Category: naphthyridine

Stevens, Loah A. published the artcileTemperature-Mediated Polymorphism in Molecular Crystals: The Impact on Crystal Packing and Charge Transport, Computed Properties of 152873-79-5, the publication is Chemistry of Materials (2015), 27(1), 112-118, database is CAplus.

The authors report a novel synthesis to ultra high purity 7,14-bis((trimethylsilyl)ethynyl)dibenzo[b,def]chrysene (TMS-DBC) and the use of this material in the growth of single crystals by solution and vapor deposition techniques. The substrate temperature has a dramatic impact on the crystal growth, producing two distinct polymorphs of TMS-DBC; low temperature (LT) fine red needles and high temperature (HT) large yellow platelets. Single crystal x-ray crystallog. confirms packing structures where the LT crystals form a 1-dimensional slipped-stack structure, while the HT crystals adopt a 2-dimensional brickwork motif. Crystallog. data are given. These polymorphs also represent a rare example where both are extremely stable and do not interconvert to the other crystal structure upon solvent or thermal annealing. Single crystal organic field-effect transistors of the LT and HT crystals show that the HT 2-dimensional brickwork motif produces hole mobilities â‰?.1 cm² V^-1 s^-1, while the mobility of the 1-dimensional structure is significantly lower, at 0.028 cm² V^-1 s^-1. Electronic-structure calculations indicate that the superior charge transport in the brickwork polymorph in comparison to the slipped-stack polymorph is due to the presence of an increased dimensionality of the charge migration pathways.

Chemistry of Materials published new progress about 152873-79-5. 152873-79-5 belongs to naphthyridine, auxiliary class Trifluoromethyl,Sulfonate,Benzene, name is 1,5-NAphthalenebis(trifluoromethanesulfonate), and the molecular formula is C5H3F2NO3, Computed Properties of 152873-79-5.

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

Clarkson, R. G. published the artcileSpirans with four aromatic radicals on the spiro carbon atom, Product Details of C25H16O, the publication is Journal of the American Chemical Society (1930), 2881-91, database is CAplus.

