Synthesis of N9- and N7-[2-hydroxy-3- (phosphonomethoxy)-propyl] derivatives of N6-substituted adenines, 2,6-diaminopurines and related compounds

Collection of Czechoslovak Chemical Communications

Volumn 69, Issue 10, 2004, Pages 1889-1913

  Krečmerová, Marcela ^a   Masojídková, Milena ^a   Holý, Antonín ^a  

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

Author keywords

Acyclic nucleotide analogues; Antivirals; Epoxides; HPMPA; Nucleosides; Nucleotides; Oxirane ring opening; Phosphonates; Purines

Indexed keywords

9 [(2 ETHOXY 2 OXO 2 LAMBDA 5 1,4,2 DIOXAPHOSPHINAN 6 YL)METHYL] 9H PURIN 6 AMINE; 9 [(2 ETHOXY 2 OXO 2 LAMBDA 5 1,4,2 DIOXAPHOSPHINAN 6 YL)METHYL] 9H PURINE 2,6 DIAMINE; [[2 HYDROXY 3 (6 PIPERIDINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL] PHOSPHONIC ACID; [[2 HYDROXY 3 [6 [(2 HYDROXYETHYL)AMINO] 9H PURIN 9 YL]PROPOXY]METHYL] PHOSPHONIC ACID; [[2 HYDROXY 3 [6 [(2 METHOXYETHYL)AMINO] 9H PURIN 9 YL]PROPOXY]METHYL] PHOSPHONIC ACID; [[3 (2 AMINO 6 CYCLOPROPYLAMINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL] PHOSPHONIC ACID; [[3 (2 AMINO 6 DIMETHYLAMINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL] PHOSPHONIC ACID; [[3 (6 ALLYLAMINO 9H PURIN 9 YL)PROPOXY]METHYL]PHOSPHONIC ACID; [[3 (6 CYCLOPROPYLAMINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL]PHOSPHONIC ACID; [[3 (6 DIMETHYLAMINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL]PHOSPHONIC ACID; [[3 [6 [(2 DIMETHYLAMINOETHYL)AMINO] 9H PURIN 9 YL] 2 HYDROXYPROPOXY] METHYL]PHOSPHONIC ACID; DIETHYL [[2 HYDROXY 3 (6 PIPERIDINO 9H PURIN 9 YL)PROPOXY]METHYL] PHOSPHONATE; DIETHYL [[2 HYDROXY 3 [6 [(2 HYDROXYETHYL)AMINO] 9H PURIN 9 YL]PROPOXY]METHYL]PHOSPHONATE; DIETHYL [[2 HYDROXY 3 [6 [(2 METHOXYETHYL)AMINO] 9H PURIN 9 YL]PROPOXY]METHYL]PHOSPHONATE; DIETHYL [[2 HYDROXY 3 [6 [[(2,2,2 TRIFLUOROETHYLAMINO)ETHYL]AMINO] 9H PURIN 9 YL] 2 HYDROXYPROPOXY]METHYL]PHOSPHONATE; DIETHYL [[3 (2 AMINO 6 CHLORO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL] PHOSPHONATE; DIETHYL [[3 (2 AMINO 6 CYCLOPROPYLAMINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL]PHOSPHONATE; DIETHYL [[3 (2 AMINO 6 DIMETHYLAMINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY] METHYL]PHOSPHONATE; DIETHYL [[3 (6 ALLYLAMINO 2 AMINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL] PHOSPHONATE; DIETHYL [[3 (6 ALLYLAMINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL] PHOSPHONATE; DIETHYL [[3 (6 CHLORO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL]PHOSPHONATE; DIETHYL [[3 (6 CYCLOPROPYLAMINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL] PHOSPHONATE; DIETHYL [[3 (6 DIMETHYLAMINO 7H PURIN 7 YL) 2 HYDROXYPROPOXY]METHYL] PHOSPHONATE; DIETHYL [[3 (6 DIMETHYLAMINO 9H PURIN 9 YL) 2 HYDROXYPROPOXY]METHYL] PHOSPHONATE; DIETHYL [[3 [2 AMINO 6 [(2 DIMETHYLAMINOETHYL)AMINO] 9H PURIN 9 YL] 2 HYDROXYPROPOXY]METHYL]PHOSPHONATE; DIETHYL [[3 [2 AMINO 6 [(2,2,2 TRIFLUOROETHYL)AMINO] 9H PURIN 9 YL] 2 HYDROXYPROPOXY]METHYL]PHOSPHONATE; DIETHYL [[3 [6 [(2 DIMETHYLAMINOETHYL)AMINO] 9H PURIN 9 YL] 2 HYDROXYPROPOXY]METHYL]PHOSPHONATE; DIETHYL[(OXIRANYLMETHOXY)METHYL]PHOSPHONATE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; HYDROLYSIS; SUBSTITUTION REACTION;

