Month: November 2022

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

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

Lamm, Jan-Hendrik published the artcilePolyalkynylanthracenes – syntheses, structures and their behaviour towards UV irradiation, HPLC of Formula: 18512-55-5, the publication is Organic & Biomolecular Chemistry (2014), 12(37), 7355-7365, database is CAplus and MEDLINE.

A series of bis- and tris[(trimethylsilyl)ethynyl]anthracenes (1,5-, 1,8-, 9,10- and 1,8,10-) has been synthesized by multistep (cross coupling) reactions and the behavior of the SiMe₃-functionalised alkynylanthracene derivatives towards UV irradiation was qual. studied by NMR spectroscopy. In the case of 9,10-bis[(trimethylsilyl)ethynyl]anthracene we observed a photodimerization upon UV irradiation; the third example was reported for a sym. 9,10-difunctionalised anthracene derivative, besides those with small fluorine- and methyl-substituents. The anthracene dimerization is completely thermally reversible and the temperature dependence of the cycloelimination reaction was studied by ¹H VT-NMR experiments The (deprotected) 1,5- and 1,8-diethynylanthracenes were converted with (dimethylamino)trimethylstannane to obtain the corresponding SnMe₃-functionalised alkynes, potentially useful as highly conjugated building blocks in Stille cross coupling reactions. The new anthracene compounds were completely characterised by multinuclear NMR spectroscopy, (high resolution) mass spectrometry and – in most cases – by X-ray diffraction experiments

Organic & Biomolecular Chemistry 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, HPLC of Formula: 18512-55-5.

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

Jesny, S. published the artcileElectrocatalytic resolution of guanine, adenine and cytosine along with uric acid on poly (4-amino-3-hydroxy naphthalene-1-sulfonic acid) modified glassy carbon electrode, Safety of 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, the publication is Journal of Electroanalytical Chemistry (2017), 153-161, database is CAplus.

A simple, easy to fabricate, selective and sensitive sensor for simultaneous determination of nucleic acid bases guanine, adenine and cytosine along with uric acid is being reported. Glassy C electrode with an electropolymerized layer of 4-amino-3-hydroxy naphthalene-1-sulfonic acid could resolve the oxidation peaks of uric acid, guanine, adenine and cytosine using 0.1M NaOH as supporting electrolyte. The electrocatalytic oxidation current is linear in the range from 10 μM-250 μM for uric acid, guanine and adenine and 80 μM-250 μM for cytosine with detection limit 9.31 μM, 0.93 μM, 6.20 μM and 9.20 μM resp. for simultaneous determination by square wave voltammetry. The diffusion coefficient of uric acid, guanine, adenine and cytosine in 0.1M NaOH was determined by chronoamperometry. The electrode processes are diffusion controlled, which eliminate the fouling effect produced by adsorption of these organic compounds on the electrode surface. The developed sensor has promising applications for real sample anal.

Journal of Electroanalytical 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, Safety of 4-Amino-3-hydroxynaphthalene-1-sulfonic acid.

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

Goswami, Shyamaprosad published the artcileThree-point hydrogen bondings of carboxyl group in recognition of carboxylic acid and amino acid with designed synthetic receptors, Synthetic Route of 14903-78-7, the publication is Journal of the Indian Chemical Society (1999), 76(11-12), 661-664, database is CAplus.

The binding of carboxylic acids and amino acids were reported with designed synthetic receptors. The 3-point binding of carboxylic acids (with receptors I–III) was used to bind acetylglycine with receptor 6.

Journal of the Indian Chemical Society 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, Synthetic Route of 14903-78-7.

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

Goswami, Shyamaprosad published the artcileN-Bromosuccinimide reactions of some heterocycles in the presence or absence of water: an overview of ring versus side chain bromination for the synthesis of important brominated heterocyclic synthons, COA of Formula: C10H10N2, the publication is Journal of Heterocyclic Chemistry (2001), 38(1), 173-178, database is CAplus.

Reactions of various heterocycles with N-bromosuccinimide in the presence or absence of water have been studied for side chain vs. ring bromination to afford some new and important heterocyclic synthons. Interestingly, the N-bromosuccinimide reaction of I in the presence of perchloric acid, a new condition, affords exclusively the new dibromoaminopicoline II, which is not obtained by other presently studied methods.

Journal of Heterocyclic Chemistry 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, COA of Formula: C10H10N2.

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

Goswami, S. published the artcileRecognition of insoluble tartaric acid in chloroform, Application In Synthesis of 14903-78-7, the publication is Tetrahedron (2001), 57(23), 4987-4993, database is CAplus.

Simple receptors for the recognition and solubilization of insoluble tartaric acid in chloroform were designed and synthesized for the 1st time. Receptors N-(7-Methyl-[1,8]naphthylridin-2-yl)-N‘-(6-methylpyridin-2-yl)isophthalamide and N,N‘-Bis(7-methyl-[1,8]naphthylridin-2-yl)isophthalamide were successful in solubilizing tartaric acid into chloroform forming a 1:1 complex, and also are useful as fluorescent probes for the detection of this substrate.

Tetrahedron 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

Liou, Jun-Yang published the artcileNonsteroidal Anti-inflammatory Drugs Induce Colorectal Cancer Cell Apoptosis by Suppressing 14-3-3ε, Category: naphthyridine, the publication is Cancer Research (2007), 67(7), 3185-3191, database is CAplus and MEDLINE.

