Constrained analogues of 2'-nor cyclic nucleoside monophosphates

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 11, 1997, Pages 1387-1392

  Tse, H L Allan ^a   Knight, David J ^b   Coates, Jonathan A V ^b,c   Mansour, Tarek S ^a  

^a Shire Canada   (Canada)

^b GLAXOSMITHKLINE   (United Kingdom)

^c Zenyth Therapeutics Limited Australia   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 OXATHIOLANE DERIVATIVE; CYCLIC NUCLEOTIDE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; HUMAN CYTOMEGALOVIRUS; NONHUMAN; REACTION ANALYSIS; VIRUS REPLICATION;

EID: 0030925529     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00245-X     Document Type: Article

References (10)

1. 2′-Nor-cGMP refers to the removal of the 2′CHOH moiety of 3′,5′-guanosine monophosphate DHPG-CP cyclic monophosphate of 9-(1,3-dihydroxy-2-propoxymethyl)guanine. This compound is related to 1′,2′-seco nucleosides. For a recent reference on 1′,2′-seco nucleosides see, Racha, S.; Vargeese, C.; Vemishetti, P.; El-Subbagh, H. I.; Abushanab, E.; Panzica, R. P. J. Med. Chem. 1996, 39, 1130.
2. Tolman, R. L.; Field, A. K.; Karkas, J. D.; Wagner, A. F.; Germershausen, J.; Crumpacker, C.; Scolnick, E. M. Biochem. Biophys. Res. Commun. 1985, 128, 1329.
3. Duke, A. E.; Smee, D. F.; Chernow, M.; Boehme, R.; Matthews, T. R. Antiviral Res. 1986, 6, 299.
4. Birnbaum, K. B.; Stolarski, R.; Shugard, D. Biochem. Biophys. Acta. 1994, 55, 1200.
5. 3 has been reported. For analogues with antiherpetic and anti-HIV activities in the ribofuranosyl and carbocyclic series respectively see Prisbe, E. J.; Maag, H.; Verheyden, J. P. H.; Rydzewski, R. M. In Nucleosides and Nucleotides an Antitumor and Antiviral Agents; Chu, C. K.; Baker, D. C.; Plennum: Press New York, 1993; pp 101-113; and Storer, R.; Baxter, A. D.; Boehme, R. E.; Clemens, I. R.; Hart, G. J.; Jones, M. F.; Marr, C. L. P.; Mason, A. M.; Mo, C-L.; Noble, S. A.; Paternoster, I. L.; Robertson, C.; Ryan, D. M.; Sowa, M. A.; Weir, N. G.; Williamson, C. In Recent Advances in the Chemistry of Anti-Infective Agents; Bentley, P. H.; Ponsford, R., Eds.; Royal Society of Chemistry: Cambridge, 1993; pp 251-265.
6. 3 has been reported. For analogues with antiherpetic and anti-HIV activities in the ribofuranosyl and carbocyclic series respectively see Prisbe, E. J.; Maag, H.; Verheyden, J. P. H.; Rydzewski, R. M. In Nucleosides and Nucleotides an Antitumor and Antiviral Agents; Chu, C. K.; Baker, D. C.; Plennum: Press New York, 1993; pp 101-113; and Storer, R.; Baxter, A. D.; Boehme, R. E.; Clemens, I. R.; Hart, G. J.; Jones, M. F.; Marr, C. L. P.; Mason, A. M.; Mo, C-L.; Noble, S. A.; Paternoster, I. L.; Robertson, C.; Ryan, D. M.; Sowa, M. A.; Weir, N. G.; Williamson, C. In Recent Advances in the Chemistry of Anti-Infective Agents; Bentley, P. H.; Ponsford, R., Eds.; Royal Society of Chemistry: Cambridge, 1993; pp 251-265.
7. For a recent review see: Naesens, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; Neyts, J.; De Clercq, E. Antiviral. Chem. Chemother. 1997, 8, 1.
8. Zou, R.; Robins, M. J. Can. J. Chem. 1987, 65, 1436.
9. 50 was assessed on virus-free cell layers. Visual assessment of the integrity of the treated monolayers at each compound dose was made.
10. 6) δ 34.67, 71.21 (d, J= 5.7 Hz), 72.21 (d, J= 5.6 Hz), 86.94, 87.42 (d, J= 5.7 Hz), 72.21 (d, J= 5.6 Hz), 86.94, 87.42 (d, J= 5.1 Hz), 87.55, 141.95, 153.52, 162.30.