2-NCC₆H₄Ph, b₄₃ 202-4°, m. 35-6°, with PhMgBr gives 76% of 2-PhC₆H₄Bz, reduced by Mg-MgI₂ to 9-phenyl-fluorene (25% yield) and gives with PhMgBr 63% of 2-phenyltriphenylcarbinol, m. 87-8°; it can be distilled with steam only if every trace of acid is previously removed. Attempts to prepare the chloride, even with AcCl at 0°, gives 9,9-diphenylfluorene. 2,3′,3”-Triphenyltriphenylcarbinol, from 3-BrC₆H₄Ph and 2-PhC₆H₄CO₂Et, could not be crystallized; heating with AcOH containing a little concentrated H₂SO₄ gives 9,9-di[3-biphenyl]-fluorene, m. 190-1°. 2-IMgC₆H₄Ph and fluorenone give 70% of 9-[2-biphenyl]-9-fluorenol, m. 160-70°, crystallizes unchanged from; AcOH; AcOH containing a trace of HCl or I gives 9,9′-spirobifluorene, C₂₆H₁₆, m. AcCl in C₆H₆ gives the same compound; it is not affected by Zn in AcOH and does not add Br. 2-Iododiphenyl ether, from the 2-NO₂ derivative by reduction and the Sandmeyer reaction, b₂₂ 198-202°. m. 54-6°; the Grignard reagent with fluorenone gives 9-[2-phenoxyphenyl]-9-fluorenol, slightly brown, m. 154°; with AcCl in AcOH this yields spiro-9-fluorene-9′-xanthene (I), m. 212-3°. A definite proof of the course of the condensation reaction is afforded by the synthesis of I from xanthone. 2-IMgC₆H₄Ph and xanthone give 9-[2-biphenyl-9-xanthenol, isolated as the mol. compound with xanthone; warming this with AcOH gives I. 2-Iodo-4′-methyldiphenyl ether, b₃₄, 210-5°, m. 41° (74% yield from the NO₂ derivative); the Grignard reagent with 2-bromofluorenone gives 9-[2-phenyl p-tolyl ether)-6-bromo-9-fluorenol, pale yellow, m. 175°; heating with glacial AcOH containing a little HCl gives spiro-9-[2-bromofluorene]-9′[-[2′-methylxanthene], m. 201°; the Me group could not be oxidized without destroying the spiran linkage. 2-lMgC₆H₄Ph and xanthone give 9-[2-phenoxyphenyl]-9-xanthenol, m. 136-7°; heating with AcOH 3 hrs. gives 9,9′-spirobixanthene, m. 283-4°; no evidence of salt formation was observed with dry HBr or HClO₄. Reduction of 2-BrC₆H₄Bz with Zn-Hg gives 50% of 2-bromodiphenylmethane (II), b₂₂ 192-8°, does not solidify at 0°; the Grignard reagent with fluorenone gives 9-[2-benzylphenyl]-9-fluorenol, m. 132-3°; AcOH-HCl gives spiro-9-fluorene-9′-[9,10-dihydroanthracene, m. 207°. II and xanthone give 9-[2-benzylphenyl]-9-xanthenol, m. 146°; AcCl and AcOH give spiro-9-xanthene-9′-[9,10-dihydroanthracene], m. 257-9° (corrected). 2-BrC₆H₄CHPh₂ yields a Grignard reagent after 24 hrs. boiling in Et₂O-PhMe which gives with fluorenone 51% of 9-[2-benzohydrylphenyl]-9-fluorenol, m. 192°; AcOH-HCl transforms this into spiro-9-fluorene-9′-[10-Phenyl-9,10-dihydroanthracene), m. 267-8° (corrected), 9-[2-Benzohydrylphenyl]-9-xanthenol forms a mol. complex with xanthone, m. 200-5° decompn,); AcOH-HCl gives spiro-9-xanthene-9′-[10-phenyl-9,10-dihydroanthracene], m. 334-5° (corrected). [2-IMg-C₆H₄Ph and 10,10′-diphenylanthrone gives 55% of 9-[2-biphenyl]-10,10 diphenyl 9,10-dihydro-9-anthranol slightly yellow, m. 231-4° (decomposition); boiling AcOH gives quant. spiro-9-fluorene-9′-[10,10-diphenyl-9,10-dihydroanthracene), m. 363-4° (corrected). 2-IMg-C₆H₄OPh and diphenylanthrone give 74% of 9-[2-phenoxyphenyl]-10,10-diphenyl-9,10-dihydro-9-anthranol, m. 270-8° (corrected); AcOH gives quant. spiro-9-xanthene-9′-[10,10-diphenyl-9,10-dihydroanthracene], m. 377-80° (corrected). 2-IMgC₆H₄Ph and anthraquinone gives 25% of 9,10-di-[2-biphenyl]anthraquinol, m. 353-5° (corrected, decomposition); heating with AcOH-AcCl 4 hrs. gives quant. dispiro-9,9′-difluorene-9”,9”’-[9,10-di-hydroanthracene], m. 471-4° (corrected). 9,10-Di[2-phenoxyphenyl]anthraquinol, m. 351-3° (corrected, decomposition) (47% yield; heating with AcOH-H₂SO₄ 8 hrs. on the steam bath gives 70% of dispiro-9,9′-dixanthene-9”,9”’-(9,10-dihydroanthracene), m. 487-90° (corrected). 2-IMgC₆H₄Ph and acenaphthoquinone give 32% of 7,8-di[2-biphenyl]acenaphthodiol, slightly yellow, m. 168°; AcOH-HCl does not give the expected dispiran but the pinacolin, C₃₆H₂₄O, m. 265-7° (corrected); hydrolysis of the latter with EtOH-KOH gives an acid, m. 252-4°(corrected). All the spirans are characterized by unusually high m. ps. and by extremely low insolubility

Journal of the American Chemical Society 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, Product Details of C25H16O.

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

Costa, David published the artcileSinglet oxygen scavenging activity of non-steroidal anti-inflammatory drugs, Product Details of C20H17FO4S, the publication is Redox Report (2008), 13(4), 153-160, database is CAplus and MEDLINE.

