Synthesis of 4/5-deoxy-4/5-nucleobase derivatives of 3-O-methyl-D-chiro-inositol as potential antiviral agents

Chemistry and Biodiversity

Volumn 3, Issue 10, 2006, Pages 1126-1137

  Zhan, Tian Rong ^a   Ma, Yu Dao ^a   Fan, Pei Hong ^a   Ji, Mei ^a   Lou, Hong Xiang ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,6 TRI O BENZOYL 3 O METHYL 4,5 EPOXY DEXTRO CHIRO INOSITOL; 3 O METHYL 1,2:5,6 BIS O (1 METHYLETHYLIDENE) 4 [(METHYLSULFONYL)OXY] DEXTRO CHIRO INOSITOL; 3 O METHYL 1,2:5,6 BIS O (1 METHYLETHYLIDENE) DEXTRO CHIRO INOSITOL; 3 O METHYL 4 [(METHYLSULFONYL)OXY] DEXTRO CHIRO INOSITOL; 3 O METHYL 4,5 EPOXY DEXTRO CHIRO INOSITOL; 4 (ADENIN 9 YL) 4 DEOXY 3 O METHYL 1,2:5,6 BIS O (1 METHYLETHYLIDENE) DEXTRO CHIRO INOSITOL; 4 (ADENIN 9 YL) 4 DEOXY 3 O METHYL DEXTRO CHIRO INOSITOL; 4 (CYTOSIN 1 YL) 4 DEOXY 3 O METHYL 1,2:5,6 BIS O (1 METHYLETHYLIDENE) DEXTRO CHIRO INOSITOL; 4 (CYTOSIN 1 YL) 4 DEOXY 3 O METHYL DEXTRO CHIRO INOSITOL; 4 DEOXY 3 O METHYL 4 (THYMIN 1 YL) DEXTRO CHIRO INOSITOL; 4 DEOXY 3 O METHYL 4 (URACIL 1 YL) DEXTRO CHIRO INOSITOL; 4 DEOXY 4 (5 FLUOROCYTOSIN 1 YL) 3 O METHYL DEXTRO CHIRO INOSITOL; 4 DEOXY 4 (5 FLUOROURACIL 1 YL) 3 O METHYL DEXTRO CHIRO INOSITOL; 5 (ADENIN 9 YL) 4 DEOXY 3 O METHYL DEXTRO CHIRO INOSITOL; 5 (AMINO 6 CHLOROPURINE 9 YL) 5 DEOXY 3 O METHYL DEXTRO CHIRO INOSITOL; 5 (CYTOSIN 1 YL) 4 DEOXY 3 O METHYL DEXTRO CHIRO INOSITOL; 5 DEOXY 3 O METHYL 5 (THIOGUANIN 1 YL) DEXTRO CHIRO INOSITOL; 5 DEOXY 3 O METHYL 5 (THYMIN 1 YL) DEXTRO CHIRO INOSITOL; 5 DEOXY 5 (5 FLUOROCYTOSIN 1 YL) 3 O METHYL DEXTRO CHIRO INOSITOL; 5 DEOXY 5 (5 FLUOROURACIL 1 YL) 3 O METHYL DEXTRO CHIRO INOSITOL; 5 DEOXY 5 (6 GUANIN 9 YL) 3 O METHYL DEXTRO CHIRO INOSITOL; 5' DEOXY 3 O METHYL 5 (URACIL 1 YL) DEXTRO CHIRO INOSITOL; ANTIVIRUS AGENT; ELVUCITABINE; NUCLEIC ACID BASE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; BLADDER CANCER; CANCER CELL CULTURE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; INHIBITION KINETICS; LUNG CANCER; NONHUMAN;

ANTIVIRAL AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; CYTOPATHOGENIC EFFECT, VIRAL; HUMANS; INOSITOL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN HERPESVIRUS 1; HUMAN HERPESVIRUS 2; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 33750606222     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200690114     Document Type: Article

References (33)

