A new DNA building block, 4′-selenothymidine: Synthesis and modification to 4′-seleno-AZT as a potential anti-HIV agent

Organic Letters

Volumn 12, Issue 10, 2010, Pages 2242-2245

  Alexander, Varughese ^a   Choi, Won Jun ^a   Chun, Jeongha ^a   Kim, Hea Ok ^a   Jeon, Ji Hye ^a   Tosh, Dilip K ^a   Lee, Hyuk Woo ^a   Chandra, Girish ^a   Choi, Jungwon ^b   Jeong, Lak Shin ^a  

^a Ewha Womans University   (South Korea)

^b Suwon University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

4' SELENO AZT; 4' SELENOTHYMIDINE; 4'-SELENO-AZT; 4'-SELENOTHYMIDINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DNA; DRUG DERIVATIVE; ORGANOSELENIUM DERIVATIVE; THYMIDINE; ZIDOVUDINE;

ARTICLE; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECT; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; MICROBIOLOGICAL EXAMINATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTI-HIV AGENTS; CELL LINE; CRYSTALLOGRAPHY, X-RAY; DNA; HIV-1; HUMANS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOSELENIUM COMPOUNDS; THYMIDINE; ZIDOVUDINE;

EID: 77952376585     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1005906     Document Type: Article

References (27)

1. Breaker, R. R. Nature 2004, 432, 838-845
2. Uenishi, J.; Takahashi, K.; Motoyama, M.; Akashi, H.; Sasaki, T. Nucleosides Nucleotides 1994, 13, 1347-1361
3. Tiwari, K. N.; Montgomery, J. A.; Secrist, J. A., III Nucleosides Nucleotides 1993, 12, 841-846
4. Rahim, S. G.; Trivedi, N.; Bogunovic-Batchelor, M. V.; Hardy, G. W.; Mills, G.; Selway, J. W. T.; Snowden, W.; Littler, E.; Coe, P. L.; Basnak, I.; Whale, R. F.; Walker, R. T. J. Med. Chem. 1996, 39, 789-795
5. Secrist, J. A., III; Tiwari, K. N.; Riordan, J. M.; Montgomery, J. A. J. Med. Chem. 1991, 34, 2361-2366
6. Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Med. Chem. 1991, 34, 2782-2786
7. Uenishi, J.; Takahashi, K.; Motoyama, M.; Akashi, H. Chem. Lett. 1993, 255-256
8. Gunaga, P.; Moon, H. R.; Choi, W. J.; Shin, D. H.; Park, J. G.; Jeong, L. S. Curr. Med. Chem. 2004, 11, 2585-2637
9. Van Draanen, N. A.; Freeman, G. A.; Short, S. A.; Harvey, R.; Jansen, R.; Szczech, G.; Koszalka, G. W. J. Med. Chem. 1996, 39, 538-542
10. Altona, C.; Sundaranlingam, M. J. Am. Chem. Soc. 1972, 94, 8205
11. Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St. Clair, M. H.; Lehrmann, S. N.; Gallo, R. C.; Bolognesi, D.; Barry, D. W.; Broder, S. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7096-7100
12. Arts, E. J.; Wainberg, M. A. Antimicrob. Agents Chemother. 1996, 40, 527-540
13. Styrt, B. A.; Piazza-Hepp, T. D.; Chikami, G. K. Antiviral Res. 1996, 31, 121-135
14. Chu, C. K.; Schinazi, R. F.; Ahn, M. K.; Ullas, G. V.; Gu, Z. P. J. Med. Chem. 1989, 32, 612-617
15. Zhu, Z.; Schinazi, R. F.; Chu, C. K.; Williams, G. J.; Colby, C. B.; Sommadossi, J. P. Mol. Pharmacol. 1990, 38, 929-938
16. Jeong, L. S.; Tosh, D. K.; Kim, H. O.; Wang, T.; Hou, X.; Yun, H. S.; Kwon, Y.; Lee, S. K.; Choi, J.; Zhao, L. X. Org. Lett. 2008, 10, 209-212
17. Jayakanthan, K.; Johnston, B. D.; Pinto, B. M. Carbohydr. Res. 2008, 343, 1790-1800
18. Watts, J. K.; Johnston, B. D.; Jayakanthan, K.; Wahba, A. S.; Pinto, B. M.; Damha, M. J. J. Am. Chem. Soc. 2008, 130, 8578-8579
19. Jeong, L. S.; Tosh, D. K.; Choi, W. J.; Lee, S. K.; Kang, Y.-J.; Choi, S.; Lee, J. H.; Lee, H.; Lee, H. W.; Kim, H. O. J. Med. Chem. 2009, 52, 5303-5306
20. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 16, 1574-1585
21. Tosh, D. K.; Choi, W. J.; Kim, H. O.; Lee, Y.; Pal, S.; Hou, X.; Choi, J.; Choi, S.; Jeong, L. S. J. Org. Chem. 2008, 73, 4259-4262
22. Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 6125-6126
23. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413-1432
24. Naonori, I.; Daisuke, K.; Noriaki, M.; Akira, M. J. Org. Chem. 2005, 70, 8597-8600
25. Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742-5743
26. -3. Flack x parameter = 0.025(9). Further details of the crystal structure investigation(s) may be obtained from the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge, CB2 1EZ (U.K.); Tel: (+44)1223-336-408, Fax: (+44)1223-336-033, e-mail: deposit@ccdc.cam.ac.uk) on quoting the depository no. CCDC-761848.
27. Chen, B.-C.; Quinlan, S. L.; Reid, J. G. Tetrahedron Lett. 1995, 36, 7961-7964