Synthesis of acyclic thieno[3,2-d]pyrimidine nucleosides and azido derivatives as potential anti-hiv agents.

Nucleosides and Nucleotides

Volumn 13, Issue 4, 1994, Pages 883-889

  Laduree, C Fossey ^a  

^a CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 (BENZYLOXYMETHYL)THIENO[3,2 D]PYRIMIDINE 2,4 DIONE; 1 [(2 AZIDO 1 (HYDROXYMETHYL)ETHOXYMETHYL]THIENO[3,2 D]PYRIMIDNE 2,4 DIONE; 1 [(2 AZIDOETHOXY)METHYL]THIENO[3,2 D]PYRIMIDINE 2,4 DIONE; 1 [(2 HYDROXY 1 (HYDROXYMETHYL)ETHOXYMETHYL]THIENO[3,2 D]PYRIMIDINE 2,4 DIONE; 1 [(2 HYDROXYETHOXY)METHYL]THIENO[3,2 D]PYRIMIDINE 2,4 DIONE; 1 BENZYLOXYMETHYL 5 ETHYL 6 PHENYLTHIOURACIL; 3 (BENZYLOXYMETHYL)THIENO[3,2 D]PYRIMIDINE 2,4 DIONE; ACICLOVIR; ANTIVIRUS AGENT; AZIDE; GANCICLOVIR; PYRIMIDINE NUCLEOSIDE DERIVATIVE; THIOURACIL DERIVATIVE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CYTOPATHOGENIC EFFECT; DRUG SCREENING; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; VIRUS INHIBITION;

EID: 0028331955     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257779408011862     Document Type: Article

References (17)

1. G.B. ELION, P.A. FURMAN, J.A. FYFE, P. DE MIRANDA, L. BEAUCHAMP and J.H. SCHAEFFER, Proc. Natl. Acad. Sci. USA 1977,74, 5716.
2. a) K.K. OGILVIE, U.O. CHERIYAN, B.K. RADATUS, K.O. SMITH, K.S. GALLOWAY and W.L. KENNELL, Can. J. Chem. 1982, 60, 3005.
3. b) A.K. FIELD, M.E. DAVIE, C. DEWITT, H.C. PERRY, R. LIOU, J.I. GERMERSHAUSEN, J.D. KARKAS, W.T. ASHTON, D.B.R. JOHNSON and R.C. TOLMAN, Proc. Natl. Acad. Sci. USA 1983, 80, 4139. c) J.C. MARTIN, C.A. DVORAK, D.F. SMEE, T.R. MATHEWS and J.P.H. VERHEYDEN, J. Med. Chem. 1983, 26, 759.
4. a) T. MIYASAKA, H. TANAKA, M. BABA, H. HAYAKAWA, R.T. WALKER, J. BALZARINI, E. DE CLERCQ, J. Med. Chem. 1989, 32, 2507. b) M. BABA, H. TANAKA, E. DE CLERQ, R. PAUWELS, J. BALZARINI, D. SCHOLS, H. NAKASHIMA, C.F. PERNO, R.T. WALKER, T. MIYASAKA, Biochem. Biophys. Res. Comm. 1989, 165, 1375. c) M. BABA, E. DE CLERCQ, H. TANAKA, M. UBASAWA, K. SEKIYA, I. NITTA, K. UMEZU, H. NAKASHIMA, S. MORI, S. SHIGETA, R.T. WALKER, T. MIYASAKA, Proc. Natl. Acad. USA 1991 88, 2356.
5. a) H. TANAKA, M. BABA, H. HAYAKAWA, T. SAKAMAKI, T. MIYASAKA, M. UBASAWA, H. TAKASHIMA, K. SEKIYA, I. NITTA, S.SHIGETA, R. T WALKER, J.BALZARINI, E. DE CLERCQ, J. Med. Chem. 1991, 34, 349. b) H. TANAKA, M. BABA, M. UBASAWA, H. TAKASHIMA, K. SEKIYA, I. NITTA, S. SHIGETA, R.T. WALKER, E. DE CLERCQ, T. MIYASAKA,J. Med. Chem. 1991, 34, 1394.
6. H. MITSUYA, K.J. WEINHOLD, P.A. FURMAN, M.H. ST. CLAIR, S.N. LEHRMAN, R.C. GALLO, D. BOLOGNESI, D.W. BARRY and S. BRODER,Proc. Natl. Acad. Sci. USA 1985, 82, 7096.
7. a) P. SCHEINER, A. GEER, A-M. BUCKNOR, J.L. IMBACH and R.F. SCHINAZI,J. Med. Chem. 1989, 32,73. b) K.H. LEE, Y.L. CHEN, B.R. HUANG and C.C. TSENG,Nucleosides & Nucleotides 1991,10, 1407. c) M.C. TRINH, J.C. FLORENT, D.S. GRIERSON and C. MONNERET, Tetrahedron Lett. 1991,32, 1447.
8. a) MURUTA and K. ACHIWA, Chem. Pharm. Bull. 1990, 38, 836. b) R.T. WALKER and A. KUMAR, Tetrahedron 1990, 46, 3101.
9. Brevet n°43021 M. 01 AOUT 1966 (Republique FRANCAISE), Societe K. THOMAE G.m.b.H.
10. T.B. JOHNSON and G.E.HILBERT, Science 1929, 69, 579;J. Amer. Chem. Soc. 1930,52, 2001.
11. a) U. NIEDBALLA and H. VORBRUGGEN, Angew. Chem. Internat. Ed. 1970,9., 461. b) U. NIEDBALLA and H. VORBRtJGGEN, J. Org. Chem. 1976, 41, 2084. c) H. VORBRUGGEN, K. KROLDCIEWIEZ, B. BENNUA and G. HOFLE, “Synthesis, structure, and chemistry of transfer ribonucleic acids and their components”, Polish Academy of Sciences Ed., Poznan 1976,428. d) U. NIEDBALLA and H. VORBRUGGEN,J. Org. Chem. 1974, 32, 3654.
12. A. ROSOWSKY, S.H. KIM, M. WICK,J. Med. Chem. 1981,24, 1177.
13. L. BEAUCHAMP, B. L. SERLING, J. E. KELSEY, K. K. BIRON, P. COLLINS, J. SELWAY, J. C. LIN, H. J. SCHAEFFER, J.Med.Chem. 1988,31, 144.
14. a) M. SANO, Chem. Pharm. Bull. Japan 1962,10, 320. b) J. J. FOX and D. SHUGAR, Biochim. and Biophys. Acta 1952,2, 369. c) D. SHUGAR and J. J. FOX, Biochim. and Biophys. Acta 1952,2, 199.
15. I. YAMAMOTO, M. SEKINE and T. HATA,J. C. S. Perkin trans 1 1980,306.
16. E. PRETSCH, T. CLERC, J. SEIBL and W. SIMON “Tables of Spectral Data for structure Determination of Organic Compounds” 2nd Edition Springer -Verlag 1989.
17. T. MOSMANN,J. Immunol. Methods 1983, 65, 55.