To determine the role of 14-3-3 in colorectal cancer apoptosis induced by nonsteroidal anti-inflammatory drugs (NSAIDs), we evaluated the effects of sulindac on 14-3-3ε protein expression in colorectal cancer cells. Sulindac sulfide inhibited 14-3-3ε proteins in HT-29 and DLD-1 cells in a time- and concentration-dependent manner. Sulindac sulfone at 600 μmol/L inhibited 14-3-3ε protein expression in HT-29. Indomethacin and SC-236, a selective cyclooxygenase-2 (COX-2) inhibitor, exerted a similar effect as sulindac. Sulindac suppressed 14-3-3ε promoter activity. As 14-3-3ε promoter activation is mediated by peroxisome proliferator-activated receptor δ (PPARδ), we determined the correlation between 14-3-3ε inhibition and PPARδ suppression by NSAIDs. Sulindac sulfide inhibited PPARδ protein expression and PPARδ transcriptional activity. Overexpression of PPARδ by adenoviral transfer rescued 14-3-3ε proteins from elimination by sulindac or indomethacin. NSAID-induced 14-3-3ε suppression was associated with reduced cytosolic Bad with elevation of mitochondrial Bad and increase in apoptosis which was rescued by Ad-PPARδ transduction. Stable expression of 14-3-3ε in HT-29 significantly protected cells from apoptosis. Our findings shed light on a novel mechanism by which NSAIDs induce colorectal cancer apoptosis via the PPARδ/14-3-3ε transcriptional pathway. These results suggest that 14-3-3ε is a target for the prevention and therapy of colorectal cancer.

Cancer 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, Category: naphthyridine.

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

Mesches, Michael H. published the artcileSulindac improves memory and increases NMDA receptor subunits in aged Fischer 344 rats, Safety of Sulindac sulfone, the publication is Neurobiology of Aging (2004), 25(3), 315-324, database is CAplus and MEDLINE.

Inflammatory processes in the central nervous system are thought to contribute to Alzheimer’s disease (AD). Chronic administration of nonsteroidal anti-inflammatory drugs (NSAIDs) decreases the incidence of Alzheimer’s disease. There are very few studies, however, on the cognitive impact of chronic NSAID administration. The N-methyl-D-aspartate (NMDA) receptor is implicated in learning and memory, and age-related decreases in the NMDA NR2B subunit correlate with memory deficits. Sulindac, an NSAID that is a nonselective cyclooxygenase (COX) inhibitor was chronically administered to aged Fischer 344 rats for 2 mo. Sulindac, but not its non-COX active metabolite, attenuated age-related deficits in learning and memory as assessed in the radial arm water maze and contextual fear conditioning tasks. Sulindac treatment also attenuated an age-related decrease in the NR1 and NR2B NMDA receptor subunits and prevented an age-related increase in the pro-inflammatory cytokine, interleukin 1β (IL-1β), in the hippocampus. These findings support the inflammation hypothesis of aging and have important implications for potential cognitive enhancing effects of NSAIDs in the elderly.

Neurobiology of Aging 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

Tinsley, Heather N. published the artcileColon tumor cell growth-inhibitory activity of sulindac sulfide and other nonsteroidal anti-inflammatory drugs is associated with phospphodiesterase 5 inhibition, Synthetic Route of 59973-80-7, the publication is Cancer Prevention Research (2010), 3(10), 1303-1313, database is CAplus and MEDLINE.

Nonsteroidal anti-inflammatory drugs (NSAID) display promising antineoplastic activity, but toxicity resulting from cyclooxygenase (COX) inhibition limits their clin. use for chemoprevention. Studies suggest that the mechanism may be COX independent, although alternative targets have not been well defined. Here, we show that the NSAID sulindac sulfide (SS) inhibits cyclic guanosine 3′,5′-monophosphate (cGMP) phosphodiesterase (PDE) activity in colon tumor cell lysates at concentrations that inhibit colon tumor cell growth in vitro and in vivo. A series of chem. diverse NSAIDs also inhibited cGMP hydrolysis at concentrations that correlate with their potency to inhibit colon tumor cell growth, whereas no correlation was observed with COX-2 inhibition. Consistent with its selectivity for inhibiting cGMP hydrolysis compared with cAMP hydrolysis, SS inhibited the cGMP-specific PDE5 isoenzyme and increased cGMP levels in colon tumor cells. Of numerous PDE isoenzyme-specific inhibitors evaluated, only the PDE5-selective inhibitor MY5445 inhibited colon tumor cell growth. The effects of SS and MY5445 on cell growth were associated with inhibition of β-catenin-mediated transcriptional activity to suppress the synthesis of cyclin D and survivin, which regulate tumor cell proliferation and apoptosis, resp. SS had minimal effects on cGMP PDE activity in normal colonocytes, which displayed reduced sensitivity to SS and did not express PDE5. PDE5 was found to be overexpressed in colon tumor cell lines as well as in colon adenomas and adenocarcinomas compared with normal colonic mucosa. These results suggest that PDE5 inhibition, cGMP elevation, and inhibition of β-catenin transcriptional activity may contribute to the chemopreventive properties of certain NSAIDs.

Cancer Prevention 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 C9H16BNO2, Synthetic Route of 59973-80-7.

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