Tricyclic etheno analogs of PMEG and PMEDAP: Synthesis and biological activity

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 23, 2006, Pages 8057-8065

  Hořejší, Kateřina ^a   Andrei, Graciela ^b   Clercq, Erik De ^b   Snoeck, Robert ^b   Pohl, Radek ^a   Holý, Antonín ^a  

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

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Acyclic nucleoside phosphonates; Antiviral; Chloroacetaldehyde; Purines

Indexed keywords

2 [4 (AMINO 1H IMIDAZO[2,1 B]PURIN 1 YL)ETHOXY]METHYLPHOSPHONIC ACID; 2 [4 (DIETHYLAMINO 1H IMIDAZO[2,1 B]PURIN 1 YL)ETHOXY]METHYLPHOSPHONIC ACID; 2 [4 (DIMETHYLAMINO 1H IMIDAZO[2,1 B]PURIN 1 YL)ETHOXY]METHYLPHOSPHONIC ACID; 2 [4 (PYRROLIDIN 1 YL 1H IMIDAZO[2,1 B]PURIN 1 YL)ETHOXY]METHYLPHOSPHONIC ACID; 2 [9 (AMINO 3H IMIDAZO[1,2 A]PURIN 3 YL)ETHOXY]METHYLPHOSPHONIC ACID; 2 [9 (CYCLOPROPYLIMINO 5,9 DIHYDRO 3H IMIDAZO[1,2 A]PURIN 3 YL)ETHOXY]METHYLPHOSPHONIC ACID; 2 [9 (DIMETHYLAMINO 3H IMIDAZO[1,2 A]PURIN 3 YL)ETHOXY]METHYLPHOSPHONIC ACID; 2 [9 (PYRROLIDIN 1 YL 3H IMIDAZO[1,2 A]PURIN 3 YL)ETHOXY]METHYLPHOSPHONIC ACID; ACICLOVIR; ANTIVIRUS AGENT; CIDOFOVIR; CYTOSTATIC AGENT; GANCICLOVIR; PHOSPHONIC ACID DERIVATIVE; SODIUM [2 (9 OXO 5,9 DIHYDRO 3H IMIDAZO[1,2 A]PURIN 3 YL)ETHOXY] METHYLPHOSPHONATE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CELL STRUCTURE; CONTROLLED STUDY; CYTOSTASIS; CYTOTOXICITY; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; EMBRYO; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; NONHUMAN; VARICELLA ZOSTER VIRUS; VIRUS STRAIN;

ADENINE; ANTIVIRAL AGENTS; CELL PROLIFERATION; CYTOMEGALOVIRUS; GUANINE; HERPESVIRUS 3, HUMAN; HUMANS; ORGANOPHOSPHORUS COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN HERPESVIRUS 3; HUMAN HERPESVIRUS 5;

EID: 33750035515     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.07.036     Document Type: Article

References (32)

1. Holy A. Curr. Pharm. Des. 9 (2003) 2567
2. De Clercq E., and Holy A. Nat. Rev. Drug Disc. 4 (2005) 928
3. Holy A., Gunter J., Dvorakova H., Masojidkova M., Andrei G., Snoeck R., Balzarini J., and De Clercq E. J. Med. Chem. 42 (1999) 2064
4. Holy A., Votruba I., Tloustova E., and Masojidkova M. Collect. Czech. Chem. Commun. 66 (2001) 1545
5. Merta A., Vesely J., Votruba I., Rosenberg I., and Holy A. Neoplasma 37 (1990) 111
6. Krejcova R., Horska K., Votruba I., and Holy A. Collect. Czech. Chem. Commun. 65 (2000) 1653
7. Krejcova R., Horska K., Votruba I., and Holy A. Biochem. Pharmacol. 60 (2000) 1907
8. Sediva K., Ananiev A.V., Votruba I., Holy A., and Rosenberg I. Int. J. Purine Pyrim. Res. 2 (1991) 35
9. Otova B., Zidek Z., Holy A., Votruba I., Sladka M., Marinov M., and Leskova V. In Vivo 11 (1997) 163
10. Otova B., Francova K., Franek F., Koutnik P., Votruba I., Holy A., Sladka M., and Schramlova J. Anticancer Res. 19 (1999) 3173
11. Bobkova K., Otova B., Marinov I., Mandys V., Panczak A., Votruba I., and Holy A. Anticancer Res. 20 (2000) 1041
12. Holy A., Zidek Z., and Votruba I. Collect. Czech. Chem. Commun. 61 (1996) S182
13. Hatse S., Naesens L., De Clercq E., and Balzarini J. Biochem. Pharmacol. 58 (1999) 311
14. Sattsangi P.D., Leonard N.J., and Frihart C.T. J. Org. Chem. 42 (1977) 3292
15. Kusmierek J.T., Jensen D.E., Spengler S.J., Stolarski R., and Singer B. J. Org. Chem. 52 (1987) 2374
16. Khazanchi R., Yu P.-L., and Johnson F. J. Org. Chem. 58 (1993) 2552
17. Virta P., Koch A., Roslund M.U., Mattjus P., Kleinpeter E., Kronberg L., Sjoeholm R., and Klika K.D. Org. Biomol. Chem. 3 (2005) 2924
18. Sattsangi P.D., Barrio J.R., and Leonard N.J. J. Am. Chem. Soc. 102 (1980) 770
19. Inoue Y., Kuramochi T., Sakurai M., and Tazawa I. J. Am. Chem. Soc. 102 (1980) 5574
20. Lee T. Biochemistry 16 (1977) 5403
21. Devadas B., and Leonard N.J. J. Am. Chem. Soc. 112 (1990) 3125
22. Dvorakova H., Holy A., and Masojidkova M. Collect. Czech. Chem. Commun. 53 (1988) 1779
23. Hosseini M., Blacker A.J., and Lehn J.-M. J. Am. Chem. Soc. 112 (1990) 3896
24. Kronberg L., Asplund D., Maeki J., and Sjoeholm R. Chem. Res. Toxicol. 9 (1996) 1257
25. Zhang F.-J., and Sih C.J. Bioorg. Med. Chem. Lett. 6 (1996) 2311
26. Virta P., Holmstroem T., Roslund M.U., Mattjus P., Kronberg L., and Sjoeholm R. Org. Biomol. Chem. 2 (2004) 821
27. Roslund M.U., Virta P., and Klika K.D. Org. Lett. 6 (2004) 2673
28. Boryski J., Golankiewicz B., and De Clercq E. J. Med. Chem. 31 (1988) 1351
29. Golankiewicz B., Ostrowski T., Andrei G., Snoeck R., and De Clercq E. J. Med. Chem. 37 (1994) 3187
30. Boryski J., Golankiewicz B., and De Clercq E. J. Med. Chem. 34 (1991) 2380
31. Boryski J. Nucleosides Nucleotides 9 (1990) 803 (and references cited herein)
32. Horejsi K., Pohl R., and Holy A. Collect. Czech. Chem. Commun. 71 (2006) 77