5′-Noraristeromycin derivatives isomeric to aristeromycin and 2′-deoxyaristeromycin

Tetrahedron

Volumn 61, Issue 7, 2005, Pages 1839-1843

  Yin, Xue Qiang ^a   Schneller, Stewart W ^a  

^a AUBURN UNIVERSITY   (United States)

Author keywords

3 Homo carbocylic nucleosides; Epoxide ring opening; Mitsunobu reaction

Indexed keywords

4 (6 AMINOPURIN 9 YL) 2 (HYDROXYMETHYL)CYCLOPENTANOL; 4 (6 AMINOPURIN 9 YL) 2 HYDROXYMETHYLCYCLOPENTANE 1,3 DIOL; ADENINE DERIVATIVE; ANTIVIRUS AGENT; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CYTOTOXICITY; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; EPSTEIN BARR VIRUS; HUMAN; HUMAN CELL; ISOMERISM; NONHUMAN; PRIORITY JOURNAL; STATISTICAL SIGNIFICANCE;

HOMO; HUMAN HERPESVIRUS 4;

EID: 12944320845     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.12.016     Document Type: Article

References (26)

1. V.E. Marquez Advan. Antiviral Drug Design 2 1996 89 146
2. For leading references on oligomers possessing carbacyclic monomers see Ref. 1 and Y. Xu, K. Kino, and H. Sugiyama J. Biomol. Struct. Dyn. 20 2002 437 446
3. L. Agrofoglio, E. Suhas, A. Farese, R. Condom, S.R. Challand, R.A. Earl, and R. Guedj Tetrahedron 50 1994 10611 10670
4. J. Wengel Org. Biomol. Chem. 2 2004 277 280
5. For a leading reference, see V.P. Rajappan, S.W. Schneller, S.L. Williams, and E.R. Kern Bioorg. Med. Chem. 10 2002 883 886
6. M. Koga, K. Abe, S. Ozaki, and S.W. Schneller Nucleic Acids Symp. Ser. 1994 65 66
7. K. Laumen, E.H. Reimerdes, and M. Schneider Tetrahedron Lett. 26 1985 407 410
8. K. Laumen, and M. Schneider Tetrahedron Lett. 25 1984 5875 5878
9. K.L. Seley, S.W. Schneller, D. Rattendi, and C.J. Bacchi J. Med. Chem. 40 1997 622 624
10. M. Matsuumi, M. Ito, and Y. Kobayashi Synlett 2002 1508 1510
11. H.B. Henbest, and R.A.L. Wilson J. Chem. Soc. 1957 1958 1965
12. This result is consistent with related cyclopentyl epoxide ring openings using adenine and thymine reported by (a) G.V.B. Madhavan, D.P.C. McGee, R.M. Rydzewski, R. Boehme, J.C. Martin, and E.J. Prisbe J. Med. Chem. 31 1988 1798 1804
13. K. Biggadike, A.D. Borthwick, and A.M. Exall J. Chem. Soc., Chem. Commun. 1990 458 459
14. (c) Cyrstallographic data (excluding structure factors) for 8 have been deposited with Cambridge Crystallographic Data Centre as supplementary number CCDC 253434.
15. A.D. Borthwick, A.J. Crame, A.M. Exall, and G.G. Weingarten Tetrahedron Lett. 35 1994 7677 7680
16. J.P. Marino, R. Fernández, R. de la Pradilla, and E. Laborde J. Org. Chem. 52 1987 4898 4913
17. 14
18. (b) Derivative 3 was only assayed against the herpes viruses.
19. For leading references on the procedures used for the assays see (a) Ref. 5.
20. S.M. Siddiqi, X. Chen, S.W. Schneller, S. Ikeda, R. Snoeck, G. Andrei, J. Balzarini, and E. de Clercq J. Med. Chem. 37 1994 551 554
21. K.L. Seley, S.W. Schneller, and B. Korba Nucleosides Nucleotides 16 1997 2095 2099
22. (d) http://www.usu.edu/iar/Brochure/brochure.html (October 14, 2004).
23. Confirmation of 10 as the regioisomeric form shown in Scheme 1 was achieved by its conversion to 2 whose structure was related to the X-ray analysis of 8.
24. 17 to produce 14, a structure assigned by NMR analysis (see text).
25. Inversion of configuration in the Mitsunobu reaction is well documented (a) O. Mitsunobu Synthesis 1981 1 28
26. D.L. Hughes Org. Prep. Proc. Int. 28 1996 127 164