A facile synthesis of fluorophores based on 5-phenylethynyluracils

Synlett

Volumn , Issue 18, 2006, Pages 2997-3000

  Hudson, Robert H E ^a   Moszynski, Joanne M ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

5 phenylethynyluracil; Annulations; Furanouracils; Nucleobases; Silver(I) catalyzed cyclization

Indexed keywords

4 METHOXYPHENYLETHYNE; 4 NITROPHENYLFURANURACIL; 5 PHENYLETHYNYLURACIL; AGLYCONE; CYCLIC 6 (PHENYL)FURO[2,3 D]PYRIMIDIN 2(3H) ONE DERIVATIVE; OLIGONUCLEOTIDE; PEPTIDE NUCLEIC ACID; PHENYLACETYLENE; UNCLASSIFIED DRUG; URACIL;

ARTICLE; BASE PAIRING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLIZATION; FLUORESCENCE; QUANTITATIVE ANALYSIS; SYNTHESIS;

EID: 33751299823     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-948176     Document Type: Article

References (32)

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23. 6): 11.41 (s, 1 H), 11.17 (s, 1 H), 7.88 (s, 1 H).
24. 1H NMR: δ = 11.95 (s, 1 H), 8.32 (s, 1 H), 8.25 (d, 2 H, J = 8.9 Hz), 7.71 (d, 2 H, J = 8.8 Hz), 4.57 (s, 2 H), 4.17 (q, 2 H, J = 7.0 Hz), 1.21 (t, 3 H, J = 7.1 Hz).
25. 1H NMR: δ = 11.82 (s, 1 H), 8.20 (s, 1 H), 4.49 (s, 2H), 4.13 (q, 2 H, J = 7.1 Hz), 1.19 (t, 3 H, J = 7.1 Hz).
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29. 1H NMR: δ = 8.79 (s, 1 H), 8.34 (d, 2 H, J = 9.1 Hz), 8.08 (d, 2 H, J = 8.9 Hz), 7.69 (s, 1 H), 4.81 (s, 2H), 4.17 (q, 2 H, J = 7.1 Hz), 1.22 (t, 3 H, J = 7.1 Hz).
30. 6: 5a: 7.22; 5b: 7.04; 5c: 7.57; 6a: 7.37; 6b: 7.17; 6c: 7.69], disappearance of the resonance corresponding to the N3-imino proton (ca. 11.4-11.8 ppm) and a uniform downfield shift for the resonances associated with the phenyl ring and H6 of the uracil ring.
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32. 2 for 5 min and at a concentration of 2.5 μM. Although the N1-unsubstituted compounds (3a,b, 5a,b) are soluble in water, these were also examined in degassed MeOH at 2.5 μM for comparison purposes and the difficulty with fully deoxygenating the water. Fluorescence excitation and emission spectra were determined with at least 3 replicates with a 1 min rest between scans. For comparison of intensities, excitation was done at λ = 350 nm, and emission data from the maxima were used. At this time, we have no evidence for the occurrence of photochemistry during the course of these measurements. Extinction coefficients were determined for the wavelength of interest using at least three data points.