Synthesis of ester prodrugs of 9-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl] -2,6-diaminopurine (HPMPDAP) as anti-poxvirus agents

Journal of Medicinal Chemistry

Volumn 53, Issue 19, 2010, Pages 6825-6837

  Krečmerová, Marcela ^a   Holý, Antonín ^a   Andrei, Graciela ^b   Pomeisl, Karel ^a   Tichý, Tomáš ^a   Břehová, Petra ^a   Masojídková, Milena ^a   Dračínský, Martin ^a   Pohl, Radek ^a   Laflamme, Genevieve ^c   Naesens, Lieve ^b   Hui, Hon ^c   Cihlar, Tomas ^c   Neyts, Johan ^b   De Clercq, Erik ^b   Balzarini, Jan ^b   Snoeck, Robert ^b  

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

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^c GILEAD SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (2 BROMOVINYL) 2' DEOXYURIDINE; 9 [(2 HYDROXY 2 OXIDO 1,4,2 DIOXAPHOSPHINAN 5 YL)METHYL] 2,6 DIAMINOPURINE; 9 [3 HYDROXY 2 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; ACICLOVIR; ANTIVIRUS AGENT; BIS(2,2,2 TRIFLUOROETHYL)TOSYLOXYMETHYLPHOSPHONATE; ISOPROPYL TERT BUTYLOXYCARBONYL L VALYL L SERINATE; L SERINE ISOPROPYL ESTER HYDROCHLORIDE; PRODRUG; UNCLASSIFIED DRUG; 9-(3-HYDROXY-2-PHOSPHONOMETHOXYPROPYL)-2,6-DIAMINOPURINE; ADENINE; ESTER; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CELL GROWTH; CELL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; EVALUATION; HERPES VIRUS; HUMAN; HUMAN CELL; POXVIRUS INFECTION; VACCINIA VIRUS; VIRUS INHIBITION; VIRUS REPLICATION; ANALOGS AND DERIVATIVES; CELL CULTURE; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; HERPESVIRIDAE; POXVIRIDAE; PROCEDURES; RNA VIRUS; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; VIROLOGY;

ADENINE; ANTIVIRAL AGENTS; CELL PROLIFERATION; CELLS, CULTURED; ESTERS; HERPESVIRIDAE; HUMANS; ORGANOPHOSPHORUS COMPOUNDS; POXVIRIDAE; PRODRUGS; RNA VIRUSES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; VIROLOGY;

EID: 77957900154     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901828c     Document Type: Article

References (47)

