Phosphonate analogues of cyclopropavir phosphates and their E-isomers. Synthesis and antiviral activity

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 11, 2009, Pages 3892-3899

  Mhaske, Santosh B ^a   Ksebati, Bashar ^b   Prichard, Mark N ^c   Drach, John C ^d   Zemlicka, Jiri ^a  

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

^b WAYNE STATE UNIVERSITY   (United States)

^c UNIVERSITY OF ALABAMA SCHOOL OF MEDICINE   (United States)

^d UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Alkylation elimination; Antiviral agents; Cyclopropavir; Methylenecyclopropanes; Phosphonates; UL97 phosphotransferase

Indexed keywords

9 [[2 (HYDROXYMETHYL) 2 (2 PHOSPHONOETHYL)CYCLOPROPYLIDENE]METHYL]GUANINE; ANTIVIRUS AGENT; CYCLOPROPAVIR PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; EPSTEIN BARR VIRUS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; ISOMER; MOUSE; NONHUMAN; VARICELLA ZOSTER VIRUS; VIRUS CULTURE; VIRUS STRAIN;

ANIMALS; ANTIVIRAL AGENTS; CYCLOPROPANES; CYTOMEGALOVIRUS; GUANINE; HUMANS; INHIBITORY CONCENTRATION 50; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS; SIMPLEXVIRUS;

HUMAN HERPESVIRUS 2; HUMAN HERPESVIRUS 3; HUMAN HERPESVIRUS 4; MAIZE CHLOROTIC MOTTLE VIRUS; MURID HERPESVIRUS 1; SIMPLEXVIRUS;

EID: 65549158640     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.04.020     Document Type: Article

References (21)

1. Zemlicka J. In: De Clercq E. (Ed). Advances in Antiviral Drug Design (2007), Elsevier, Amsterdam 113-165
2. Zhou S., Kern E.R., Gullen E., Cheng Y.-C., Drach J.C., Matsumi S., Mitsuya H., and Zemlicka J. J. Med. Chem. 47 (2004) 6964
3. Zhou S., Kern E.R., Gullen E., Cheng Y.-C., Drach J.C., Tamiya S., Mitsuya H., and Zemlicka J. J. Med. Chem. 49 (2006) 6120
4. Zhou S., Breitenbach J.M., Borysko K.Z., Drach J.C., Kern E.R., Gullen E., Cheng Y.-C., and Zemlicka J. J. Med. Chem. 47 (2004) 566
5. Kern E.R., Kushner N.L., Hartline C.B., Williams-Azziz S.L., Harden E.A., Zhou S., Zemlicka J., and Prichard M.N. Antimicrob. Agents Chemother. 49 (2005) 1039
6. Kern E.R., Bidanset D.J., Hartline C.B., Yan Z., Zemlicka J., and Quenelle D.C. Antimicrob. Agents Chemother. 48 (2004) 4745
7. In: Martin J.C. (Ed). Nucleotide Analogues as Antiviral Agents. ACS Symposium Series 401 (1989), American Chemical Society, Washington, DC
8. Holy A. In: Chu C.K. (Ed). Recent Advances in Nucleosides: Chemistry and Chemotherapy (2002), Elsevier, Amsterdam 167-238
9. Prisbe E.J., Martin J.C., McGee D.P.C., Barker M.F., Smee D.F., Duke A.E., Matthews T.R., and Verheyden J.P.H. J. Med. Chem. 29 (1986) 671
10. Reist E.J., Sturm P.A., Pong R.Y., Tanga M.J., and Sidwell R.W. In: Martin J.C. (Ed). Nucleotide Analogues as Antiviral Agents. ACS Symposium Series 401 (1989), American Chemical Society, Washington, DC 17-34
11. Reist E.J., Bradford III W.W., Ruhland-Frisch B.L., Sturm P.A., Zaveri N.T., Huffman J., and Sidwell R.W. Nucleosides Nucleotides 13 (1994) 539
12. Huffman J.H., Sidwell R.W., Morrison A.G., Coombs J., and Reist E.J. Nucleosides Nucleotides 13 (1994) 607
13. Guan H.-P., Qiu Y.-L., Ksebati M.B., Kern E.R., and Zemlicka J. Tetrahedron 58 (2002) 6047
14. Yan Z., Kern E.R., Gullen E., Cheng Y.-C., Drach J.C., and Zemlicka J. J. Med. Chem. 48 (2005) 91
15. Li C., Prichard M.N., Korba B.E., Drach J.C., and Zemlicka J. Bioorg. Med. Chem. 16 (2008) 2148
16. Wagner A., Heitz M.-P., and Mioskowski C. Tetrahedron Lett. 30 (1989) 557
17. Bakos T., and Vincze I. Synth. Commun. 19 (1989) 523
18. 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., and Zemlicka J. J. Med. Chem. 41 (1998) 10
19. Breitenbach, J. M.; Borysko, K. Z.; Zemlicka, J.; Drach, J. C. 19th International Conference on Antiviral Research, San Juan, Puerto Rico; May 7-11, 2006, Abstract 61, Antiviral Res. 2006, 70, A69.
20. Borysko, K. Z.; Gentry, B. G.; Breitenbach, J. M.; Zemlicka, J.; Drach, J. C. 21st International Conference on Antiviral Research, Montreal, Quebec, Canada, April 13-17, 2008, Abstract 98, Antiviral Res. 2008, 78, A54.
21. Prichard M.N., Daily S.L., Jefferson G.M., Perry A.L., and Kern E.R. J. Virol. Methods 144 (2007) 86