Synthesis and anti-HIV evaluation of new acyclic phosphonate nucleotide analogues and their bis(SATE) derivatives

Nucleosides, Nucleotides and Nucleic Acids

Volumn 29, Issue 8, 2010, Pages 581-590

  Li, Hua ^a   Hong, Joon Hee ^a  

^a Chosun University   (South Korea)

Author keywords

Antiviral agent; phosphonate nucleoside; SATE prodrug

Indexed keywords

ADENINE DERIVATIVE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BIS(S ACYL 2 THIOETHYL); CYTOSINE DERIVATIVE; DIETHYLMALONATE; MALONIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PH MEASUREMENT;

ACIDS, ACYCLIC; ANTI-HIV AGENTS; HIV-1; HYDROGEN-ION CONCENTRATION; MALONATES; MOLECULAR STRUCTURE; NUCLEOSIDES; PHOSPHONIC ACIDS; PRODRUGS;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 77954888706     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2010.495958     Document Type: Article

References (16)

1. El Ashry, E.S.H.; El Kilany, Y. Acyclonucleosides: part 1,2,3 in Advances in Heterocyclic Chemisty, Academic Press, 1997, vols. 67, 68, 69.
2. De Clercq, E. Broad-spectrum anti-DNA virus and anti-retrovirus activity of phosphonylmethoxyalkylpurines and pyrimidines. Biochem. Pharmacol. 1991, 42, 963-972.
3. Pauwels, R.; Balzarini, J.; Schols, D.; Baba, M.; Desmyter, J.; Rosenberg, I.; Holy, A.; De Clercq, E. Phosphonylmethoxyethyl purine derivatives, a new class of anti-human immunodeficiency virus agents. Antimicrob. Agents Chemother. 1988, 32, 1025-1030.
4. De Clercq, E. Potential of acyclic nucleoside phosphonates in the treatment of DNA virus and retrovirus infections. Expert. Rev. Anti. Infect. Ther. 2003, 1, 21-43.
5. Jones, R., J. Bischofberger, N. Minireview: Nucleotide prodrugs. Antiviral Res., 1995, 27, 1-17.
6. Srinivas, R.V.; Robbins, B.L.; Connelly, M.C.; Gong, Y.F.; Bischofberger, N.; Fridland, A. Metabolism and in vitro antiretroviral activities of bis(pivaloyloxymethyl) prodrugs of acyclic nucleoside phosphonates. Antimicrob. Agents Chemother. 1993, 37, 2247-2250.
7. Benzaria, S.; Ṕelicano, H.; Johnson, R.; Maury, G.; Imbach, J.L.; Aubertin, A.M.; Obert, G.; Gosselin,G. Synthesis, in vitro antiviral evaluation, and stability studies of bis(S-acyl-2-thioethyl) ester derivatives of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) as potential PMEA prodrugs with improved oral bioavailability. J. Med. Chem. 1996, 39, 4958-4965.
8. Paĺu, G.; Stefanelli, S.; Rassu, M.; Parolin, C.; Balzarini, J.; De Clercq, E. Cellular uptake of phosphonylmethoxyalkylpurine derivatives. Antiviral Res. 1991, 16, 115-119.
9. Naesens, L.; Balzarini, J.; De Clercq, E. Therapeutic potential of PMEA as an antiviral drug. Med. Virol. 1994, 4, 147-159.
10. a) Louie, J.; Bielawski, C.W.; Grubbs, R.H. Tandem catalysis: The sequential mediation of olefin metathesis, hydrogenation and hydrogen transfer with single-component Ru complexes. J. Am. Chem. Soc. 2001, 123, 11312-11313
11. b) Kang, J.H.; Chung, H.E.; Kim, S.Y.; Kim, Y.; Lee, J.; Lewin, N.E.; Pearce, L.V.; Blumberg, P.M.; Marquez, V.E. Conformationally constrained analogues of diacylglycerol (DAG). Effect on protein kinase C (PK-C) binding by the isosteric replacement of sn-1 and sn-2 esters in DAG-lactones. Bioorg. Med. Chem. 2003, 11, 2529-2539.
12. Kim, A.; Oh, C.H.; Hong, J.H. Synthesis and anti-HCMV activity of novel cyclopropyl phosphonic acid nucleosides. Nucleosides, Nucleotides Nucleic Acids 2006, 25, 1399-1406. (Pubitemid 44655671)
13. Hossain, N.; Rozenski, J.; De Clercq, E.; Herdewijn, P. Synthesis and antiviral activity of acyclic analogues of 1,5-anhydrohexitol nucleosides using Mitsunobu reaction. Tetrahedron 1996, 52, 13655-13670.
14. El-Subbagh, H.I., Racha, S., Abushanab, E., Panzica, R.P. Synthesis of phosphonate isosteres of 2-deoxy-1,2-seco-nucleosides. J. Org. Chem. 1996, 61, 890-894.
15. Ṕerigaud, C.; Gosselin, G.; Lefebvre, I.; Girardet, J.L.; Benzaria, S.; Barber, I.; Imbach, J.L. Rational design for cytosolic delivery of nucleoside monophosphates: "SATE" and "DTE" as enzyme-labile transfer phosphate protecting groups. Bioorg. Med. Chem. Lett. 1993, 3, 2521-2526.
16. Lian, L.J.; Yoo, J.C.; Hong, J.H. Short synthesis and antiviral activity of acyclic phosphonic acid nucleoside analogues. Nucleosides Nucleotides Nucleic Acids 2009, 28, 150-164.