1. Hruby, D. E.; Guarino, L. A.; Kates, J. R. Vaccinia virus replication. I. Requirement for the host-cell nucleus J. Virol. 1979, 29, 705-715
2. Sliva, K.; Schnierle, B. From actually toxic to highly specific - novel drugs against poxviruses Virol. J. 2007, 4, 8
3. Harrison, S. C.; Alberts, B.; Ehrenfeld, E.; Enquist, L.; Fineberg, H.; McKnight, S. L.; Moss, B.; O'Donnell, M.; Ploegh, H.; Schmid, S. L.; Walter, K. P.; Theriot, J. Discovery of antivirals against smallpox Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11178-11192
4. Vora, S.; Damon, I.; Fulginiti, V.; Weber, S. G.; Kahana, M.; Stein, S. L.; Gerber, S. I.; Garcia-Houchins, S.; Lederman, E.; Hruby, D.; Collins, L.; Scott, D.; Thompson, K.; Barson, J. V.; Regnery, R.; Hughes, C.; Daum, R. S.; Li, Y.; Zhao, H.; Smith, S.; Braden, Z.; Karem, K.; Olson, V.; Davidson, W.; Trindade, G.; Bolken, T.; Jordan, R.; Tien, D.; Marcinak, J. Severe eczema vaccinatum in a household contact of a smallpox vaccinee Clin. Infect. Dis. 2008, 46, 1555-1561
5. CDC. Progressive vaccinia in a military smallpox vaccinee. Unites States, 2009 MMWR 2009, 58, 1-4
6. Field, H. J.; De Clercq, E. Antiviral chemistry and chemotherapy's current antiviral agents FactFile (2nd ed.): DNA viruses Antiviral Chem. Chemother. 2008, 19, 51-62
7. Tse-Dinh, Y. C. An update on the development of drugs against smallpox Curr. Opin. Investig. Drugs 2008, 9, 865-870
8. De Clercq, E. Antiviral activity spectrum and target of action of different classes of nucleoside analogs Nucleosides, Nucleotides Nucleic Acids 1994, 13, 1271-1295
9. Borchardt, R. T. S-Adenosyl- l -methionine-dependent macromolecule methyltransferases: potential tergets for the design of chemotherapeutic agents J. Med. Chem. 1980, 23, 347-357
10. De Clercq, E. Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections Clin. Microbiol. Rev. 2001, 14, 382-397
11. Snoeck, R.; Holý, A; Dewolf-Peeters, C.; Van Den Oord, J.; De Clercq, E.; Andrei, G. Antivaccinia activities of acyclic nucleoside phosphonate derivatives in epithelial cells and organotypic cultures Antimicrob. Agents Chemother. 2002, 46, 3356-3361
12. Krečmerová, M.; Holý, A.; Pískala, A.; Masojídková, M.; Balzarini, J.; Andrei, G.; Snoeck, R.; Naesens, L.; Neyts, J.; De Clercq, E. Triazine analogs of 1-(S)- [3-hydroxy-2- (phosphonomethoxy)propyl]cytosine (cidofovir) and related compounds J. Med. Chem. 2007, 50, 1069-1077
13. Holý, A. Syntheses of enantiomeric N-(3-hydroxy-2- phosphonomethoxypropyl) derivatives of purine and pyrimidine bases Collect. Czech. Chem. Commun. 1993, 58, 649-674
14. Holý, A.; Dvoraková, H.; Jindrich, J.; Masojí dková, M.; Budesinský, M.; Balzarini, J.; Andrei, G.; De Clercq, E. Acyclic nucleotide analogs derived from 8-azapurines: synthesis and antiviral activity J. Med. Chem. 1996, 39, 4073-4088
15. De Clercq, E.; Andrei, G.; Balzarini, J.; Leyssen, P.; Naesens, L.; Neyts, J.; Pannecouque, C.; Snoeck, R.; Ying, C.; Hocková, D.; Holý, A. Antiviral potential of a new generation of acyclic nucleoside phosphonates, the 6-[2-(phosphonomethoxy)alkoxy]-2,4-diaminopyrimidines Nucleosides, Nucleotides Nucleic Acids 2005, 24, 331-341
16. Duraffour, S.; Snoeck, R.; Krečmerová, M.; van Den Oord, J.; De Vos, R.; Holý, A.; Crance, J.-M.; Garin, D.; De Clercq, E.; Andrei, G. Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models Antimicrob. Agents Chemother. 2007, 51, 4410-4419
17. Centers for Disease Control and Prevention Smallpox vaccine adverse events monitoring and response system for the first stage of the smallpox vaccination program Morb. Mortal. Wkly. Rep. 2003, 52, 88-89
