116
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

Fluoroanalogues of Anti-Cytomegalovirus Agent Cyclopropavir: Synthesis and Antiviral Activity of (E)- and (Z)-9-{[2,2-Bis(Hydroxymethyl)-3-Fluorocyclopropylidene]Methyl}-Adenines and Guanines

, , &
Pages 231-243 | Received 14 Jul 2006, Accepted 03 Nov 2006, Published online: 04 Apr 2007

REFERENCES AND NOTES

  • Zemlicka , J. 2002 . “ Unusual analogues of nucleosides: chemistry and biological activity ” . In Recent Advances in Nucleosides: Chemistry and Chemotherapy , Edited by: Chu , C.K. 327 – 357 . Amsterdam : Elsevier .
  • Zemlicka , J. and Chen , X. 2004 . “ Methylenecyclopropane analogs of nucleosides as antiviral agents ” . In Frontiers in Nucleosides and Nucleic Acids , Edited by: Schinazi , R.F. and Liotta , D.C. 267 – 307 . Tucker , Georgia : IHL Press .
  • Zhou , S. , Breitenbach , J.M. , Borysko , K.Z. , Drach , J.C. , Kern , E.R. , Gullen , E. , Cheng , Y.-C. and Zemlicka , J. 2004 . Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]- methylpurines and -pyrimidines: Second-generation methylenecyclopropane analogues of nucleosides . J. Med. Chem. , 47 : 566 – 575 .
  • Kern , E.R. , Bidanset , D.J. , Hartline , C.B. , Yan , Z. , Zemlicka , J. and Quenelle , D.C. 2004 . Oral activity of a methylenecyclopropane analog, cyclopropavir, in animal models for cytomegalovirus infections . Antimicrob. Agents Chemother. , 48 : 4745 – 4753 .
  • Yan , Z. , Kern , E. R. , Gullen , E. , Cheng , Y.-C. , Drach , J.C. and Zemlicka , J. 2005 . Nucleotides and pronucleotides of 2,2-bis(hydroxymethyl)cyclopropane analogues of purine nucleosides: Synthesis and antiviral activity . J. Med. Chem. , 48 : 91 – 99 .
  • Kern , E.R. , Kushner , N.L. , Hartline , C.B. , Williams-Azziz , S.L. , Harden , E.A. , Zhou , S. , Zemlicka , J. and Prichard , M.N. 2005 . In vitro activity and mechanism of action of methylenecyclopropane analogs of nucleosides against herpesvirus replication . Antimicrob. Agents Chemother. , 49 : 1039 – 1045 .
  • Drach , J.C. , Breitenbach , J.M. , Borysko , K.Z. , Komazin , G. , Yan , Z. and Zemlicka , J. 2005 . Mechanism of action against human cytomegalovirus of first and second generation methylenecyclopropane purines . Antiviral Res. , 65 : A75
  • Breitenbach , J.M. , Borysko , K.Z. , Zemlicka , J. and Drach , J.C. 2006 . Resistance of human cytomegalovirus with single and double mutations in UL97 to first and second generation of methylenecyclopropane purines . Antiviral Res. , 70 : A69
  • Wang , R. , Ksebati , M.B. , Corbett , T.H. , Kern , E.R. , Drach , J.C. and Zemlicka , J. 2001 . Methylene-gem-difluorocyclopropane analogues of nucleosides: Synthesis, cyclopropene-methylenecyclopropane rearrangement, and biological activity . J. Med. Chem. , 44 : 4019 – 4022 .
  • Zhou , S. , Kern , E.R. , Gullen , E. , Cheng , Y.-C. , Drach , J.C. , Matsumi , S. , Mitsuya , H. and Zemlicka , J. 2004 . (Z)- and (E)-[2-fluoro-(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines, a new class of methylenecyclopropane analogues of nucleosides: synthesis and antiviral activity . J. Med. Chem. , 47 : 6964 – 6972 .
  • Zemlicka , J. , Zhou , S. , Kern , E. , Drach , J.C. and Mitsuya , H. 2006 . Synthesis and antiviral activity of methylene-3-fluorocyclopropane analogues . Antiviral Res. , 70 : A68
  • Zhou , S. , Kern , E.R. , Gullen , E. , Cheng , Y.-C. , Drach , J.C. , Tamiya , S. , Mitsuya , H. and Zemlicka , J. 2006 . 9-{[3-Fluoro-2-(hydroxymethyl)cyclopropylidene]methyl}adenines and guanines. Synthesis and antiviral activity of all stereoisomers . J. Med. Chem. , 49 : 6120 – 6128 .
  • Csuk , R. and Thiede , G. 2003 . Synthese monofluorierter cyclopropanoider Nucleosidanaloga . Z. Naturforsch. , 58b : 97 – 105 .
  • Schlosser , M. and Heinz , G. 1971 . Fluoroorganische synthesen, III. Monofluorocarben . Chem. Ber. , 104 : 1934 – 1941 .
  • Reich , H.J. , Cohen , M.L. and Clark , P.S. 1988 . Reagents for synthesis of organoselenium compounds: Diphenyl diselenide and benzeneselenenyl chloride . Org. Syn. , Vol. VI : 533 – 537 . Coll.
  • Sharpless , B.K. and Young , M.W. 1975 . Olefin synthesis. Rate enhancement of the elimination of alkyl aryl selenoxides by electron-withdrawing substituents . J. Org. Chem. , 40 : 947 – 949 .
  • Numbering according to Ref.;[13] cis, trans relationship refers to TBDMSOCH2 and Br.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.