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Original Articles

SYNTHESIS AND IN VITRO EVALUATION OF NOVEL ANTI-VARICELLA-ZOSTER VIRUS (VZV) NUCLEOSIDES

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Pages 653-656 | Published online: 07 Feb 2007

REFERENCES

  • McGuigan , C. , Yarnold , C. J. , Jones , G. , Velázquez , S. , Barucki , H. , Brancale , A. , Andrei , G. , Snoeck , R. , De Clercq , E. and Balzarini , J. 1999 . J. Med. Chem , 42 : 4479 – 4484 .
  • McGuigan , C. , Barucki , H. , Carangio , A. , Blewett , S. , Andrei , G. , Snoeck , R. , De Clercq , E. and Balzarini , J. 2000 . J. Med. Chem , submitted
  • Nyström , J. E. , McCanna , T. D. , Helquist , P. and Amouroux , R. 1988 . Synthesis , 1 : 56
  • Brancale , A. , Srinivasan , S. , McGuigan , C. , Andrei , G. , Snoeck , R. , De Clercq , E. and Balzarini , J. 2000 . Antiv. Chem & Chemother. , in press
  • 3[4-hydroxy-5-(hydroxymethyl)tetrahydrofuro-2-furanyl]-6-(3-p-methyl-phenoxypropyl)-2,3-dihydrofuro[2,3,d]pyrimidin-2-one (4g). 1H-nmr (d6-DMSO; 300 MHz): 9.00 (1H, s, H-4), 7.07 (2H, d, 3J = 7.9 Hz., m-Ph), 6.80 (2H, d, 3J = 7.9 Hz., o-Ph), 6.49 (1H, s, H-5), 6.17 (1H, dd, 3J = 5.6 Hz, H-1′), 5.30 (1H, d, 3J = 4.1 Hz, 3′-OH), 5.13 (1H, t, 3J = 4.9 Hz, 5′-OH), 4.23 (1H, m, H-3′), 3.98 (2H, t, 3J = 5.9, OCH2), 3.91 (1H, m, H-4′), 3.63 (2H, m, H-5′), 2.82 (2H, t, 3J = 6.9 Hz, α-CH2), 2.38 and 2.16 (2H, m, H-2′), 1.38 (2H, m, CH2). 13C-nmr (d6-DMSO; 75 MHz): 19.2 (CH3) 24.6, 26.65 (2 × CH2) 41.5 (C-2′), 61.1 (C-5′), 66.6 (OCH2), 70.0 (C-3′), 87.7 (C-4′), 88.4 (C-1′), 100.4 (C-5), 106.7 (C-4a), 114.6 (o-Ph), 129.5 (p-Ph), 130.1 (m-Ph), 137.2 (C-4), 154.1 (ipso-Ph), 156.7 (C-6), 157.9 (C-2), 171.5 (C-7a). MS (ES+) m/e 423 (MNa+, 100%), 307 (baseNa+, 10%). Accurate mass: C21H24N2O6Na requires: 423.1532. Found: 423.1534
  • De Clercq , E. , Holy , A , Rosenberg , I , Sakuma , T. , Balzarini , J. and Maudgal , P. C. 1986 . Nature , 324 : 464 – 467 .
  • McGuigan , C. , Brancale , A. , Barucki , H. , Srinivasan , S. , Jones , G. , Pathirana , R. , Blewett , S. , Alvarez , R. , Yarnold , C. J. , Carangio , A. , Velázquez , S. , Andrei , G. , De Clercq , E and Balzarini , J. 2000 . Drugs of the Future , : 25 in press

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