18. De Clercq, E. Clinical potential of the acyclic nucleoside phosphonates cidofovir, adefovir and tenofovir in treatment of DNA virus and retrovirus infections Clin. Microbiol. Rev. 2003, 16, 569-596 (Pubitemid 37296550)
19. Buller, R. M.; Owens, G.; Schriever, J.; Melman, L.; Beadle, J. R.; Hostetler, K. Y. Efficacy of oral active ether lipid analogs of cidofovir in a lethal mousepox model Virology 2004, 318, 474-481
20. Kern, E. R.; Hartline, C.; Harden, E.; Keith, K.; Rodriguez, N.; Beadle, J. R.; Hostetler, K. Y. Enhanced inhibition of orthopoxvirus replication in vitro by alkoxyalkyl esters of cidofovir and cyclic cidofovir Antimicrob. Agents Chemother. 2002, 46, 991-995
21. Keith, K. A.; Wan, W. B.; Ciesla, S. L.; Beadle, J. R.; Hostetler, K. Y.; Kern, E. R. Inhibitory activity of alkoxyalkyl and alkyl esters of cidofovir and cyclic cidofovir against orthopoxvirus replication in vitro Antimicrob. Agents Chemother. 2004, 48, 1869-1871
22. Morris, K. Oral drug and old vaccine renew smallpox bioterror debate Lancet Infect. Dis. 2002, 2, 262-262
23. Bradbury, J. Orally available cidofovir derivative active against smallpox Lancet 2002, 359, 1041-1041
24. Valiaeva, N.; Prichard, M. N.; Buller, R. M.; Beadle, J. R.; Hartline, C. B.; Keith, K. A.; Schriewer, J.; Trahan, J.; Hostetler, K. Y. Antiviral evaluation of octadecyloxyethyl esters of (S)-3-hydroxy-2-(phosphonomethoxy) propyl nucleosides against herpesviruses and orthopoxviruses Antiviral Res. 2009, 84, 254-259
25. Andrei, G.; Gammon, D. B.; Fiten, P.; Krečmerová, M.; Holý, A.; De Clercq, E.; Opdenakker, G.; Snoeck, R.; Evans, D. H. On the mechanism of antiviral drug resistance of vaccinia virus: identification of residues in the viral DNA polymerase conferring differential resistance to anti-poxvirus drugs J. Virol. 2008, 82, 12520-12534
26. Naesens, L.; Neyts, J.; Balzarini, J.; Bischofberger, N.; De Clercq, E. In vivo antiretroviral efficacy of oral bis(POM)-PMEA, the bis(pivaloyloxymethyl) prodrug of 9-(2-phosphonylmethoxyethyl)adenine (PMEA) Nucleosides Nucleotides 1995, 14, 767-770
27. Noble, S.; Goa, K. L. Adefovir dipivoxil Drugs 1999, 58, 479-487
28. Naesens, L.; Bischofberger, N.; Augustijns, P.; Annaert, P.; Vandenmooter, G.; Arimilli, M. N.; Kim, C. U.; De Clercq, E. Antiretroviral efficacy and pharmacokinetics of oral bis(isopropyloxy) 9-(2- phosphonylmethoxypropyl)adenine in mice Antimicrob. Agents Chemother. 1998, 42, 1568-1573
29. Schooley, R.T.; Ruane, P.; Myers, R. A.; Beall, G.; Lampiris, H.; Berger, D.; Chen, S. S.; Miller, M. D.; Isaacson, E.; Cheng, A. K. Tenofovir DF in antiretroviral-experienced patients: results from a 48-week, randomized, double-blind study AIDS 2002, 16, 1257-1263
30. Krečmerová, M.; Holý, A.; Pohl, R.; Masojidková, M.; Andrei, G.; Naesens, L.; Neyts, J.; Balzarini, J.; De Clercq, E.; Snoeck, R. Ester prodrugs of cyclic 1-(S)-[3-hydroxy-2- (phosphonomethoxy)propyl]-5-azacytosine: synthesis and antiviral activity J. Med. Chem. 2007, 50, 5765-5772
31. Sekiya, K.; Takashima, H.; Ueda, N.; Kamiya, N.; Yuassa, S.; Fujimura, Y.; Ubasawa, M. 2-Amino-6-arylthio-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) esters as novel HBV-specefic antiviral reagents J. Med. Chem. 2002, 45, 3138-3142
32. Kamiya, N.; Kubota, A.; Iwase, Y.; Sekiya, K.; Ubasawa, M.; Yuasa, S. Antiviral activities of MCC-478, a novel and specific inhibitor of hepatitis B virus Antimicrob. Agents Chemother. 2002, 46, 2872-2877
