Synthesis and antiviral evaluation of novel 5′-norcarboacyclic phosphonic acid nucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 25, Issue 8, 2006, Pages 941-950

  Kim, Aihong ^a   Hong, Joon ^a  

^a Chosun University   (South Korea)

Author keywords

5 Noraristeromycin; Antiviral agent; Carboacyclic nucleoside; Nucleotide

Indexed keywords

1 [1 (HYDROXYMETHYL)CYCLOBUTYLMETHYLPHOSPHONIC ACID]ADENINE; 1 [1 (HYDROXYMETHYL)CYCLOBUTYLMETHYLPHOSPHONIC ACID]CYTOSINE; 1 [1 (HYDROXYMETHYL)CYCLOBUTYLMETHYLPHOSPHONIC ACID]THYMINE; 1 [1 (HYDROXYMETHYL)CYCLOBUTYLMETHYLPHOSPHONIC ACID]URACIL; 1 [1 (HYDROXYMETHYL)CYCLOPENT 3 ENYLMETHYLPHOSPHONIC ACID]CYTOSINE; 1 [1 (HYDROXYMETHYL)CYCLOPENT 3 ENYLMETHYLPHOSPHONIC ACID]THYMINE; 1 [1 (HYDROXYMETHYL)CYCLOPENT 3 ENYLMETHYLPHOSPHONIC ACID]URACIL; 9 [1 (HYDROXYMETHYL)CYCLOPENT 3 ENYLMETHYLPHOSPHONIC ACID]ADENINE; ACICLOVIR; ANTIVIRUS AGENT; GANCICLOVIR; NUCLEOSIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DEPROTECTION REACTION; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; POLYMERIZATION;

ANTIVIRAL AGENTS; PHOSPHONIC ACIDS; PYRIMIDINE NUCLEOSIDES;

EID: 33746809459     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770600793927     Document Type: Article

References (14)

1. El Ashry, E.S.H.; El Kilany, Y. Acyclonucleosides: Part 3. Advances in Heterocyclic Chemistry, 1997, 69, 135-153.
2. Agrofoglio, L.A.; Challand, S.R. Acyclic, Carbocyclic and l-Nucleosides. Kluwer Academic Publishers, Philadelphia, 1998, 136-137.
3. Vandendriessche, F.; Snoeck, R.; Janssen, G.; Hoogmartens, J.; Van Aerschot, A.; De Clercq, E.; Herdwijn, P. Synthesis and Antiviral Activity of Acyclic Nucleosides with a 3(S),5-Dihydroxypentyl or 4(R)-Methoxy-3(S),5- Dihydroxypentyl Side Chain. Journal of Medicinal Chemistry 1992, 35, 1458-1465.
4. Balzarini, J.; Aquaro, S.; Perno, C.F.; Witvrouw, M.; Holy, A.; De Clercq, E. Activity of the (R)-Enantiomers of 9-(2-Phosphonylmethoxypropyl)- Adenine and 9-(2-Phosphonylmethoxy propyl)-2,6-Diaminopurine against HIV in Different Human Cell Systems. Biochemical & Biophysical Research Communications 1996, 219, 337-341.
5. 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. Antimicrobial Agents in Chemotherapy 1988, 32, 1025-1030.
6. De Clercq, E. Potential of Acyclic Nucleoside Phosphonates in the Treatment of DNA Virus and Retrovirus Infections. Expert Review of Anti-infective Therapy 2003, 1, 21-43.
7. Robbins, B.L.; Srinivas, R.V.; Bischofberger, N.; Fridland, A. Anti-Human Immunodeficiency Virus Activity and Cellular Metabolism of a Potential Prodrug of the Acyclic Nucleoside Phosphonate 9-R-(2-Phosphonomethoxypropyl)Adenine (PMPA), bis(Isopropyloxymethylcarbonyl) PMPA. Antimicrobial Agents in Chemotherapy 1998, 42, 612-617.
8. Siddiqi, S.M.; Chen, X.; Schneller, S.W.; Ikeda, S.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. An Epimer of 5′-Noraristeromycin and Its Antiviral Properties. Journal of Medicinal Chemistry 1994, 37, 1382-1384.
9. Hamzeh, F.M.; Lietman, P.S. Intranuclear Accumulation of Subgenomic Noninfectious Human Cytomegalovirus DNA in Infected Cells in the Presence of Ganciclovir. Antimicrobial Agents in Chemotherapy 1991, 35, 1818-1823.
10. Chatis, P.A.; Crumpacker, C.S. Resistance of Herpesviruses to Antiviral Drugs. Antimicrobial Agents in Chemotherapy 1992, 36, 1589-1595.
11. Zelinskii, N.D.; Uyedinov, M.N. 1,1-Dimethy Cyclobutane. Ber. 1913, 46, 1093-1094.
12. Hong, J.H.; Ko, O.H. Synthesis and Antiviral Evaluation of Novel Acyclic Nucleosides. Bulletin of the Korean Chemical Society 2003, 24, 1284-1288.
13. El Subbagh, H.I.; Racha, S.; Abushanab, E.; Panzica, R.P. Synthesis of Phosphonate Isosteres of 2′-Deoxy-1′,2′-seco-Nucleosides. Journal of Organic Chemistry 1996, 61, 890-894.
14. Kim, H.S.; Jacobson, K.A. Synthesis of a Novel Conformationally Locked Carbocyclic Nucleoside Ring System. Organic Letters 2003, 5, 1665-1668.