It has long been known that singlet oxygen (¹O₂) is generated during inflammatory processes. Once formed in substantial amounts, ¹O₂ may have an important role in mediating the destruction of infectious agents during host defense. On the other hand, ¹O₂ is capable of damaging almost all biol. mols. and is particularly genotoxic, which gives a special relevance to the scavenging of this ROS throughout anti-inflammatory treatments. Considering that the use of non-steroidal anti-inflammatory drugs (NSAIDs) constitutes a first approach in the treatment of persistent inflammatory processes (due to their ability to inhibit cyclooxygenase), a putative scavenging activity of NSAIDs for ¹O₂ would also represent a significant component of their therapeutic effect. The aim of the present study was to evaluate the scavenging activity for ¹O₂ by several chem. families of NSAIDs. The results suggested that the pyrazole derivatives (dipyrone and aminopyrine) are, by far, the most potent scavengers of ¹O₂ (much more potent compared to the other tested NSAIDs), displaying IC₅₀-values in the low micromolar range. There was a lack of activity for most of the arylpropionic acid derivatives tested, with only naproxen and indoprofen displaying residual activities, as for the oxazole derivative, oxaprozin. On the other hand, the pyrrole derivatives (tolmetin and ketorolac), the indolacetic acid derivatives (indomethacin, and etodolac), as well as sulindac and its metabolites (sulindac sulfide and sulindac sulfone) displayed scavenging activity in the high micromolar range. Thus, the scavenging effect observed for dipyrone and aminopyrine will almost certainly contribute to their healing effect in the treatment of prolonged or chronic inflammation, while that of the other studied NSAIDs may have a lower contribution, though these assumptions still require further in vivo validation.

Redox Report 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

Costa, David published the artcileHydrogen peroxide scavenging activity by non-steroidal anti-inflammatory drugs, Quality Control of 59973-80-7, the publication is Life Sciences (2005), 76(24), 2841-2848, database is CAplus and MEDLINE.

Hydrogen peroxide (H₂O₂) was shown to be formed during inflammatory processes and is implicated in its pathophysiol. Thus, a putative scavenging activity against this reactive oxygen specie (ROS) by anti-inflammatory drugs may be of great therapeutical value. The present study was undertaken to evaluate the scavenging activity for H₂O₂ by several non-steroidal anti-inflammatory drugs (NSAIDs), namely indomethacin, acemetacin, etodolac, tolmetin, ketorolac, oxaprozin, sulindac, and its metabolites sulindac sulfide and sulindac sulfone. The H₂O₂ scavenging assay was performed by measuring H₂O₂-elicited lucigenin chemiluminescence using a microplate reader. The specificity of the method was confirmed by the use of catalase, which completely prevented the H₂O₂-induced lucigenin chemiluminescence. The endogenous antioxidants melatonin and reduced glutathione (GSH) were used as pos. controls. The obtained results demonstrated that all the studied NSAIDs display H₂O₂ scavenging activity, although in different extents. The ranking order of potency found was sulindac sulfone > sulindac sulfide > GSH > sulindac > indomethacin > acemetacin > etodolac > oxaprozin > ketorolac â‰?melatonin > tolmetin.

Life Sciences 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

Martin, Timothy J. published the artcileHigh Throughput Biodegradation-Screening Test To Prioritize and Evaluate Chemical Biodegradability, HPLC of Formula: 116-63-2, the publication is Environmental Science & Technology (2017), 51(12), 7236-7244, database is CAplus and MEDLINE.

Comprehensive assessment of environmental biodegradability of pollutants is limited by the use of low-throughput systems. These are epitomized by OECD Ready Biodegradability Tests (RBTs), where one sample from an environment may be used to assess a chem.’s ability to readily biodegrade or persist universally in that environment. This neglects the considerable inherent microbial variation spatially and temporally in any environment. Inaccurate designations of biodegradability or persistence can occur as a result. RBTs are central in assessing biodegradation fate of chems. and inferring exposure concentrations in environmental risk assessments. We developed a colorimetric assay for the reliable quantification of suitable aromatic compounds in a high throughput biodegradation screening test (HT-BST). The HT-BST accurately differentiated and prioritized a range of structurally diverse aromatic compounds based on their assigned relative biodegradabilities and Quant. Structure-Activity Relationship (QSAR) model outputs. Approx. 20,000 individual biodegradation tests were performed, returning analogous results to conventional RBTs. The effect of substituent group structure and position on biodegradation potential demonstrated a significant correlation (P<0.05) with Hammett’s constant for substituents on position 3 of the phenol ring. The HT-BST may facilitate the rapid screening of 100,000 chems. reportedly manufactured in Europe and reduce the need for higher-tier fate and effects tests.

