Synthesis and antiviral screening of some thieno[2,3- d]pyrimidine nucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 25, Issue 1, 2006, Pages 17-28

  Rashad, A ^a   Ali, M ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Cyclic and acyclic nucleosides; HAV; HSV 1; Thieno 2, 3 d pyrimidine

Indexed keywords

10 (2 HYDROXYETHYL) 5,6 DIHYDRONAPHTHOL[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11(10H) ONE; 10 (2 HYDROXYETHYL) 9 METHYL 5,6 DIHYDRONAPHTHOL[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11(10H) ONE; 10 (2 HYDROXYETHYSULFANYLL) 5,6 DIHYDRONAPHTHOL[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11(10H) ONE; 10 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSULFANYL) 5,6 DIHYDRONAPHTHOL[1',2':4,5]THIENO[2,3 D]PYRIMIDINE; 10 (ALPHA DEXTRO GLUCOPYRANOSULFANYL) 5,6 DIHYDRONAPHTHOL[1',2':4,5] THIENO[2,3 D]PYRIMIDINE; 10 (ALPHA DEXTRO GLUCOPYRANOSYL) 5,6 DIHYDRONAPHTHOL[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 11 (2 HYDROXYETHYSULFANYLL) 9 METHYL 5,6 DIHYDRONAPHTHOL[1',2':4,5] THIENO[2,3 D]PYRIMIDINE; 11 (2 METHOXY ETHYLSULFANYL) 5,6 DIHYDRONAPHTHOL[1',2':4,5]THIENO[2,3 D]PYRIMIDINE; 11 (2 METHOXY ETHYLSULFANYL) 9 METHYL 5,6 DIHYDRONAPHTHOL[1',2':4,5] THIENO[2,3 D]PYRIMIDINE; 2 CHLOROETHYL METHYL ETHER; 2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL BROMIDE; 5,6 DIHYDRONAPHTHOL[1',2':4,5]THIENO[2,3D]PYRIMIDINE 11(10H) THIONE; 9 METHYL 10 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSULFANYL) 5,6 DIHYDRONAPHTHOL[1',2':4,5]THIENO[2,3 D]PYRIMIDINE; 9 METHYL 10 (ALPHA DEXTRO GLUCOPYRANOSYL) 5,6 DIHYDROTHIONAPHTHO[1',2':4,5] THIENO[2,3 D]PYRIMIDINE; 9 METHYL 5,6 DIHYDRONAPHTHOL[1',2':4,5]THIENO[2,3D]PYRIMIDINE 11(10H) THIONE; ACICLOVIR; ANTIVIRUS AGENT; ETHER DERIVATIVE; GLUCOSE DERIVATIVE; NAPHTHOL DERIVATIVE; NUCLEOSIDE; THIENO[2,3 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; HEPATITIS A VIRUS; HERPES SIMPLEX VIRUS 1; HUMAN; HUMAN CELL; NONHUMAN;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; CRYSTALLOGRAPHY, X-RAY; DRUG EVALUATION, PRECLINICAL; HEPATITIS A VIRUS; HERPESVIRUS 1, HUMAN; HUMANS; MOLECULAR STRUCTURE; PYRIMIDINE NUCLEOSIDES; PYRIMIDINES;

HEPATITIS A VIRUS; HUMAN HERPESVIRUS 1;

EID: 33644810588     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770500377730     Document Type: Article

References (13)

1. Abdel-Megeid, F.M.E.; Hassan, N.A.; Zahran, M.A.; Rashad, A.E. Synthesis of 5,6-dihydronaphtho[1′,2′:4,5]thieuo[2,3-d]pyrimidines, 5,6-dihydronaphtho[1′,2′:4,5]thieno[3,2-e] [1,2,4]triazolo[1,5-c] pyrimidines and some of their nucleosides. Sulfur Lett. 1998, 21, 269-284.
2. Patil, V.D.; Wise, D.S.; Townsend, L.B. The synthesis thieno[2,3-d]pyrimidine nucleosides related to naturally occurring, nucleosides cytidine and uridine. J. Chem. Soc., Prekin Trans. 1980, 1, 1853-1858.
3. Patil, V.D.; Wise, D.S.; Wotring, L.L.; Bloomer, L.C.; Townsend, L.B. Synthesis and biological activity of a novel adenosine analog 3-β-D-ribofuranosylthieno[2,3-d]pyrimidin-4-one. J. Med. Chem. 1985, 28, 423-427.
4. Wamhoff, H.; Wambach, W.; Herrmann, S.; Jansen, M.; Bruhne, B. Heterocyclic β-enaminoesters, Studies on N-glycosides heterocyclic uracile. J. Prakt. Chem. 1994, 336, 1-15.
5. El-Barbary, A.A.; El-Brollosy, N.R.; Pedersen, E.B.; Nielsen, C. Synthesis of 5′-amino-and 5′-azido-2′,5′- dideoxynucleosides from thieno[2,3-d]pyrimidin-2,4(1H,3H)-dione. Monatsh. Chem. 1995, 126, 593-600.
6. Zeid, I.F.; Abdel-Rahman, A.A.H.; Abdel-Megeid, A.E.S.; El-Etrawy, A.S.H. Synthesis of new thiolated acyclonucleosides with potential anti-HBV activity. Nucleos. Nucleot. 1999, 18, 95-111.
7. Harden, M.R.; Jarvest, R.L.; Bacon, T.H.; Boyd, M.R. Synthesis and antiviral activity of 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]purines. J. Med. Chem. 1987, 30, 1636-1642.
8. Tanaka, H.; Baba, M.; Hayakawa, H.; Sakamaki, T.; Miyasaka, T.; Ubasawa, M.; Takashima, H.; Skiya, K.; Nitta, I.; Shigeta, S.; Walker, R.T.; Balzarini, J.; Declerq, E. A new class of HIV-1 specific 6-substituted acyclouridine derivatives: synthesis and anti-HIV-1 activity of 5- or 6-substituted analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). J. Med. Chem. 1991, 34, 349-357.
9. Cristescu, C.; Czobor, F. As-triazine derivatives with potential therapeutic action. XXVI. Synthesis of some 5-substituted-6-azauracil acyclonucleosides. Nucleos. Nucleot. 1998, 17, 1319-1324.
10. Shamroukh, A.H.; Rashad, A.E.; Sayed, H.H. Synthesis of some pyrazolo[3,4-d]pyrimidine derivatives for biological evaluation. Phosphorus, Sulfur, Silicon and Related Elements 2005, 180, 2347-2360.
11. Rashad, A.E.; Heikal, O.A.; El-Nazhawy, A.O.H.; Abdel-Megeid, F.M.E. Synthesis and isomerization of thienotriazolopyrimidine and thienotetrazolopyrimidine derivatives with potential anti-inflammatory activity. Heteroatom Chem. 2005, 16, 226-234.
12. Elgemeie, G.E.H.; Mansour, O.A.; Metwally, N.H. Synthesis and anti-HIC activity of different novel nonclassical nucleosides. Nucleos. Nucleot. 1999, 18, 113-123.
13. Farag, R.S.; Shalaby, A.S.; El-Baroty, G.A.; Ibrahim, N.A.; Ali, M.A.; Hassan, E.M. Synthesis and biological evaluation of the essential oils of different melaleuca species. Phytother. Res. 2004, 18, 30-37.