Synthesis and antiviral evaluation of isatin ribonucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 21, Issue 11-12, 2002, Pages 825-835

  De Oliveira, Mara R P ^a   Torres, José C ^a   Garden, Simon J ^a   Dos Santos, Carla Veronica B ^a   Rocha Alves, Thatyana ^a   Pinto, Angelo C ^a   Pereira, Helena de S ^a   Leão Ferreira, Luiz Roberto ^a   Moussatché, Nissin ^a   Frugulhetti, Izabel Christina de P P ^a   Ferreira, Vitor F ^a   De Souza, Maria Cecilia B V ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

4,6 DIBROMO 2,3 DIHYDRO 1 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL)INDOLE 2,3 DIONE; ISATIN DERIVATIVE; ISATIN RIBONUCLEOSIDE; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 1; MELTING POINT; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TISSUE CULTURE; VERO CELL; VIRUS INHIBITION;

ANTIVIRAL AGENTS; CELL LINE; DRUG DESIGN; HERPESVIRUS 1, HUMAN; HIV-1 REVERSE TRANSCRIPTASE; ISATIN; MOLECULAR STRUCTURE; RIBONUCLEOSIDES;

ANIMALIA; HUMAN HERPESVIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; SIMPLEXVIRUS; STAPHYLOCOCCUS PHAGE 3A;

EID: 0036916434     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120016510     Document Type: Article

References (25)