Environmental Science & Technology 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 C10H9NO4S, HPLC of Formula: 116-63-2.

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

Deolka, Shubham published the artcilePhotoinduced Trifluoromethylation of Arenes and Heteroarenes Catalyzed by High-Valent Nickel Complexes, Application In Synthesis of 14903-78-7, the publication is Angewandte Chemie, International Edition (2021), 60(46), 24620-24629, database is CAplus and MEDLINE.

Authors describe a series of air-stable Ni^III complexes supported by a simple, robust naphthyridine-based ligand. Access to the high-valent oxidation state is enabled by the CF₃ ligands on the nickel, while the naphthyridine exhibits either a monodentate or bidentate coordination mode that depends on the oxidation state and sterics, and enables facile aerobic oxidation of NiII to NiIII. These Ni^III complexes act as efficient catalysts for photoinduced C(sp²)-H bond trifluoromethylation reactions of (hetero)arenes using versatile synthetic protocols. This blue LED light-mediated catalytic protocol proceeds via a radical pathway and demonstrates potential in the late-stage functionalization of drug analogs.

Angewandte Chemie, International Edition published new progress about 14903-78-7. 14903-78-7 belongs to naphthyridine, auxiliary class 6.6_Aromatics,Naphthyridines, name is 2,7-Dimethyl-1,8-naphthyridine, and the molecular formula is C10H10N2, Application In Synthesis of 14903-78-7.

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

Gupta, Pankaj published the artcileGraphene and Co-polymer composite based molecularly imprinted sensor for ultratrace determination of melatonin in human biological fluids, Safety of 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, the publication is RSC Advances (2015), 5(50), 40444-40454, database is CAplus.

A novel molecularly imprinted polymer (MIP) sensor based on a composite of graphene (GR) and a co-polymer of 4-amino-3-hydroxy-1-naphthalenesulfonic acid (AHNSA) and melamine (MM) has been fabricated for detecting melatonin. The MIP film was fabricated by the deposition of a graphene layer on a glassy carbon electrode (GCE) surface followed by electropolymg. AHNSA and MM in the presence of melatonin. The morphol. of the sensor was characterized by using Field Emission-SEM (FE-SEM) and Electrochem. Impedance Spectroscopy (EIS). The electrochem. performance of the imprinted sensor was investigated by using cyclic voltammetry and square wave voltammetry. The electropolymerization conditions, method of template removal, effect of template to monomer ratio and incubation time were optimized. Electrochem. results showed that the oxidation peak current increased linearly with the concentration of melatonin in the range 0.05 to 100 μM L^-1. The detection limit of the imprinted electrochem. sensor towards the melatonin determination is calculated to be 60 × 10^-10 mol L^-1. The suitability of the GR/MIP based sensor has been demonstrated in detecting melatonin in biol. samples.

RSC Advances 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 C10H9NO4S, Safety of 4-Amino-3-hydroxynaphthalene-1-sulfonic acid.

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

Zhou, Shengyang published the artcileSynthesis of Fluorinated Poly(phenyl-alkane)s of Intrinsic Microporosity by Regioselective Aldehyde (A₂) + Aromatics (B₂) Friedel-Crafts Polycondensation, Application In Synthesis of 2960-93-2, the publication is Macromolecules (Washington, DC, United States) (2021), 54(13), 6543-6551, database is CAplus.

