two key steps are a copper-catalyzed cross-coupling reaction, and a Mn-mediated ¹⁸F-fluorodecarboxylation.

Chemical Science 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

Sheng, Huaming published the artcileIdentification of the Sulfone Functionality in Protonated Analytes via Ion/Molecule Reactions in a Linear Quadrupole Ion Trap Mass Spectrometer, Safety of Sulindac sulfone, the publication is Journal of Organic Chemistry (2014), 79(7), 2883-2889, database is CAplus and MEDLINE.

A tandem mass spectrometric method is presented for the rapid identification of drug metabolites that contain the sulfone functional group. This method is based on a gas-phase ion/mol. reaction of protonated sulfone analytes with tri-Me borate (TMB) that yields a diagnostic product ion, adduct-Me₂O, at high reaction efficiency. A variety of compounds with different functional groups, such as sulfoxides, hydroxylamines, N-oxides, anilines, phenol, an aliphatic amine, and an aliphatic alc., were examined to probe the selectivity of this reaction. Except for protonated sulfones, most of the protonated compounds react very slowly or not at all with TMB. Most importantly, none of them give the adduct-Me₂O product. A mechanism that explains the observed selectivity is proposed for the diagnostic reaction and is supported by quantum chem. calculations The reaction was tested with the anti-inflammatory drug sulindac and its metabolite, sulindac sulfone, which were readily distinguished. The presence of other functionalities in addition to sulfone was found not to influence the diagnostic reactivity.

Journal of Organic 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 C20H28B2O4S2, Safety of Sulindac sulfone.

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

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