Synthesis of 5-substituted 2′-deoxyuridine-5′- phosphonate analogues and evaluation of their antiviral activity

Nucleosides, Nucleotides and Nucleic Acids

Volumn 31, Issue 3, 2012, Pages 256-272

  Van Poecke, Sara ^a   Sinnaeve, Davy ^a   Martins, José C ^a   Balzarini, Jan ^b   Van Calenbergh, Serge ^a  

^a GHENT UNIVERSITY   (Belgium)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

nucleosides; Antiviral activity; Antiviral nucleoside analogues; Phosphonates; Pyrimidine modification

Indexed keywords

1 [2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 (4 FLUOROPHENYL)URACIL; 1 [2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 (NAPHTHALEN 1 YL)URACIL; 1 [2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 (THIOPHEN 2 YL)URACIL; 1 [2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 PHENYLURACIL; 1 [2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL]URACIL; 1 [2,5,6 TRIDEOXY 6 (DIHYDROXYPHOSPHINYL) ALPHA DEXTRO HEXOFURANOSYL] 5 (4 FLUOROPHENYL)URACIL; 1 [2,5,6 TRIDEOXY 6 (DIHYDROXYPHOSPHINYL) ALPHA DEXTRO HEXOFURANOSYL] 5 (NAPHTHALEN 1 YL)URACIL; 1 [2,5,6 TRIDEOXY 6 (DIHYDROXYPHOSPHINYL) ALPHA DEXTRO HEXOFURANOSYL] 5 (THIOPHEN 2 YL)URACIL; 1 [2,5,6 TRIDEOXY 6 (DIHYDROXYPHOSPHINYL) ALPHA DEXTRO HEXOFURANOSYL] 5 PHENYLURACIL; 1 [2,5,6 TRIDEOXY 6 (DIHYDROXYPHOSPHINYL) ALPHA DEXTRO HEXOFURANOSYL]URACIL; 1 [2,5,6 TRIDEOXY 6 (DIHYDROXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 (4 FLUOROPHENYL)URACIL; 1 [2,5,6 TRIDEOXY 6 (DIHYDROXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 (NAPHTHALEN 1 YL)URACIL; 1 [2,5,6 TRIDEOXY 6 (DIHYDROXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 (THIOPHEN 2 YL)URACIL; 1 [2,5,6 TRIDEOXY 6 (DIHYDROXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 PHENYLURACIL; 1 [2,5,6 TRIDEOXY 6 (DIHYDROXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL]URACIL; 1 [3 O TERT BUTYLDIMETHYLSILYL 2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEX 5 ENOFURANOSYL]URACIL; 1 [3 O TERT BUTYLDIMETHYLSILYL 2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 (4 FLUOROPHENYL)URACIL; 1 [3 O TERT BUTYLDIMETHYLSILYL 2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 (NAPHTHALEN 1 YL)URACIL; 1 [3 O TERT BUTYLDIMETHYLSILYL 2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 (THIOPEN 2 YL)URACIL; 1 [3 O TERT BUTYLDIMETHYLSILYL 2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 BROMOURACIL; 1 [3 O TERT BUTYLDIMETHYLSILYL 2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL] 5 PHENYLURACIL; 1 [3 O TERT BUTYLDIMETHYLSILYL 2,5,6 TRIDEOXY 6 (DIETHOXYPHOSPHINYL) BETA DEXTRO HEXOFURANOSYL]URACIL; 5 (2 BROMOVINYL) 2' DEOXYURIDINE; ACICLOVIR; CIDOFOVIR; GANCICLOVIR; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANOMERIZATION; ANTIVIRAL ACTIVITY; ARTICLE; CELL GROWTH; CELL STRUCTURE; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYTOTOXICITY; DEPROTECTION REACTION; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; NONHUMAN; SUZUKI MIYAURA COUPLING; SUZUKI REACTION; VACCINIA VIRUS; VESICULAR STOMATITIS VIRUS; VIRUS STRAIN; WITTIG REACTION;

ANTIVIRAL AGENTS; MOLECULAR STRUCTURE; NUCLEOSIDES; ORGANOPHOSPHONATES;

EID: 84859718981     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2012.654876     Document Type: Article

References (11)

1. De Clercq, E.; Holý, A. Acyclic nucleoside phosphonates: A key class of antiviral drugs. Nat. Rev. Drug Discov. 2005, 4, 928-940. (Pubitemid 41637695)
2. Brulikova, L.; Hlavac, J. Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues. Beilstein J. Org. Chem. 2011, 7, 678-698.
3. Ivanov, A.V.; Simonyan, A.R.; Belanov, E.F.; Aleksandrova, L.A. Synthesis and antiviral activity of new 5-substituted 2′-deoxyuridine derivatives. Russ. J. Bioorg. Chem. 2005, 31, 556-562. (Pubitemid 41831016)
4. Wigerinck, P.; Kerremans, L.; Claes, P.; Snoeck, R.;Maudgal, P.; De Clercq, E.; Herdewijn, P. Synthesis and antiviral activity of 5-thien-2-yl-2′-deoxyuridine analogues. J. Med. Chem. 1993, 36, 538-543. (Pubitemid 23097418)
5. Sastry, J.K.; Nehete, P.N.; Khan, S.; Nowak, B.J.; Plunkett, W.; Arlinghaus, R.B.; Farquhar, D. Membrane-permeable dideoxyuridine 5′-monophosphate analog inhibits human-immunodeficiency- virus infection. Mol. Pharmacol. 1992, 41, 441-445.
6. Puech, F.; Gosselin, G.; Lefebvre, I.; Pompon, A.; Aubertin, A.M.; Kirn, A.; Imbach, J.L. Intracellular delivery of nucleoside monophosphates through a reductase-mediated activation process. Antiviral Res. 1993, 22, 155-174.
7. Fries, K.M.; Joswig, C.; Borch, R.F. Synthesis and biological evaluation of 5-fluoro-2′-deoxyuridine phosphoramidate analogs. J. Med. Chem. 1995, 38, 2672-3680.
8. Cosyn, L.; Van Calenbergh, S.; Joshi, B.V.; Ko, H.; Carter, R.L.; Harden, T.K.; Jacobson, K.A. Synthesis and P2Y receptor activity of nucleoside 5′-phosphonate derivatives. Bioorg. Med. Chem. Lett. 2009, 19, 3002-3005.
9. Rai, D.; Johar, M.; Srivastav, N.C.; Manning, T.; Agrawal, B.; Kunimoto, D.Y.; Kumar, R. Inhibition of Mycobacterium tuberculosis, Mycobacterium bovis, and Mycobacterium avium by novel dideoxy nucleosides. J. Med.Chem. 2007, 50, 4766-4774. (Pubitemid 47463249)
10. Pomeisl, K.; Holý, A.; Pohl, R. Pd-catalyzed Suzuki-Miyaura coupling reactions in the synthesis of 5- aryl-1-[2-(phosphonomethoxy)ethyl] uracils as potentialmultisubstrate inhibitors of thymidine phosphorylase. Tetrahedron Lett. 2007, 48, 3065-3067. (Pubitemid 46483595)
11. 3-protecting group. Tetrahedron Lett. 1991, 32, 1905-1908.