1. Kolb, V.M. Novel and unusual nucleosides as drugs. Prog. Drug Res. 1997, 48, 195-232.
2. da Silva, J.F.M.; Garden, S.J.; Pinto, A.C. The chemistry of isatins: A review from 1975 to 1999. J. Braz. Chem. Soc. 2001, 12 (3), 273-286.
3. Medvedev, A.E.; Clow, A.; Sandler, M.; Glover, V. Isatin: A link between natriuretic peptides and monoamines. Biochem.-Pharmacol. 1996, 52 (3), 385-391.
4. (a) Atta-Ur-Rehman; Ijaz, A.S.; Choudhary, M.I.; Amtul, Z.; Atta-Ur-Rahman. New Isatin Derivatives and Their Antimicrobial Activity. J. Chem. Soc. Pakistan, 1997, 19 (3), 230-236;
5. (b) Pandeya, S.N.; Sriram, D.; Nath, G.; de Clercq, E. Synthesis, antibacterial; antifungal and anti HIV-activities of norfloxacin mannich bases. Eur. J. Med. Chem. 2000, 35 (2), 249-255;
6. (c) Pandeya, s.N.; sriram, d.; Nath, G.; de Clercq, E. Synthesis, antibacterial, antifungal and anti HIV activity of schiff and mannich bases derived from isatin derivatives and n-[4-(4′-chlorophenyl)thiazol-2-yl]thiosemicarbazide. Eur. J. Pharm. Sci. 1999, 9, 25-31.
7. Teitz, Y.; Barko, N.; Abramoff, M.; Ronen, D. Relationships between structure and antiretroviral activity of thiosemicarbazone derivatives. Chemotherapy 1994, 40 (3), 195-200.
8. (a) Yartseva, I.V.; Éktova, L.V.; Preobrazhenskaya, M.N. 1-Ribosylisatins. Bioorg. Khim. 1975, 1 (2), 189-194;
9. (b) Yartseva, I.V.; Éktova, L.V.; Preobrazhenskaya, M.N.; Lesnaya, N.A.; Yavorskaya, N.P.; Platonova, G.N.; Sofyina, Z.P. 1-Glucosylisatins and their biological activities on animals with transplantable tumors and in vitro. Bioorg. Khim. 1975, 1 (11), 1589-1592;
10. (c) Yartseva, I.V.; Éktova, L.V.; Sakharova, V.I.; Dobrynin, Y.V.; Yavorskaya, N.P.; Nikolaeva, T.G.; Sofina, Z.P.; Preobrazhenskaya, M.N. Synthesis and study of 1-glycosylations. Zh. Org. Khim. 1977, 13 (8), 1743-1749.
11. Dobrynin, Y.V.; Nikolaeva, T.G.; Shkrgova, A.D.; Lesnaya, N.A.; Peretolchina, N.M.; Sofyina, Z.P.; Éktova, L.V.; Tolkachev, V.N.; Preobrazhenskaya, M.N. Structure-cyto-toxic activity relationship in 1-glycosylisatins 3-derivatives. Khim.-Farm. Zh. 1984, 18 (12), 1440-1444.
12. Éktova, L.V.; Tolkachev, V.N.; Yartseva, I.V.; Paramonova, T.D.; Lesnaya, N.A.; Sofyina, Z.P.; Marennikova, S.S; Chekunova, E.V.; Preobrazhenskaya, M.N. Synthesis and study of the derivatives of 5-bromo-glycosylisatins, 6-nitro-1-glycosylisatins and 5-bromo-6- nitro-1-glycosylisatins. Khim.-Farm. Zh. 1984, 7, 776-785.
13. Preobrazhenskaya, M.N.; Yartseva, I.V.; Ektova, L.V. 1-Beta-D-glucopyranosides of isatin and methylisatins. Dokl. Akad. Nauk SSSR 1974, 215 (4), 873-876.
14. (a) Garden S.J.; Torres, J.C.; Ferreira, A.A.; Silva, R.B.; Pinto, A.C. A modified sandmeyer methodology and the synthesis of (±) convolutamydine A. Tetrahedron Lett. 1997, 38 (9), 1501-1504 and references cited therein;
15. (b) Garden, S.J.; Torres, J.C.; Melo, S.C.D.; Lima, A.S.; Pinto, A.C.; Lima, E.L.S. Aromatic iodination in aqueous solution. A new base of life for aqueous potassium dichloroiodate. Tetrahedron Lett. 2001, 42 (11), 2089-2092;
16. (c) Torres, J.C.; Garden, S.J.; Pinto, A.C.J. An investigation of a palladium catalysed biaryl synthesis of pyrrolophenanthidine derivatives: Extension of heck reaction. J. Braz. Chem. Soc. 2000, 11 (5), 441-446.
17. Garden S.J.; Torres, J.C.; Silva L.E.; Pinto, A.C. A convenient methodology for the n-alkylkation of isatin compounds. Synth. Commun. 1998, 28 (9), 1679-1689.
18. (a) Niedballa, U.; Vorbrüeggen, H. A general synthesis of N-glycosides. I. Synthesis of pyrimidine nucleosides J. Org. Chem. 1974, 39 (25), 3654-3660;
19. (b) Niedballa, U.; Vorbrüeggen, H. On the mechanism of the stannic chloride catalysed silyl Hilbert-Johnson reaction. J. Org. Chem. 1976, 41 (12), 2084-2086.
20. (a) da Matta, A.D.; Bernardino, A.M.R.; Romeiro, G.A.; de Oliveira, M.R.P.; de Souza, M.C.B.V.; Ferreira, V.F. Nucleosides having quinolone derivatives as nitrogenated bases: Regiospecific and stereospecific ribosylation of 3-carbethoxy-1,4-dihydro-4-oxoquinolines. Nucleosides & Nucleotides 1996, 15 (4), 889-898;
21. (b) da Matta, A.D.; dos Santos, C.V.B.; Pereira, H.S.; Frugulhetti, I.C.P.P.; de Oliveira, M.R.P.; de Souza M.C.B.V.; Moussatché, N.; Ferreira, V.F. Synthesis of novel nucleosides of 4-oxoquinoline-3-carboxylic acid analogues. Heteroatom Chemistry 1999, 10 (3), 197-202.
22. Vorbrüeggen, H.; Krolikiewicz, K.; Bennua, B. Nucleoside syntheses, XXII. Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem. Ber. 1981, 114 (4), 1234-1255.
23. Rosemeyer, H.; Tóth, G.; Seela, F. Assignment of anomeric configuration of D-ribonucleosides, arabinonucleosides, 2′-desoxyribonucleosides by NOE difference spectroscopy. Nucleosides & Nucleotides 1989, 8, 587-597.
24. Reed L.J.; Muench, M.A. A simple method of estimating fifty percent end points. Am. J. Hyg. 1938, 27, 493-497.
25. Hizi, A.; Mc Gill, C.; Hughes, H. Expression of soluble, enzymatically active human immunodeficiency virus reverse transcriptase in escherichia coli and analysis o mutants. Proc. Natl. Acad. Sci. USA 1988, 85, 1218-1222.