Synthesis, conformational analysis, and biological activity of a rigid carbocyclic analogue of 2′-deoxyaristeromycin built on a bicyclo[3.1.0]hexane template

Nucleosides and Nucleotides

Volumn 15, Issue 1-3, 1996, Pages 235-250

  Siddiqui, Maqbool A ^a   Ford Jr , Harry ^a   George, Clifford ^b   Marquez, Victor E ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HUMAN HERPESVIRUS 5;

2' DEOXYARISTEROMYCIN; ANTIVIRUS AGENT; CARBOCYCLIC 2' DEOXYARISTEROMYCIN; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOMEGALOVIRUS; DRUG SYNTHESIS; ENANTIOMER; EPSTEIN BARR VIRUS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0029923673     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319608002382     Document Type: Article

References (20)

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2. Marquez, V. E. Carbocyclic Nucleosides, in Advances in Antiviral Drug Design Vol. 2, De Clercq, E., Ed., Jai Press, Inc., Greenwich, Connecticut, USA (in press).
3. Saenger, W. Principles in Nucleic Acid Structure, Springer-Verlag, New York, 1984.
4. The commonly described shapes of ring puckering, such as 2′-exo/3′-endo, 2′-endo/3′-exo, and 2′-exo, correspond to a pentofuranose numbering system as described in the pseudorotational cycle: Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205.
5. Marquez, V. E.; Lim, B. B.; Barchi, Jr., J. J.; Nicklaus, M. C. Conformational Studies and Anti-HIV Activity of Mono- and Difluorodideoxy Nucleosides, in Nucleosides and Nucleotides as Antitumor and Antiviral Agents, Chu, C. K.; Baker, D. C., Eds., Plenum Press, New York, 1993, pp. 265-284.
6. Kishi, T.; Muroi, M.; Kusaka, T.; Nishikawa, M.; Kamiya, K.; Mizuno, K. Chem. Pharm. Bull. 1972, 20, 940.
7. Kalman, A.; Koritsanszky, T.; Beres, J.; Sagi, G. Nucleosides Nucleotides 1990, 9, 235.
8. Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi, Jr., J. J. Tetrahedron Lett. 1993, 34, 6233.
9. Altmann, K.-H.; Kesselring, R.; Francotte, E.; Rihs, G. Tetrahedron Lett. 1994, 35, 2331.
10. Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, Jr., J. J. J. Med. Chem. 1994, 37, 3389.
11. 2E) conformation (P = 342°) that is typical for the bicyclo[3.1.0]hexane system.
12. Marquez, V. E.; Lim, M.-I.; Tseng, C. K.-H.; Markovac, A.; Priest, M. A.; Khan, M. S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709.
13. Takano, S.; Ohkawa, T.; Ogasawara, K. Tetrahedron Lett. 1988, 29, 1823.
14. Mitsunobu, O. Synthesis 1981, 1.
15. Ring puckering is always described in reference to a pentofuranose system (see ref. 4). When referring to the ring pucker of carba-nucleosides - which may have a different numbering system - the reader should always translate it to a pentofuranose system. Because of this difference C2′ and C3′ in FIGURE 1 correspond, respectively, to C3′ and C2′ in a pentofuranose ring.
16. Shealy, Y. F.; O'Dell, C. A. Tetrahedron Lett. 1969, 2231.
17. Marumoto, R.; Yoshioka, Y.; Furukawa, Y.; Horyo M. Chem. Pharm. Bull. 1976, 24, 2624.
18. The antiviral testing was performed by Dr. Earl Kern of the University of Alabama at Birmingham and was supported by USPHS Contract N01-AI-35177 from the National Institute of Allergy and Infectious Diseases, NEH.
19. Borchardt, R. T. personal communication.
20. Wolfe, M. S.; Borchardt, R. T. J. Med. Chem. 1991, 34, 1521.