Spiropentane mimics of nucleosides: Analogues of 2'-deoxyadenosine and 2'-deoxyguanosine. Synthesis of all stereoisomers, isomeric assignment, and biological activity

Journal of Organic Chemistry

Volumn 65, Issue 5, 2000, Pages 1280-1290

  Guan, Hui Ping ^a   Ksebati, Mohamad B ^b   Cheng, Yung Chi ^c   Brach , John C ^d   Kern, Earl R ^b   Zemlicka, Jiri ^e  

^a WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b WAYNE STATE UNIVERSITY   (United States)

^c YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d UNIVERSITY OF MICHIGAN   (United States)

^e University of Alabama at Birmingham   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ADENOSINE DEAMINASE INHIBITOR; AMMONIA; CARBONYL DERIVATIVE; CYCLOPROPANE DERIVATIVE; DEOXYADENOSINE DERIVATIVE; DEOXYGUANOSINE DERIVATIVE; FORMIC ACID; NUCLEOSIDE ANALOG; PENTANE; RHODIUM; SPIRO COMPOUND; TERT BUTYL ALCOHOL;

ACETYLATION; ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DEBROMINATION; DRUG SYNTHESIS; EPSTEIN BARR VIRUS; HEPATITIS B VIRUS; HERPES SIMPLEX VIRUS 1; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROLYSIS; ISOMER; MOLECULAR MIMICRY; MOUSE; NONHUMAN; REACTION ANALYSIS; REDUCTION; STEREOISOMERISM; VARICELLA ZOSTER VIRUS; VIRUS INHIBITION;

ACETYLATION; ANTIVIRAL AGENTS; CYTOMEGALOVIRUS; DEOXYADENOSINES; DEOXYGUANOSINE; HERPESVIRUS 4, HUMAN; HUMANS; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; PENTANES; SPECTROPHOTOMETRY, INFRARED; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 0034629299     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991030r     Document Type: Article

References (36)

1. Nucleosides and Nucleotides as Antitumor and Antiviral Agents', Chu, C. K, Baker, D. C., Eds.), Plenum Press: New York, 1993.
2. Phadtare, S.; Zemlicka, J. J. Am. Chem. Soc. 1989, 111, 59255931.
3. Zemlicka, J. In ref 1, pp 73-100.
4. Zemlicka, J. Nucleosides Nucleotides 1997,16, 1003-1012.
5. Zhu, Y.-L.; Pai, S. B.; Liu, S.-H.; Grove, K. L.; Jones, B. C. N. M.; Simons, C.; Zemlicka, J.; Cheng, Y.-C. Antimicrob. Agents Chemother. 1997, 41, 1755- 1760.
6. 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.; Zemlicka, J. J. Med. Chem. 1998, 41, 10-23.
7. Qiu, Y.-L.; Ptak, R. G.; Breitenbach, J. M.; Lin, J.-S.; Cheng, Y.-C.; Kern, E. R.; Drach, J. C.; Zemlicka, J. Antiviral Chem. Chemother. 1998, 9, 341-352.
8. Qiu, Y.-L.; Hempel, A.; Camerman, N.; Camerman, A.; Geiser, F.; Ptak, R. G.; Breitenbach, J. M.; Kira, T.; Li, L.; Güllen, E.; Cheng, Y.-C.; Drach, J. C.; Zemlicka, J. J. Med. Chem. 1998, 41, 5257-5264.
9. Qiu, Y.-L.; Ksebati, M. B.; Zemlicka, J. Nudeosides Nudeotides in press.
10. Jones, B. C. N. M.; Drach, J. C.; Corbett, T. H.; Kessel, D.; Zemlicka, J. J. Org. Chem. 1995, 60, 6277-6280.
11. For the basis of this nomenclature see: Gajewski, J. J.; Burka, L. T. J. Org. Chem. 1970, 35, 2190-2196.
12. Lukin, K. A.; Zefirov, N. S. In The Chemistry of the Cydopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: New York, 1995; Vol. 2, pp 861-885.
13. Tserng, K.-Y.; Jin, S.-J.; Hoppel, C. L. Biochemistry 1991, 30, 10755-10760.
14. Li, D.; Zhou, H.-q.; Dakoji, S.; Shin, I.; Oh, E.; Liu, H.-w. J. Am. Chem. Soc. 1998, 720, 2008-2017.
15. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 5307-5310.
16. Cheng, C.; Shimo, T.; Somekawa, K.; Kawaminami, M. Tetrahedron Lett. 1997, 38, 9005-9008.
17. 4 in pentane led to a mixture of proximal and medial-anti spiropentanes (2:1) whereas reaction with an anti- isomer afforded medial-syn and distal spiropentanes (2:1).
18. Lai, M.-t.; Liu, L.-d.; Liu, H.-w. J. Am. Chem. Soc. 1991,113, 7388-7397.
19. Doyle, M. P.; Tamblyn, W. H.; Bagheri, V. J. Org. Chem. 1981, 46, 5094-5102.
20. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151-2157.
21. Agrofoglio, L. A.; Challand, S. R. Acyclic, Carbocyclic and L-Nucleosides; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1998; pp 182-183.
22. The use of 4,6-dichloro-5-nitropyrimidine for purine ring construction by a two-step procedure was reported: Coe, D. M.; Myers, P. L.; Parry, D. M.; Roberts, S. M.; Storer, R. J. Chem. Soc., Chem. Commun. 1990, 151-153.
23. Konzelman, L. M.; Conley, R. T. J. Org. Chem. 1968,33, 3828- 3838.
24. Eaton, P. E.; Shankar, B. K R.; Price, G. D.; Pluth, J. J.; Gilbert, E. E.; Alster, J.; Sandus, O. J. Org. Chem. 1984, 49, 185-186.
25. Norbeck, D. \V.; Sham, H. L.; Herrin, T.; Rosenbrook, W.; Plattner, J. J. J. Chem. Soc., Chem. Commun. 1992, 128-129.
26. Temple, C., Jr.; Smith, B. H.; Montgomery, J. A. J. Org. Chem. 1975, 40, 3141- 3142.
27. Friebolin, H. βasz'c One- and Two-Dimensional NMR Spectroscopy; VCH Publishers: New York, 1991; p 77.
28. Saenger, W. Principles of Nucleic Acid Structure; SpringerVerlag: New York, 1984; p 69.
29. Difficulty in pinpointing the "right" signal (presumably HS) from poorly resolved singlets of HS and II2 may account for lower NOE effects.
30. Winter, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1996, 39, 3300-3306.
31. Winter, H.; Maeda, Y.; Uchida, H.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1997, 40, 2191-2195.
32. Qiu, Y.-L.; Ptak, R. G.; Breitenbach, J. M.; Lin, J.-S.; Cheng, Y.-C.; Drach, J. C.; Kem, E. R.; Zeralicka, J. Antiviral Res. 1999, 43, 37-53.
33. Meier, C. Synlett 1998, 233-242.
34. McGuigan, C.; Tsang, H.-W.; Sutton, P. W.; De Clercq, E.; Balzarini, J. Antiviral Chem. Chemother. 1998, 9, 109-115.
35. Ben Cheikh, A.; Graine, L. E.; Recher, S. G.; Zemlicka, J. J. Org. Chem. 1988, 53, 929-936.
36. The product is a mixture of four diastereoisomers; see the 3IP NMR spectrum.