Antiviral acyclic nucleoside phosphonates structure activity studies

Antiviral Research

Volumn 71, Issue 2-3 SPEC. ISS., 2006, Pages 248-253

  Holý, Antonín ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Acyclic nucleotide analogues; Adefovir; Cidofovir; Open ring ANP analogues; Tenofovir

Indexed keywords

1,2,4 TRIAZINE DERIVATIVE; 2,4 DIAMINOPYRIMIDINE DERIVATIVE; 2,6 DIAMINOPURINE DERIVATIVE; 9 (2,3 DIHYDROXYPROPYL)ADENINE; 9 (3 HYDROXY 2 PHOSPHONOMETHOXYPROPYL)ADENINE; 9 [2 AMINO 6 (4 METHOXYPHENYLSULFANYL)]PURINE; ACYCLIC NUCLEOSIDE; ADEFOVIR; ADEFOVIR DIPIVOXIL; ANTIRETROVIRUS AGENT; ANTIVIRUS AGENT; AZAURIDINE; BROXURIDINE; CIDOFOVIR; CYTARABINE; CYTOKINE; CYTOSTATIC AGENT; EMTRICITABINE PLUS TENOFOVIR DISOPROXIL; ESTER DERIVATIVE; NUCLEOTIDE; NUCLEOTIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORIC ACID; PRODRUG; PYRIMIDINE DERIVATIVE; TENOFOVIR; TENOFOVIR DISOPROXIL; TRIAZINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIDARABINE;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ACUTE TOXICITY; AIDS PATIENT; ANTIINFLAMMATORY ACTIVITY; ANTIVIRAL ACTIVITY; COMORBIDITY; CYTOMEGALOVIRUS; CYTOMEGALOVIRUS INFECTION; CYTOSTASIS; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME DEGRADATION; GENOTOXICITY; HEPATITIS B; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; IMMUNOMODULATION; IN VIVO STUDY; LIPOPHILICITY; MONKEYPOX; NEPHROTOXICITY; NONHUMAN; PAPILLOMA VIRUS; PRIORITY JOURNAL; SHORT SURVEY; SMALLPOX; STRUCTURE ACTIVITY RELATION; VIRUS INFECTION; VIRUS KERATITIS;

ANTIVIRAL AGENTS; DNA VIRUS INFECTIONS; DNA VIRUSES; HUMANS; NUCLEOSIDES; PHOSPHONIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

DNA VIRUSES; HEPATITIS B VIRUS;

EID: 33747123642     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.antiviral.2006.06.002     Document Type: Short Survey

References (19)

1. Balzarini J., Holy A., Jindrich J., Dvorakova H., Hao Z., Snoeck R., Herdewijn P., Johns D.G., and de C.E. 9-[(2RS)-3-Fluoro-2-phosphonylmethoxypropyl] derivatives of purines: a class of highly selective antiretroviral agents in vitro and in vivo. Proc. Natl. Acad. Sci. U.S.A. 88 (1991) 4961-4965
2. Balzarini J., Holy A., Jindrich J., Naesens L., Snoeck R., Schols D., and de C.E. Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)-2,6-diaminopurine. Antimicrob. Agents Chemother. 37 (1993) 332-338
3. Cesnek M., Holy A., Masojidkova M., and Zidek Z. Synthesis of 9-alkyl and 9-heteroalkyl substituted 2-amino-6-guanidinopurines and their influence on the NO-production in macrophages. Bioorg. Med. Chem. 13 (2005) 2917-2926
4. De Clercq E., and Holy A. Acyclic nucleoside phosphonates: a key class of antiviral drugs. Nat. Rev. Drug Discov. 4 (2005) 928-940
5. De Clercq E., Andrei G., Balzarini J., et al. Antiviral potential of a new generation of acyclic nucleoside phosphonates, the 6-[2-(phosphonomethoxy)alkoxy]-2,4-diaminopyrimidines. Nucleos. Nucleot. Nucl. Acids 24 (2005) 331-341
6. Dvorakova H., Masojidkova M., Holy A., Balzarini J., Andrei G., Snoeck R., and De Clercq E. Synthesis of 2′-aminomethyl derivatives of N-(2-(phosphonomethoxy)ethyl) nucleotide analogues as potential antiviral agents. J. Med. Chem. 39 (1996) 3263-3268
7. Hajek M., Matulova N., Votruba I., Holy A., and Tloust'ova E. Inhibition of human telomerase by diphosphates of acyclic nucleoside phosphonates. Biochem. Pharmacol. 70 (2005) 894-900
8. Hartmann K., Kuffer M., Balzarini J., Naesens L., Goldberg M., Erfle V., Goebel F.D., de C.E., Jindrich J., Holy A., Bischofberger N., and Kraft W. Efficacy of the acyclic nucleoside phosphonates (S)-9-(3-fluoro-2-phosphonylmethoxypropyl)adenine (FPMPA) and 9-(2-phosphonylmethoxyethyl)adenine (PMEA) against feline immunodeficiency virus. J. Acquir. Immune Defic. Syndr. Hum. Retrovirol. 17 (1998) 120-128
9. Hockova D., Holy A., and Masojidkova M. 5-Substituted-2,4-diamino-6-[2-(phosphonomethoxy)ethoxy]pyrimidines-acyclic nucleoside phosphonate analogues with antiviral activity. J. Med. Chem. 46 (2003) 5064-5073
10. Holy A., Votruba I., Masojidkova M., et al. 6-[2-(Phosphonomethoxy)alkoxy]pyrimidines with antiviral activity. J. Med. Chem. 45 (2002) 1918-1929
11. Holy A. Phosphonomethoxyalkyl analogs of nucleotides. Curr. Pharm. Des. 9 (2003) 2567-2592
12. Otova B., Holy A., Votruba I., Sladka M., Bila V., Mejsnarova B., and Leskova V. Genotoxicity of purine acyclic nucleotide analogs. Folia Biol. (Praha) 43 (1997) 225-229
13. Schinkmanova, M., Votruba, I., Holy, A., 2006. N(6)-Methyl-AMP aminohydrolase activates N(6)-substituted purine acyclic nucleoside phosphonates. Biochem. Pharmacol.
14. Stittelaar K.J., Neyts J., Naesens L., et al. Antiviral treatment is more effective than smallpox vaccination upon lethal monkeypox virus infection. Nature 439 (2006) 745-748
15. Votruba I., Pomeisl K., Tloust'ova E., Holy A., and Otova B. Inhibition of thymidine phosphorylase (PD-ECGF) from SD-lymphoma by phosphonomethoxyalkyl thymines. Biochem. Pharmacol. 69 (2005) 1517-1521
16. Ying C., Holy A., Hockova D., Havlas Z., De Clercq, and Neyts J. Novel acyclic nucleoside phosphonate analogues with potent anti-hepatitis B virus activities. Antimicrob. Agents Chemother. 49 (2005) 1177-1180
17. Zidek Z., Potmesil P., and Holy A. Cytostatic activity of antiviral acyclic nucleoside phosphonates in rodent lymphocytes. Toxicol. Appl. Pharmacol. 192 (2003) 246-253
18. Zidek Z., Potmesil P., Kmonickova E., and Holy A. Immunobiological activity of N-[2-(phosphonomethoxy)alkyl] derivatives of N6-substituted adenines, and 2,6-diaminopurines. Eur. J. Pharmacol. 475 (2003) 149-159
19. Zidek Z., Kmonickova E., and Holy A. Involvement of adenosine A1 receptors in upregulation of nitric oxide by acyclic nucleotide analogues. Eur. J. Pharmacol. 501 (2004) 79-86