Subscribe to RSS
DOI: 10.1055/s-2004-829141
Synthesis and Biological Evaluation of Carbocyclic Nucleosides with 2′,3′-Dihomo-xylo-carbocyclic or Carbocyclic Fused to a Tetrahydrofuran Ring
Publication History
Publication Date:
13 July 2004 (online)
Abstract
New purinyl 2′,3′-dihomo-xylo-carbocyclic pentafuranosides and carbocyclic nucleosides fused with tetrahydrofuran ring were synthesized from (±)-c-4-amino-r-1,c-2,t-3-cyclopentanetrimethanol (8). The strongly acid medium in which the purine system was completed on pyrimidine derivative 9 caused condensation of the cis-hydroxymethyl groups, giving rise to a 3-oxabicyclo[3.3.0]octane structure. None of the new compounds exhibited more than very modest antiviral or antitumor activity.
Key words
xylo-carbocyclic nucleosides - tetrahydrofuran derivatives - synthesis - antiviral - antitumoral activity
- 1
De Clercq E. Clin. Microbiol. Rev. 1995, 200 - 2
Kolb VM. Prog. Drug Res. 1997, 48: 195 - 3
Colacino JM.Staschke KA. Prog. Drug Res. 1998, 50: 259 - 4
Zhu X.-F. Nucleosides, Nucleotides Nucleic Acids 2000, 19: 651 - 5
Marquez VE. Adv. Antiviral Drug Des. 1996, 2: 89 - 6
Agrofoglio L.SuhasFarese AE.Condom R.Challand SR.Earl A.Guedj R. Tetrahedron 1994, 50: 10611 - 7
Kishi T.Muroi M.Kusaka T.Nishikawa M.Kamiya K.Mizuno K. Chem. Pharm. Bull. 1972, 20: 940 - 8
Kishi T.Muroi M.Kusaka T.Nishikawa M.Kamiya K.Mizuno K. J. Chem. Soc. Chem. Commun. 1967, 852 - 9
Borchardt RT.Keller BT.Patel-Thombre U. J. Biol. Chem. 1984, 257: 4353 - 10
Vince R.Turakhia RH.Shannon WM.Arnett G. J. Med. Chem. 1987, 30: 2026 - 11
Vince R.Brownell J.Daluge S. J. Med. Chem. 1984, 27: 1358 - 12
Webb TR.Mitsuya H.Broder S. J. Med. Chem. 1988, 31: 1475 - 13
Yang CO.Kurz W.Engui EM.McRoberts MJ.Verheyden JPH.Kurz LJ.Walker KAM. Tetrahedron Lett. 1992, 33: 41 - 14
Kim MJ.Kim HO.Kim H.-D.Kim JH.Jeong LS.Chun MW. Bioorg. Med. Chem. Lett. 2003, 13: 3499 - 15
Shealy YF.Clayton JD. J. Am. Chem. Soc. 1969, 91: 3075 - 16
Daluge S.Vince R. J. Org. Chem. 1978, 43: 2311 - 17
Patil SD.Schneller SW.Hosoya M.Snoeck R.Andrei G.Balzarini J.De Clercq E. J. Med. Chem. 1992, 35: 3372 - 18
Patil SD.Scheneller SW.Hosoya M.Snoeck R.Andrei G.Balzarini J.De Clercq E. J. Med. Chem. 1992, 35: 3372 - 19
Caamaño O.Figueira MJ.Fernández F.García MD.Nieto MI.De Clercq E.Balzarini J. Nucleosides, Nucleotides Nucleic Acids 2001, 4-7: 1137 - 21
De Clercq E.Crommelin D.Couvreur P.Duchêne D. In In Vitro and Ex Vivo Test Systems to Rationalize Drug Design and Delivery Editions de Santé; Paris: 1994. p.108-125 - 22
De Clercq E.Descamps J.Verhelst G.Walter RT.Jones AS.Torrence PF.Shugar D. J. Infect. Dis. 1980, 141: 563 - 23
Figueira MJ.Caamaño O.Fernández F.García-Mera X.García MD. Tetrahedron 2002, 58: 967
References
The crystallographic data of 13 have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication No. CCDC 212937. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.