The design of functionalized porous materials is an important research direction in material science, especially for fluorine-containing materials with enhanced thermal/oxidative stability, lower dielec. constants, and better gas-selective permeation. In this work, a series of poly(phenyl-alkane)s of intrinsic microporosity (PIM-xR) were synthesized by the methanesulfonic acid-catalyzed Friedel-Crafts hydroxyalkylation polycondensation of contorted and rigid multibenzene and benzaldehyde derivatives The PIM-xR exhibited good thermal stability, excellent solution processability, and high Brunauer-Emmett-Teller (BET) surface areas (400-1200 m² g^-1). The physicochem. properties and applications of PIM-xR could be tuned by the type, quantity, distribution, and postmodification of substituents on the benzaldehyde derivatives Unlike other contorted and rigid multibenzene derivatives, only electron-rich spirobiindane derivatives directly produced soluble, linear, high-mol.-weight polymers without crosslinking because spirobisindane possesses three t-butyl-like structural units that provide large steric hindrance at potential reactive sites. Subsequently, a series of fluorinated PIMs (PIM-xF) with different fluorine contents and distributions were explored, and the relationship between the microporosity of PIM-xR and degrees of rotational freedom of the polymer chains was analyzed using these PIM-xF. Flexible and transparent PIM-xF membranes were easily obtained by solution processing and exhibited high gas permeabilities and moderate permeability selectivity. In particular, the CO₂/N₂ separation performance of the PIM-5F membrane exceeded the 2008 Robeson’s upper bound (P_CO2 = 3240 barrer and α_(CO2_/N2₎ = 27.9). This work provides a facile method for the precise design and preparation of fluorinated or other functionalized porous materials for environmental and energy applications.

Macromolecules (Washington, DC, United States) 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 C40H35N7O8, Application In Synthesis of 2960-93-2.

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

Xu, Chang published the artcileDifluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel, Synthetic Route of 53731-26-3, the publication is Nature Communications (2018), 9(1), 1-10, database is CAplus and MEDLINE.

Relatively low reactivity hinders using chlorodifluoromethane (ClCF₂H) for general difluoromethylation with organic mols., despite its availability as an inexpensive industrial chem. To date, transformations of ClCF₂H are very limited and most of them involve difluorocarbene intermediate. Here, a strategy for difluoromethylation of aromatics through nickel-catalyzed cross-coupling of ClCF₂H with readily accessible (hetero)aryl chlorides is described. The reaction proceeds under mild reaction conditions with high efficiency and features synthetic simplicity without preformation of arylmetals and broad substrate scope, including a variety of heteroaromatics and com. available pharmaceuticals. The reliable practicability and scalability of the current nickel-catalyzed process has also been demonstrated by several 10-g scale reactions without loss of reaction efficiency. Preliminary mechanistic studies reveal that the reaction starts from the oxidative addition of aryl chlorides to Ni(0) and a difluoromethyl radical is involved in the reaction, providing a route for applications of ClCF₂H in organic synthesis and related chem.

Nature Communications 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 C2H4ClNO, Synthetic Route of 53731-26-3.

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

He, Yantao published the artcileA potent and selective inhibitor for the UBLCP1 proteasome phosphatase, Computed Properties of 116-63-2, the publication is Bioorganic & Medicinal Chemistry (2015), 23(12), 2798-2809, database is CAplus and MEDLINE.

The ubiquitin-like domain-containing C-terminal domain phosphatase 1 (UBLCP1) has been implicated as a neg. regulator of the proteasome, a key mediator in the ubiquitin-dependent protein degradation Small mol. inhibitors that block UBLCP1 activity would be valuable as research tools and potential therapeutics for human diseases caused by the cellular accumulation of misfold/damaged proteins. The authors report a salicylic acid fragment-based library approach aimed at targeting both the phosphatase active site and its adjacent binding pocket for enhanced affinity and selectivity. Screening of the focused libraries led to the identification of the first potent and selective UBLCP1 inhibitor I. Compound I exhibits an IC₅₀ of 1.0 μM for UBLCP1 and greater than 5-fold selectivity against a large panel of protein phosphatases from several distinct families. Importantly, the inhibitor possesses efficacious cellular activity and is capable of inhibiting UBLCP1 function in cells, which in turn up-regulates nuclear proteasome activity. These studies set the groundwork for further developing compound I into chem. probes or potential therapeutic agents targeting the UBLCP1 phosphatase.

Bioorganic & Medicinal Chemistry 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 C10H9NO4S, Computed Properties of 116-63-2.

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