Cyclohexenyl nucleosides: Synthesis and biological activity of trans-3-(purin-9-yl)-4-cyclohexenylcarbinols

Tetrahedron

Volumn 52, Issue 27, 1996, Pages 8969-8978

  Konkel, Michael J ^a   Vince, Robert ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE; NUCLEOSIDE DERIVATIVE; PURINE DERIVATIVE; UNCLASSIFIED DRUG; [3 (6 CHLORO 9H PURIN 9 YL) 4 CYCLOHEXENYL]CARBINOL;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; HERPES SIMPLEX VIRUS 1; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; LEUKEMIA P 388; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY;

ANIMALIA; HERPES; HUMAN HERPESVIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0030200102     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00445-0     Document Type: Article

References (26)

1. 1. (a) Vince, R.; Hua, M.; Brownell, J.; Daluge, S.; Lee, F.; Shannon, W. M.; Lavelle, G. C; Quails, J.; Weislow, O. S.; Kiser, R.; Canonico, P. G.; Schultz, R. H.; Narayanan, V. L.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Biochem. Biophys. Res. Commun. 1988, 156, 1046-1053.
2. (b) Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17-21.
3. (c) Vince, R.; Kilama, J.; Pham, P. T.; Beers, S. A.; Bowden, B. J.; Keith, K. A.; Parker, W. B. Nucleosides Nucleotides 1995, 14, 1703-1708.
4. 2. Schaeffer, H. J.; Beauchamp, L.; de Miranda, P.; Elion, G. B.; Bauer, D. J.; Collins, P. Nature 1978, 272, 583-585.
5. 3. Hoshino, H.; Shimizu, N. J. Antibiot. 1987, 40, 1077-1078.
6. 4. (a) Verheggen, I.; Van Aerschot, A.; Toppet, S.; Snoeck, R.; Janssen, G.; Balzarini, J.; De Clercq, E.; Herdewijn, P. J. Med. Chem. 1993, 36, 2033-2040.
7. (b) Verheggen, I.; Van Aerschot, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; Claes, P.; De Clercq, E.; Herdewijn, P. J. Med. Chem. 1995, 38, 826-835.
8. (c) Pérez-Pérez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn, P. J. Org. Chem. 1995, 60, 1531-1537.
9. 5. (a) Schaeffer, H. J.; Weimar, R. D. J. Am. Chem. Soc. 1959, 81, 197-201.
10. (b) Young, R. C.; Jones, M.; Milliner, K. J.; Rana, K. K.; Ward, J. G. J. Med. Chem. 1990, 33, 2073-2080.
11. (c) Kitigawa, I.; Cha, B. C.; Nikae, T.; Okaichi, Y.; Takinama, Y.; Yoshikawa, M. Chem. Pharm. Bull. 1989, 37, 542-544.
12. (d) Ramesh, K.; Wolfe, M. S.; Lee, Y.; VanderVelde, D.; Borchardt, R. T. J. Org. Chem. 1992, 57, 5861-5868.
13. (e) Arango, J. H.; Geer, A.; Rodriguez, J.; Young, P. E.; Scheiner, P. Nucleosides Nucletides 1993, 12, 773-784.
14. 6. Konkel, M. J.; Vince, R. Nucleosides Nucleotides 1995, 14, 2061-2077.
15. 7. (a) Keinen, E.; Sahai, M.; Roth, Z.; Nudelman, A.; Herzig, J. J. Org. Chem. 1985, 50, 3558-3566.
16. (b) Murahashi, S.-I..; Taniguchi, Y.; Imada, Y.; and Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303.
17. 8. Mitsunobu, O. Synthesis 1981, 1-28.
18. 9. (a) Trost, B. M.; Kuo, G.-H; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621-622.
19. (b) Vince, R.; Peterson, M. L.; Lackey, J. W.; Mook, R. A.; Partridge, J. J. PCT Int. Appl., WO 91 15490, 1991 (Chem. Abstr. 1992, 116, 59910p).
20. (b) Vince, R.; Peterson, M. L.; Lackey, J. W.; Mook, R. A.; Partridge, J. J. PCT Int. Appl., WO 91 15490, 1991 (Chem. Abstr. 1992, 116, 59910p).
21. (c) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747.
22. (d) Coe, D. M.; Roberts, S. M.; Storer, R. J. Chem. Soc., Perkin Trans. 1 1992, 2695-2704.
23. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3378.
24. (f) Konkel, M. J.; Vince, R. Tetrahedron, 52, 1996, 799-808.
25. (g) Akella, L. B.; Vince, R. Tetrahedron, 52, 1996, 2789-2794.
26. 10. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191.