Synthesis and potent anti-HIV activity of L-2′-3′-Didehydro-2′-3′-dideoxy-2′-fluoro- 4′-thiocytidine

Organic Letters

Volumn 4, Issue 2, 2002, Pages 305-307

  Choi, Yongseok ^a   Choo, Hyunah ^a   Chong, Youhoon ^a   Lee, Sookwang ^a   Olgen, Sureyya ^a   Schinazi, Raymond F ^b   Chu, Chung K ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; CYTIDINE; DRUG DERIVATIVE; L 2',3' DIDEHYDRO 2',3' DIDEOXY 2' FLUORO 4' THIOCYTIDINE; L-2',3'-DIDEHYDRO-2',3'-DIDEOXY-2'-FLUORO-4'-THIOCYTIDINE; NUCLEOSIDE;

ARTICLE; CELL LINE; DRUG EFFECT; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; MONONUCLEAR CELL; SYNTHESIS;

ANTI-HIV AGENTS; CELL LINE; CYTIDINE; DIDEOXYNUCLEOSIDES; HIV-1; HUMANS; INHIBITORY CONCENTRATION 50; LEUKOCYTES, MONONUCLEAR; THIONUCLEOSIDES;

EID: 0037165411     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0171665     Document Type: Article

References (14)

1. Mitsuya, H.; Broder, S. Proc. Natl. Acad. Sci. USA. 1986, 83, 1911-1915.
2. Kim, H. O.; Schinazi, R. F.; Nampalli, S.; Shanmuganathan, K.; Cannon, D. L.; Alves, A. J.; Jeong, L. S.; Beach, J. W.; Chu, C. K. J. Med. Chem. 1993, 36, 30-37.
3. (a) Schinazi, R. F.; Chu, C. K.; Peck, A.; McMillan, A.; Mathis, R.; Cannon, D.; Jeong, L. S.; Beach, J. W.; Choi, W. B.; Yeola, S.; Liotta, D. C. Antimicrob. Agents Chemother. 1992, 36, 672-676.
4. (b) Coates, J. A. V.; Cammack, N.; Jenkinson, H. J.; Mutton, I. M.; Pearson, B. A.; Storer, R.; Cameron, J. M.; Penn, C. R. Antimicrob. Agents Chemother. 1992, 36, 202-205.
5. Lin, T. S.; Schinazi, R. F.; Prusoff, W. H. Biochem. Phannacol. 1987, 36, 2713-2718.
6. Schinazi, R. F.; McMillan, A.; Cannon, D.; Mathis, R.; Lloyd, R. M.; Peck, A.; Sommadossi, J. P.; St. Clair, M.; Wilson, J.; Furman, P. A.; Painter, G.; Choi, W. B.; Liotta, D. C. Antimicrob. Agents Chemother. 1992, 36, 2423-2431.
7. Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Med. Chem. 1991, 34, 2782-2786.
8. Secrist, J. A., III; Tiwari, K. N.; Riordan, J. M.; Mongamery, J. A. J. Med. Chem. 1991, 34, 2361-2366.
9. Secrist, J. A., III; Riggs, R. M.; Tiwari, K. N.; Mongamery, J. A. J. Med. Chem. 1992, 35, 533-538.
10. Mann, J.; Tench, A. J.; Weymouth-Wilson, A.; Shaw-Ponter, S.; Young, R. J. J. Chem. Soc., Perkin Trans, 1 1995, 677-681.
11. Young, R. J.; Shaw-Ponter, S.; Thomson, J. B.; Miller, J. A.; Gumming, J. G.; Pugh, A. W.; Rider, P. Bioorg. Med. Chem. Lett. 1995, 5, 2599-2604.
12. Lee, K.; Choi, Y.; Gullen, E.; Schlueter-Wirtz, S. Schinazi, R. F.; Cheng, Y. C.; Chu, C. K. J. Med. Chem. 1999, 42, 1320-1328.
13. Gumina, G.; Chong, Y.; Choi, Y.; Chu, C. K. Org. Lett. 2000, 2, 1229-1231.
14. 2: C, 41.39; H, 3.97; N, 15.54; S, 11.86. Found: C, 41.15; H, 4.10; N, 15.55; S, 11.82.