- Binding Expedient of 2-carbamido-1,3-indandione to Nucleic Acids: Potential Fluorescent Probe
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Fluorescent and computational methods were used to elucidate the binding expedient of 2-carbamido-1,3-indandione (CAID) tautomers to nucleotides. The dependence of the fluorescence emission of CAID loaded nucleic acids sequences to compound concentration, temperature and time variation was investigated. It was found that the subject compound binds to nucleic acids but does not intercalate. According to our quantum-chemical calculations on the conjugation between CAID and nucleotides, the binding in the formed complexes may be through hydrogen bonds. Two possible types of complexes were considered—CAID to the phosphate group and CAID to the nucleobase. To estimate the binding affinity, the interaction energies of the formed complexes were calculated. Tautomer 2-carboamide-1-hydroxy-3-oxo-indane is preferred in the formation of complexes, and the phosphate group complexes were more stable. Generally, the guanosine and deoxyguanosine monophosphate complexes were the most preferred regardless of the complex type. Because of the lack of cytotoxic effect on untransformed cell lines of mouse embryo fibroblasts Balb/c 3T3 according to our previous report (Markova et al, (2017) Bulg Chem Commun, 49D, 221–226) and the affinity to nucleic acids, we can suggest that the subject compound could be suitable to be used as a novel type of fluorescent biomarker.
- Stoyanova, Nina,Markova, Nadezhda,Angelov, Ivan,Philipova, Irena,Enchev, Venelin
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- Direct detection of a triplet vinylnitrene, 1,4-naphthoquinone-2-ylnitrene, in solution and cryogenic matrices
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The photolysis of 2-azido-1,4-naphthoquinone (1) in argon matrices at 8 K results in the corresponding triplet vinylnitrene 32, which was detected directly by IR spectroscopy. Vinylnitrene 32 is stable in argon matrices but forms 2-cyanoindane-1,3-dione (3) upon further irradiation. Similarly, the irradiation of azide 1 in 2-methyltetrahydrofuran (MTHF) matrices at 5 K resulted in the ESR spectrum of vinylnitrene 32, which is stable up to at least 100 K. The zero-field splitting parameters for nitrene 32, D/hc = 0.7292 cm-1 and E/hc = 0.0048 cm-1, verify that it has significant 1,3-biradical character. Vinylnitrene 32 (λmax ~ 460 nm, τ = 22 μs) is also observed directly in solution at ambient temperature with laser flash photolysis of 1. Density functional theory (DFT) calculations support the characterization of vinylnitrene 32 and the proposed mechanism for its formation. Because vinylnitrene 32 is relatively stable, it has potential use as a building-block for high-spin assemblies.
- Sarkar, Sujan K.,Sawai, Asako,Kanahara, Kousei,Wentrup, Curt,Abe, Manabu,Gudmundsdottir, Anna D.
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- Electrophilic α-cyanation of 1,3-dicarbonyl compounds
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Electrophilic α-cyanation of activated methylene compounds was achieved under mild basic conditions using commercially available TsCN as a CN+ equivalent. A series of 1,3-dicarbonyl compounds, both cyclic and acyclic, were found to be suitable substrates for this transformation. Subjecting 1,1,1-trifluoro-1,3-dicarbonyl compounds to a modified procedure resulted in the formation of α-cyano ketones after trifluoroacetyl group fragmentation. An efficient one-pot cyanation/pyrazole formation sequence to 4-cyano pyrazoles from 1,3-diketones has also been developed. The Royal Society of Chemistry 2013.
- Akula, Ramulu,Xiong, Yan,Ibrahim, Hasim
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p. 10731 - 10735
(2013/09/02)
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- 2-Cyano indan-1,3-diones
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Pharmaceutical compositions are produced comprising as the active ingredient a compound of the formula STR1 or a pharmaceutically acceptable, nontoxic salt thereof or hydrate thereof, wherein R1, R2, R3 and R4 are each hydrogen, halogen, lower alkyl or lower alkoxy, or any two of the groups R1, R2, R3 and R4, taken together with the carbon atoms to which they are joined complete a substituted or unsubstituted carbocyclic ring, and X is a bond or an oxygen atom, is combined with a pharmaceutically acceptable, nontoxic inert diluent or carrier. Those compounds wherein R1, R2, R3 and R4 are not all simultaneously hydrogen are novel. When X is a bond, the compounds may be prepared by reacting an appropriately substituted 3-dyanomethylene phthalide with a base and, thereafter, if desired, converting the compound to a salt. When X is an oxygen atom, the compounds may be prepared by reacting a suitably substituted benzene derivative with an activated carbonyl group having a carbanion of the formula NC--CH--R, wherein R is a carboxylic acid ester group, and thereafter, if desired, converting the compound into a salt.
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