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Original Articles

SYNTHESIS AND ANTIVIRAL ACTIVITY OF NOVEL EXOMETHYLENE CYCLOPROPYL NUCLEOSIDES

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Pages 1059-1062 | Published online: 07 Feb 2007

REFERENCES

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  • Agrofoglio , L. A. and Challand , S. R. 1998 . Acyclic, Carbocyclic and L-Nucleosides Dordrecht : Kluwer Academic Publisher .
  • Elion , G. B. , Furman , P. A. , Fyfe , J. A. , de Miranda , P. , Beauchamp , L. and Schaeffer , H. J. 1977 . Proc. Natl. Acad. Sci. USA , 74 : 5716
  • Martin , J. C. , Dvorak , C. A. , Smee , D. F. , Matthews , T. R. , Julien , P. H. and Verheyden , J. P.H. 1983 . J. Med. Chem. , 26 : 759
  • Qiu , Y.-L. , Ksebati , M. B. , Ptak , R. G. , Fan , B. Y. , Breitenbach , J. M. , Lin , J.-S. , Cheng , Y.-C. , Kern , E. R. , Drach , J. C. and Zemlicka , J. 1998 . J. Med. Chem. , 41 : 10
  • Qiu , Y.-L. , Hempel , A. , Camerman , N. , Camerman , A. , Geiser , F. , Ptak , R. G. , Brietenbach , J. M. , Kira , T. , Li. , L. , Gullen , E. , Cheng , Y.-C. , Drach , J. C. and Zemlicka , J. 1998 . J. Med. Chem. , 41 : 5257
  • Sekiyama , T. , Hatsuya , S. , Tanaka , Y. , Uchiyama , M. , Ono , N. , Iwayama , S. , Oikawa , M. , Suzuki , K. , Okunishi , M. and Tsuji , T. 1998 . J. Med. Chem. , 41 : 1284
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  • Compound 9: white solid; m. p. 198–199°C; IR (KBr) cm−1 : 3274–3162 (OH, NH2); UV (MeOH) λmax 262 (ϵ 8700); 1H-NMR (300 MHz, DMSO-d6) δ 8.19, 8.14 (each 1H, s, C2-H, C8-H), 7.17 (2H, s, NH 2), 5.46 (1H, s, CH 2˭C), 5.38 (1H, s, CH 2˭C), 4.70 (1H, t, J = 5.5 Hz, OH), 4.24 (1H, dd, J = 6, 14.0 Hz, CH 2N), 4.03 (1H, dd, J = 7.6, 14.0 Hz, CH 2N), 3.44, 3.17 (each 1H, m, CH 2O), 1.80 (2H, m, 2 × cyPr CH)
  • Compound 10: white solid; m. p. 96–98°C; IR (KBr) cm−1 : 3312 (OH) : UV (MeOH)λmax 264 (ϵ 7400); 1H NMR (300 MHz, DMSO-d6) δ 8.80, 8.87 (each 1H, s, C2-H, C8-H), 5.48, 5.41 (each 1H, s, CH 2˭C), 4.68 (1H, t, J = 5.55 Hz, OH), 4.46 (1H, dd, J = 5.8, 14.2 Hz, CH 2N), 4.16 (1H, dd, J = 8.2, 14.2 Hz, CH 2N), 3.49, 3.11 (each 1H, m, CH 2O), 1.86(2H, m, 2 × cyPr CH)
  • Compound 11: white solid; m. p. 212–213°C; IR (KBr) cm−1 : 3371 (OH), 1677 (lactam C˭O); UV (MeOH) λmax 250 (ϵ 19200); 1H NMR (300 MHz, DMSO-d6) δ 12.26 (1H, bs, C6-OH), 8.14, 8.03 (each 1H, s, C2-H, C8-H), 5.46, 5.38 (each 1H, s, CH 2˭C), 4.70(1H, t, J = 5.4 Hz, CH2OH), 4.24(1H, dd, J = 5.6, 14.2 Hz, CH 2N), 4.03 (1H, dd, J = 7.8, 14.2 Hz, CH 2N), 3.46 (1H, m, CH 2O), 3.16 (1H, m, CH 2O), 1.79 (2H, m, 2 × cyPr CH)
  • Compound 12: white solid; m. p. 183–185°C; IR (KBr) cm−1 : 3326–3221 (OH, NH2); UV (MeOH) λmax 310 (ϵ 11900); 1H NMR (300 MHz, DMSO-d6) δ 8.28 (1H, s, C8-H), 6.89 (2H, bs, NH2), 5.47, 5.40 (each 1H, s, CH 2˭C), 4.69 (1H, t, J = 5.4 Hz, OH), 4.17 (1H, dd, J = 5.8, 14.2 Hz, CH 2N), 3.92 (1H, dd, J = 7.9, 14.2 Hz, CH 2N), 3.47, 3.14(each 1H, m, CH 2O), 1.79 (2H, m, 2 × cyPr CH)
  • Compound 13: white solid. m. p. 257°C; IR (KBr) cm−1 : 3150–174 (OH, lactam NH, NH2), 1687 (lactam C˭O) : UV (MeOH) λmax 254 (ϵ 8500).1H NMR (300 MHz, DMSO-d6) δ 10.56 (1H, bs, C6-OH), 7.73 (1H, s, C8-H), 6.43 (2H, bs, NH 2), 5.46, 5.39 (each 1H, s, CH 2˭C), 4.7(1H, t, J = 5.5, OH), 4.01 (1H, dd, J = 5.7, 14.2 Hz, CH 2N), 3.84 (1H, dd, J = 7.6, 14.2 Hz, CH 2N), 3.44, 3.18 (each 1H, m, CH 2O), 1.75, 1.73 (each 1H, m, cyPr CH)
  • Compound 14: white solid; m. p. 209–210°C; IR (KBr) cm−1 : 3457–3170 (OH, NH2); UV (MeOH) λmax 256 (ϵ 7100), 282 (ϵ 8800); 1H NMR (300 MHz, DMSO-d6) δ 7.75 (1H, s, C8-H), 6.62, 5.75 (each 2H, bs, 2 × NH 2), 5.46, 5.39 (each 1H, s, CH 2˭C), 4.7 (1H, t, J = 5.5, OH), 4.02 (1H, dd, J = 6.0,14.1 Hz, CH 2N), 3.85 (1H, dd, J = 7.5, 14.1 Hz, CH 2N), 3.43, 3.19 (each 1H, m, CH 2O), 1.75 (2H, m, 2 × cyPr CH)

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