Synthesis and biological evaluation of the L-enantiomer of 2′-deoxy-5-ethyl-4′-thiouridine

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 8, 1996, Pages 991-994

  Selwood, David L ^a   Carter, Keith ^b,c   Young, Robert J ^b,c   Jandu, Karamjit S ^b,c  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b WELLCOME RESEARCH LABORATORIES   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OXY;

2' DEOXY 5 ETHYL 4' THIOURIDINE; ANTIVIRUS AGENT; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOMEGALOVIRUS; DRUG SYNTHESIS; ENANTIOMER; HERPES SIMPLEX VIRUS 2; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS; NONHUMAN; VARICELLA ZOSTER VIRUS;

EID: 0029965793     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00161-8     Document Type: Article

References (17)

1. 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. Synthesis and anti-herpes virus activity of 2′-deoxy-4′-thiopyrimidine nucleosides. J. Med. Chem. 1996, 39, 789-795.
2. Jandu, K.S.; Selwood, D. L.; J. Org. Chem. 1995, 60, 5170-5173.
3. Secrist, J.A.; Tiwari, K.N.; Riordan, J.M.; Montgomery, J.A. J. Med. Chem. 1991, 34, 2361-2366.
4. Coates, J. A. V.; Cammack, N.; Jenkinson, H.J. ; Mutton, I. M.; Pearson, .B. A.; Storer, R.; Camerson, J. M.; Penn, C. R.; Antimicrob. Agents Chemother. 1992, 36, 202-205.
5. Furman, P. A.; Davis, M.; Liotta, D. C.; Paff, M.; Frick, L. W.; Nelson, D. J.; Dornsife, R. E.; Wurster, J. A.; Wilson, L. J.; Fyfe, J. A. ; Tuttle, J. V.; Miller, W. H.; Condreay, L.; Averett, D. R.; Schinazi, R. F.; Painter, G. R.; Antimicrob. Agents Chemother. 1992, 36, 2686-2692.
6. Young, R. J.; Shaw-Ponter, S.; Thomson, J. B.; Miller, J. A.; Cumming, J. G.; Pugh, A. W.; Rider, P.; Bioorg. Med. Chem. Lett. 1995, 5, 2599-2604.
7. Grove, K. L.; Guo, X.; Liu, S-H.; Gao, Z.; Chu, C. K.; Cheng, Y-C.; Cancer Research 1995, 55, 3008-3011.
8. Schinazi, R. F.; Gosselin, G.; Faraj, A.; Korba, B. E.; Liotta, D. C.; Chu, C. K.; Mathe, C.; Imbach, J-L; Sommadossi, J-P.; Antimicrob. Agents Chemother. 1994, 38, 2172-2174.
9. Uenishi, J.; Takahashi, K.; Motoyama, M.; Akashi, H.; Sasaki, T.; Nucleosides and Nucleotides 1994, 13 (6 & 7), 1347.
10. Shaw-Ponter, S.; Rider, P.; Young, R.J.; Tetrahedron Lett. 1996, 37 (12), 1867.
11. Tamaru, Y.; Mitzutani, M; Furukawa, S.; Kawamura, S.; Yoshida, Z.; Yanagi, K.; Minobe, M.; J. Amer. Chem. Soc. 1984, 106, 1079-1085.
12. Chamberlain, A. R.; Dezube, M.; Dussault, P.; Tetrahedron Lett. 1981, 22, 4611-4614.
13. Miwa, T.; Narasaka, K.; Mukaiyama, T.; Chem. Lett. 1984, 1093-1096.
14. Hall, L. D.; Hough, L.; Prichard R. A.; J. Chem. Soc. 1961, 1537-1545.
15. Rowell, R. M.; Whistler R. L.; J. Org. Chem. 1966, 31, 1514-1516.
16. Separation of the racemic α/β anomer mixture was achieved on a Chiralcel OJ analytical column (J.T. Baker Ltd.) using hexane / EtOH as eluent. The identity of the components was established by co-injection with authentic D isomers and analysis of the nmr spectra. Analytical data were as reported for compound 1 (ref 2).
17. see ref 1 for details of the anti-viral assays employed