1967

DOI: 10.1021/jm00313a010

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Nucleosides. XXXVII. 5,6-Substituted 5-Fluorodihydropyrimidines and Their 2′-Deoxyribonucleosides

Robert Duschinsky¹,

Tobias Gabriel²,

William Tautz³

et al.

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Df = Bk[lo][h'][br-]1

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1974

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Cited by 51 publications

(32 citation statements)

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“…The composition of the fluorohydrin 5 products, as determined by NMR, was consistent with that described by Visser 28. Our attempts to substitute the sublimation procedure with certain other types of hydrolysis and elimination previously described in literature,29–31 as well as using microwave irradiation, did not result in sufficient conversion of the fluorohydrin 5 to the target compound 1 or any advantages for purification.…”

Section: Resultssupporting

confidence: 82%

Synthesis and purification of [2‐¹³C]‐5‐fluorouracil

¹

,

²

,

³

2011

Labelled Comp Radiopharmac

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a,bÃ [2-13 C]-5-Fluoropyrimidine-2,4(1H,3H)-dione ([2-13 C]-5-fluorouracil or [2-13 C]-5-FU) is a potential diagnostic agent for measuring 5-FU-induced toxicity in cancer patients. It was prepared and purified with isotopic and chemical purity of499% on a multigram scale in a two-step synthesis from [13 C]-urea. Preparative separation of [2-13 C]-FU and [2-13 C]-uracil was carried out by automated medium pressure silica gel column chromatography. The method is applicable to a broader range of 5-FU isotopic analogs derived from labeled uracil.

“…The composition of the fluorohydrin 5 products, as determined by NMR, was consistent with that described by Visser 28. Our attempts to substitute the sublimation procedure with certain other types of hydrolysis and elimination previously described in literature,29–31 as well as using microwave irradiation, did not result in sufficient conversion of the fluorohydrin 5 to the target compound 1 or any advantages for purification.…”

Section: Resultssupporting

confidence: 82%

Synthesis and purification of [2‐¹³C]‐5‐fluorouracil

¹

,

²

,

³

2011

Labelled Comp Radiopharmac

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a,bÃ [2-13 C]-5-Fluoropyrimidine-2,4(1H,3H)-dione ([2-13 C]-5-fluorouracil or [2-13 C]-5-FU) is a potential diagnostic agent for measuring 5-FU-induced toxicity in cancer patients. It was prepared and purified with isotopic and chemical purity of499% on a multigram scale in a two-step synthesis from [13 C]-urea. Preparative separation of [2-13 C]-FU and [2-13 C]-uracil was carried out by automated medium pressure silica gel column chromatography. The method is applicable to a broader range of 5-FU isotopic analogs derived from labeled uracil.

“…Dus-chinsky, et al, 23 In conclusion we point out the similarities between the debromination reactions of 10 and 14 and the dehydration process 23 -25. Dus-chinsky, et al, 23 In conclusion we point out the similarities between the debromination reactions of 10 and 14 and the dehydration process 23 -25.…”

Section: Df = Bk[lo][h'][br-]supporting

confidence: 57%

Bromide ion induced debromination of the 5,5-dibromo derivatives of 4,6-dihydroxy pyrimidine and 6-methyluracil

Tee²

1974

J. Org. Chem.

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In aqueous solutions "4,6-dihydroxypyrimidine" and 6-methyluracil undergo rapid reaction with 2 molar equiv of bromine, to yield firstly their corresponding 5-bromo compounds, and secondly their 5,5-dibromo derivatives. Under acidic conditions, these latter compounds are acted upon by bromide ion to yield their monobromo derivatives and bromine. The liberated bromine is consumed in the presence of unreacted substrate to give a second equivalent of the 5-bromopyrimidinedione. The kinetics of debromination have been measured, and probable mechanisms for these processes are discussed with reference to previous studies on the dehalogenation of similar derivatives.In an earlier study' we concluded that in aqueous sulfuric acid solutions the bromination at the 5 position of 2pyrimidinone (1) proceeds by an addition-elimination mechanism 1 -2 -3, in which acid-catalyzed deprotonation of the 5 position of 2 is the rate-determining step.l Similar mechanisms appear to be operative in the bromination of other pyrimidines bearing oxo and/or amino substituents a t the 2 and/or 4 positions.2 For example, 1,3-dimethyluracil (4) adds "HOBr" to yield the adduct 5,2-4 which subsequently rearomatizes to the 5-bromouracil 6 by a slow acid-catalyzed dehydration.2 In the presence of bromine 5-bromo-1,3-dimethyluracil (6) forms the 5,5-dibromo derivative 7. 1 2 3 4 5 6 7We now find that, in an analogous manner, 6-methyluracil ( 1 1) reacts rapidly with bromine to give, successively, 12, 13, and 14 (Scheme I).5 Similarly, the reaction of "4,6-dihydroxypyrimidine" (8) with bromine yields a 5,5-dibromo derivative 10 oia the 5-bromopyrimidine 9 (see Scheme 11). We attempted to follow the kinetics of the brominations 8 -9 -10, but obtained curious results. Subsequent experimentation revealed that these processes occur very rapidly, and that in fact the reaction we were following was the reverse reaction 10 -9. Similar behavior was exhibited by 6-methyluracil ( l l ) , and in this paper we report a kinetic study of the debrominations 10 -9 and 14 -13. Results and DiscussionAlthough the major tautomeric component of "4,6-dihydroxypyrimidine" (8) in aqueous solutions is not known with certainty,6 a pmr study in DMSO-deID20 solutions Scheme I 0 0 0 Br 0 Br Me H 19 14 Scheme I1 0 0 0 Br HO" H X T HO bH + ':YjH 1 -Hi 8a 8 b 0 0 HO N 9a 9b

“…This first group of ana logues has been synthesized by fitting to thymidine a method described for 5-fluorodeoxyuridine [5]. The diastereoisomers1 were separated by thin-layer chromatogra phy (vide infra) thanks to recent solvents systems that one of us has recently de scribed [3].…”

Section: Methodsmentioning

confidence: 99%

Inhibition of Ehrlich’s Ascites Cells Thymidine Kinase by a New Class of Nucleosides Derivatives

1974

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Two classes of 5,6-dihydrothymidine derivatives have been synthesized, i.e., trans-6-alkoxy-5-bromo-5,6-dihydrothymidine and trans-6-alkoyloxy-5-bromo-5,6-dihydrothymidine. They have shown to be competitive inhibitors of thymidine kinase of Ehrlich’s ascites cells at low concentrations (10^-4 m) with respect to thymidine. The (+) and (-) diastereoisomeric forms did not show any difference in their biological activities.

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