33. Han, S.-Y.; Kim, Y.-A. Recent development of peptide coupling reagents in organic synthesis Tetrahedron 2004, 60, 2447-2467
34. Serafinowska, H. T.; Ashton, R. J.; Bailey, S.; Harnden, M. R.; Jackson, S. M.; Sutton, D. Synthesis and in vivo evaluation of prodrugs of 9-[2-(phosphonomethoxy)ethoxyadenine J. Med.Chem. 1995, 38, 1372-1379
35. Shaw, J. P.; Louie, M. S.; Krishnamurthy, V. V.; Arimilli, M. N.; Jones, R. J.; Bidgood, A. M.; Lee, W. A.; Cundy, K. C. Pharmacokinetics and metabolism of selected prodrugs of PMEA in rats Drug Metab. Dispos. 1997, 25, 362-366
36. Oliyai, R.; Shaw, J.-P.; Sueoka-Lennen, C. M.; Cundy, K. C.; Arimilli, M. N.; Jones, R. J.; Lee, W. A. Aryl ester prodrugs of cyclic HPMPC. I. Physicochemical characterization and in vitro biological stability Pharm. Res. 1999, 16, 1687-1693
37. Oliyai, R.; Arimilli, M. N.; Jones, R. J.; Lee, W. A. Parmacokinetics of salicylate ester prodrugs of cyclic HPMPC in dogs Nucleosides, Nucleotides Nucleic Acids 2001, 20, 1411-1414
38. Beauchamp, L. M.; Orr, G. F.; De Miranda, P.; Burnette, T.; Krenitsky, T. A. Amino-acid ester prodrugs of acyclovir Antiviral Chem. Chemother. 1992, 3, 157-164
39. Colla, L.; De Clercq, E.; Busson, R.; Vanderhaeghe, H. Synthesis and antiviral activity of water-soluble esters of acyclovir [9-([(2-hydroxyethoxy) methyl]guanine] J. Med. Chem. 1983, 26, 602-604
40. Pauletti, G. M.; Gangwar, S.; Siahaan, T. J.; Aube, J.; Borchardt, R. T. Improvement of oral peptide bioavailability: Peptidomimetics and prodrug strategies Adv. Drug Deliv. Rev. 1997, 27, 235-256
41. Peterson, L. W.; Kashemirov, B. A.; Blazewska, K. M.; Breitenback, J.; Borysko, K.; Drach, J. C.; Kim, J. S.; Kijek, P.; Hilfinger, J. M.; McKenna, C. E. Synthesis and structure-activity aspects of some cyclic cidofovir peptidomimetic prodrugs Antiviral Res. 2007, 74, A33
42. Peterson, L. W.; Kashemirov, B. A.; Eriksson, U.; Kim, J.-S.; Mitchell, S.; Kijek, P.; Lee, K.-D.; Hilfinger, J. M.; McKenna, C. E. Serine-side chain-linked peptidomimetic prodrugs of cidofovir and cyclic cidofovir: C-ester effects on transport and activation Antiviral Res. 2008, 78, A46
43. Valiaeva, N; Prichard, M. N.; Buller, R; Beadle, J. R.; Hartline, C. B.; Keith, K. A.; Schriever, J.; Trahan, J.; Hostetler, K. Y. Antiviral evaluation of octadecyloxyethyl esters of (S)-3-hydroxy-2-(phosphonomethoxy)propyl nucleosides against herpesviruses and orthopoxviruses Antiviral Res. 2009, 84, 254-259
44. Valiaeva, N; Beadle, J. R.; Aldern, K. A.; Trahan, J.; Hostetler, K. Y. Synthesis and antiviral evaluation of alkoxyalkyl esters of acyclic purine and pyrimidine nucleoside phosphonates against HIV-1 in vitro Antiviral Res. 2006, 72, 10-19
45. Valiaeva, N; Aldern, K. A.; Trahan, J.; Beadle, J. R.; Hostetler, K. Y. Synthesis and evaluation of five esters of 3-hydroxy-2-(phosphonomethoxy)propyl nucleoside phosphonates in HIV-1 infected cells Antiviral Res. 2008, 78, A49
46. Painter, R. G.; Almond, M. R.; Trost, L. C.; Lampert, B. M.; Neyts, J.; De Clercq, E.; Korba, B. E.; ALdern, K.; Beadle, J. R.; Hostetler, K. Y. Evaluation of hexadecyloxypropyl-9-R-[2-(phosphonomethoxy)propyl]-adenine, CMX157, as a potential treatment for human immunodeficiency virus type 1 and hepatitis B virus infections Antimicrob. Agents Chemother. 2007, 51, 3505-3509
47. Singh, R. S.; Mukherjee, K.; Banerjee, R.; Chaudhuri, A.; Hait, S. K.; Moulik, S. P.; Ramadas, Y.; Vijayalakshmi, A.; Rao, N. M. Anchor dependency for non-glycerol based cationic lipofectins: mixed bag of regular and anomalous transfection profiles Chem. - Eur. J. 2002, 8, 900-909