1. M. J. Kaneko, Synth. Org. Chem. Jpn. 1991, 49, 989.
2. R. E. Boehme, A. D. Borthwick, P. G. Wyatt, Annu. Rep. Med. Chem. 1994, 29, 145.
3. J. Saunders, J. M. Cameron, Med. Res. Rev. 1995,15, 497
4. V Marquez, Adv. Antiviral Drug Des. 1996, 2, 46.
5. L. A. Agrofoglio, F. Amblard, S. P. Nolan, S. Charamon, I. Gillaizeau, T. A. Zevaco, P. Guenot, Tetrahedron 2004, 60, 8397
6. D. R. Borcherding, S. A. Scholtz, R. T. Borchardt, J. Org. Chem. 1987, 52, 5457
7. S. J. Boyer, J. W. Leahy, J. Org. Chem. 1997, 62, 3976.
8. J. H. Arango, A. Geer, J. Rodriguez, P. E. Young, P. Scheiner, Nucleosides Nucleotides 1993, 12, 773
9. A. Rosenquist, I. Kvarnstrom, B. Classon, B. Samuelsson, J. Org. Chem. 1996, 61, 6282
10. I. Kitagawa, B. C. Cha, T. Nakae, Y. Okaichi, Y. Takinami, M. Yoshikawa, Chem. Pharm. Bull. 1989, 37, 542
11. S. N. Mikhailov, N. Blaton, J. Rozenski, J. Balzarini, E. De Clercq, P. Herdewijn, Nucleosides Nucleotides 1996, 15, 867.
12. Y. Maurinsh, J. Schraml, H. De Winter, N. Blaton, O. Peeters, E. Lescrinier, J. Rozenski, A. Van Aerschot, E. De Clercq, R. Busson, P. Herdewijn, J. Org. Chem. 1997, 62, 2861
13. I. Verheggen, A. Van Aerschot, S. Toppet, R. Snoeck, G. Jannsen, J. Balzarini, E. De Clereq, P. Herdewijn, J. Med. Chem. 1993, 36, 2033
14. I. Verheggen, A. Van Aerschot, L. Van Meervelt, J. Rozenski, L. Wiebe, R. Snoeck, G. Andrei, J. Balzarini, P. Claes, E. De Clercq, P. Herdewijn, J. Med. Chem. 1995, 38, 826.
15. J. Wang, R. Busson, N. Blaton, J. Rozenski, P. Herdewijn, J. Org. Chem. 1998, 63, 3051
16. J. Wang, M. Froeyen, C. Hendrix, G. Andrei, R. Snoeck, E. De Clercq, P. Herdewijn, J. Med. Chem. 2000, 43, 736.
17. J. G. Streeter, Crop Science 2001, 41, 1985
18. T. M. Kuo, C. A. Lowell, T. C. Nelsen, Phytochemistry 1997, 45, 29
19. R. L. Bieleski, New Zeal. J. Bot. 1994, 32, 73.
20. J. Larner, J. D. Price, D. Heimark, L. Smith, G. Rule, T. Piccariello, M. C. Fonteles, C. Pontes, D. Vale, L. Huang, J. Med. Chem. 2003, 46, 3283.
21. L. A. Agrofoglio, E. Suhas, A. Farese, R. Condom, S. R. Challand, R. Earl, R. Guedj, Tetrahedron 1994, 50, 10611
22. A. D. Borthwick, K. Biggadike, Tetrahedron 1992, 48, 571
23. M. T. Crimmins, Tetrahedron 1998, 54, 9229.
24. A. P. Kozikowski, A. H. Fauq, G. Powis, D. C. Melder, J. Am. Chem. Soc. 1990, 112, 4528.
25. H. O. Kim, S. J. Yoo, H. S. Ahn, W. J. Choi, H. R. Moon, K. M. Lee, M. W. Chun, L. S. Jeong, Bioorg. Med. Chem. Lett. 2004, 14, 2091
26. H. R. Moon, H. J. Lee, K. R. Kim, K. M. Lee, S. K. Lee, H. O. Kim, M. W. Chun, L. S. Jeong, Bioorg. Med. Chem. Lett. 2004, 14, 5641.
27. A. F. Cunningham, E. P. Kündig, J. Org. Chem. 1988, 53, 1823.
28. Z. Lei, J. M. Min, L. H. Zhang, Tetrahedron: Asymmetry 2000, 11, 2899.
29. C. H. Behrens, S. Y. KO, K. B. Sharpless, F. J. Walker, J. Org. Chem. 1985, 50, 5687.
30. Y. Chong, G. Gumina, C. K. Chu, Tetrahedron: Asymmetry 2000, 11, 4853.
31. J. Wachtmeister, B. Classon, B. Samuelsson, Tetrahedron 1995, 51, 9858.
32. E. De Clereq, A. Hóly, I. Rosenberg, T. Sakuma, J. Balzarini, P. C. Maudgal, Nature 1986, 141, 464.
33. J. Carmichael, A. F. DeGraff Gazdar, Cancer Res. 1987, 47, 936.