Synthesis, antiviral, and antitumor activity of 2-substituted purine methylenecyclopropane analogues of nucleosides

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 4, 2006, Pages 1247-1254

  Qin, Xinrong ^a   Chen, Xinchao ^a   Wang, Kun ^a   Polin, Lisa ^a   Kern, Earl R ^b   Drach, John C ^c   Gullen, Elizabeth ^d   Cheng, Yung Chi ^d   Zemlicka, Jiri ^a  

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

^b University of Alabama at Birmingham   (United States)

^c UNIVERSITY OF MICHIGAN   (United States)

^d YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antiviral and antitumor agents; Methylenecyclopropanes; Nucleoside analogues; Porcine liver esterase; Pronucleotides

Indexed keywords

2 FLUORO 9 [(2 HYDROXYMETHYL)CYCLOPROPYLIDENE]METHYLADENINE; 6 AMINO 2 CHLORO 9 [2 (HYDROXYMETHYL)CYCLOPROPYLIDENE]METHYLPURINE; 9 [2 (HYDROXYMETHYL)CYCLOPROPYLIDENE]METHYL]ISOGUANINE; [[(2 HYDROXYMETHYL)CYCLOPROPYLIDENE]METHYL]ISOGUANINE (METHYLPHENYLPHOSPHORYL) P N LEVO ALANINATE; ACICLOVIR; ANTIVIRUS AGENT; CYCLOPROPANE DERIVATIVE; ESTERASE; GANCICLOVIR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DAUDI CELL; DRUG EFFICACY; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENANTIOSELECTIVITY; EPSTEIN BARR VIRUS; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; MOUSE; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL LINE, TUMOR; CYCLOPROPANES; HUMANS; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR STRUCTURE; NUCLEOSIDES; NUCLEOTIDES; PURINES; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA; HUMAN HERPESVIRUS 4; HUMAN HERPESVIRUS 5; SUIDAE;

EID: 30344470782     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.09.052     Document Type: Article

References (29)

1. J. Zemlicka C.K. Chu Recent Advances in Nucleosides: Chemistry and Chemotherapy 2002 Elsevier Amsterdam 327
2. J. Zemlicka, and X. Chen R.F. Schinazi D.C. Liotta Frontiers in Nucleosides and Nucleic Acids 2004 IHL Press Tucker, Georgia 267
3. Y.-L. Qiu, R.G. Ptak, J.M. Breitenbach, J.-S. Lin, Y.-C. Cheng, J.C. Drach, E.R. Kern, and J. Zemlicka Antiviral Res. 43 1999 37
4. Y.-L. Qiu, F. Geiser, T. Kira, E. Gullen, Y.-C. Cheng, R.G. Ptak, J.M. Breitenbach, J.C. Drach, C.B. Hartline, E.R. Kern, and J. Zemlicka Antiviral Chem. Chemother. 11 2000 191
5. X. Chen, E.R. Kern, J.C. Drach, E. Gullen, Y.-C. Cheng, and J. Zemlicka J. Med. Chem. 46 2003 1531
6. 2-13 cited therein
7. R.P. Warrell Jr., and E. Berman J. Clin. Oncol. 4 1986 74
8. H.G. Chun, B.R. Leyland-Jones, and S.M. Caryk Cancer Treat. Rep. 70 1986 1225
9. R.J. Suhadolnik Nucleoside Antibiotics 1970 John Wiley and Sons New York pp 267-270
10. R.J. Suhadolnik Nucleosides as Biological Probes 1979 John Wiley and Sons New York pp 60-62
11. M.J. Lutz, J. Horlacher, and S.A. Benner Bioorg. Med. Chem. Lett. 8 1998 499
12. M.J. Robins, and B. Uznanski Can. J. Chem. 59 1981 2608
13. J. Davoll J. Am. Chem. Soc. 73 1951 3174
14. Y.-L. Qiu, R.G. Ptak, J.M. Breitenbach, J.-S. Lin, Y.-C. Cheng, E.R. Kern, J.C. Drach, and J. Zemlicka Antiviral Chem. Chemother. 9 1998 341
15. Y.-L. Qiu, and J. Zemlicka Synthesis 1998 1447
16. X. Chen, and J. Zemlicka J. Org. Chem. 67 2002 286
17. X. Chen, S. Matsumi, H. Mitsuya, and J. Zemlicka Nucleosides Nucleotides Nucleic Acids 22 2003 265
18. Y.-L. Qiu, M.B. Ksebati, R.G. Ptak, B.Y. Fan, J.M. Breitenbach, J.-S. Lin, Y.-C. Cheng, E.R. Kern, J.C. Drach, and J. Zemlicka J. Med. Chem. 41 1998 10
19. F. Seela, C. Wei, and Z. Kazimierczuk Hel. Chim. Acta 78 1995 1843
20. D. Cahard, C. McGuigan, and J. Balzarini Mini-Rev. Med. Chem. 4 2004 371
21. J. Zemlicka Biochim. Biophys. Acta 1587 2002 276
22. T.H. Corbett, F.A. Valeriote, L. Polin, C. Panchapor, S. Pugh, K. White, N. Lowichik, J. Knight, M.-C. Bissery, A. Wozniak, P. LoRusso, L. Biernat, D. Polin, J. Knight, S. Biggar, D. Looney, L. Demchik, J. Jones, L. Jones, S. Blair, K. Palmer, S. Essenmacher, L. Lisow, K.C. Mattes, P.F. Cavanaugh, J.B. Rake, and L. Baker F.A. Valeriote T.H. Corbett L.H. Baker Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery and Development 1992 Kluwer Academic Boston/Dordrecht/London 33
23. Hayashi, T.; Kumazawa, H.; Nishikawa, J. JP 2002088082.
24. Chem. Abstr. 136 2002 85821
25. G.B. Brown, and V.S. Weliky J. Org. Chem. 23 1958 125
26. This procedure was sufficient for a complete deacetylation.
27. N.L. Kushner, S.L. Williams, C.B. Hartline, E.A. Harden, D.J. Bidanset, X. Chen, J. Zemlicka, and E.R. Kern Nucleosides Nucleotides Nucleic Acids 22 2003 2105
28. J.-S. Lee, K. Paull, M. Alverez, C. Hose, A. Monks, A.T. Fojo, and S.E. Bates Mol. Pharmacol. 46 1994 627
29. T.H. Corbett, C. Panchapor, L. Polin, N. Lowichik, S. Pugh, K. White, J. Kushner, J. Meyer, J. Czarnecki, S. Chinnukroh, M. Edelstein, P. LoRusso, J.P. Horwitz, C. Grieshaber, R. Perni, M. Wentland, S. Coughlin, S. Elenbaas, R. Philion, and J. Rake Invest. New Drugs 17 1999 17