EID: 10344231448     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20041889     Document Type: Article

References (21)

1. a) De Clercq E., Holý A., Rosenberg I., Sakuma T., Balzarini J., Maudgal P. C.: Nature 1986, 323, 464;
2. b) De Clercq E., Sakuma T., Baba M., Pauwels R., Balzarini J., Rosenberg I., Holý A.: Antiviral Res. 1987, 8, 261;
3. Holý A., Votruba I., Merta A., Černý J., Veselý J., Vlach J., Šedivá K., Rosenberg I., Otmar M., Hřebabecký H., Trávníček M., Vonka V., Snoeck R., De Clercq E.: Antiviral Res. 1990, 13, 295;
4. Holý A., Dvořáková H., Jindřich J. in: Antibiotics and Antiviral Compounds (K. Krohn, H. A. Kirst and H. Maag, Eds), p. 455. Verlag Chemie, Weinheim-New York 1993;
5. e) Holý A. in: Advances in Antiviral Drug Design (De Clercq E., Ed.), p. 179. JAI Press, Inc., Greenwich (CT) 1994;
6. f) Holý A. in: Recent Advances in Nucleosides: Chemistry and Chemotherapy (C. K. Chu, Ed.), p. 167. Elsevier, Amsterdam 2002;
7. g) Holý A.: Curr. Pharm. Des. 2003, 9, 2567.
8. Baba M., Konno K., Shigeta S., De Clercq E.: Eur. J. Clin. Microbiol. Infect. Dis. 1987, 6, 158.
9. Terry B. J., Mazina K. E., Tuomari A. V., Haffey M. L., Hagen M., Feldman A., Slusarchyk W. A., Young M. G., Zahler R., Field A. K.: Antiviral Res. 1988, 10, 235.
10. Holý A.: Collect. Czech. Chem. Commun. 1993, 58, 649.
11. a) Naesens L., De Clercq E.: Nucleosides Nucleotides 1997, 16, 983;
12. b) Rahhal F. M., Arevalo J. F., Munguia D., Taskintuna I., Delapaz E. C., Azen S. P., Freeman W. R.: Ophthalmology 1996, 103, 1078;
13. De Clercq E.: Collect. Czech. Chem. Commun. 1998, 63, 480.
14. Rosenberg I., Holý A.: Collect. Czech. Chem. Commun. 1982, 47, 3447.
15. Webb R. R., Martin J. C.: Tetrahedron Lett. 1987, 28, 4963.
16. Holý A., Rosenberg I.: Collect. Czech. Chem. Commun. 1987, 52, 2775.
17. Holý A., Rosenberg I., Dvořáková H.: Collect. Czech. Chem. Commun. 1989, 54, 2470.
18. Rosenberg I., Holý A.: Collect. Czech. Chem. Commun. 1987, 52, 2792.
19. Holý A., Votruba I., Tloušt'ová E., Masojídková M.: Collect. Czech. Chem. Commun. 2001, 66, 1545.
20. Orlov N. F., Viktorov O. F., Elkina N. S.: Dokl. Akad. Nauk SSSR 1966, 166, 378.
21. Arbuzov B. A., Bogonostseva N. P.: Zh. Obshch. Khim. 1959, 29, 2617.