Synthesis of N-1-alkylated 6-benzyluracil-5-carboxylic esters as potential non-nucleoside reverse transcriptase inhibitors

Synthesis

Volumn , Issue 11, 2004, Pages 1874-1878

  Larsen, Janus S ^a   Pedersen, Erik B ^a   Nielsen, Claus ^b  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^b STATENS SERUM INSTITUT   (Denmark)

Author keywords

Emivirine; HIV 1; HSV; Non nucleoside reverse transcriptase inhibitors; Uracil 5 carboxylic esters

Indexed keywords

ETHERS; METHANE; SYNTHESIS (CHEMICAL);

DEALKYLATION; ISOCYANATE;

ESTERS;

1 ALLYLOXYMETHYL 6 BENZYL 5 ETHOXYCARBONYLURACIL; 3 OXO 4 PHENYLBUTYRATE DERIVATIVE; 5 ALLYLOXYCARBONYL 6 BENZYL 1 ETHOXYMETHYLURACIL; 5 ALLYLOXYCARBONYL 6 BENZYL 1 ISOPROPYLURACIL; 6 BENZYL 5 ALLYLOXYCARBONYL 1 (4 METHOXYPHENYLMETHYL)URACIL; 6 BENZYL 5 ALLYLOXYCARBONYLURACIL; 6 BENZYL 5 ETHOXYCARBONYL 1 (4 METHOXYPHENYLMETHYL)URACIL; 6 BENZYL 5 ETHOXYCARBONYL 1 (4 PYRIDYLMETHYL)URACIL; 6 BENZYL 5 ETHOXYCARBONYL 1 (N,N DIMETHYLAMINOETHYL)URACIL; 6 BENZYL 5 ETHOXYCARBONYL 1 CYCLOPENTYLMETHYLURACIL; 6 BENZYL 5 ETHOXYCARBONYL 1 ETHOXYMETHYLURACIL; 6 BENZYL 5 ETHOXYCARBONYL 1 ISOPROPYLURACIL; 6 BENZYL 5 ETHOXYCARBONYL 1 MORPHOLINOURACIL; 6 BENZYL 5 ETHOXYCARBONYLURACIL; 6 BENZYLURACIL 5 CARBOXYLIC ESTER DERIVATIVE; CHLOROCARBONYLISOCYANATE; ISOCYANIC ACID DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DEALKYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 4043100648     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829137     Document Type: Article

References (29)

1. Merluzzi, V. J.; Hargrave, K. D.; Labadia, M.; Grozinger, K.; Skoog, M.; Wu, J. C.; Shih, C. K.; Eckner, K.; Hattox, S. Science 1990, 250, 1411.
2. Hargrave, K. D.; Proudfoot, J. R.; Grozinger, K. G.; Cullen, E.; Kapadia, S. R.; Patel, U. R.; Fuchs, V. U.; Mauldin, S. C.; Vitous, J.; Behnke, M. L. J. Med. Chem. 1991, 34, 2231.
3. Klunder, J. M.; Hargrave, K. D.; West, M.; Cullen, E.; Pal, K.; Behnke, M. L.; Kapadia, S. R.; McNeil, D. W.; Wu, J. C.; Chow, G. C. J. Med. Chem. 1992, 35, 1887.
4. Proudfoot, J. R.; Patel, U. R.; Kapadia, S. R.; Hargrave, K. D. J. Med. Chem. 1995, 38, 1406.
5. Romero, D. L.; Busso, M.; Tan, C. K.; Reusser, F.; Palmer, J. R.; Poppe, S. M.; Aristoff, P. A.; Downey, K. M.; So, A. G. Proc. Natl. Acad. of Sci., U.S.A. 1991, 88, 8806.
6. Romero, D. L.; Morge, R. A.; Biles, C.; Berrios-Pena, N.; May, P. D.; Palmer, J. R.; Johnson, P. D.; Smith, H. W.; Busso, M.; Tan, C.-K.; Vorman, R. L.; Reusser, F.; Althaus, I. W.; Downey, K. M.; So, A. G.; Resnick, L.; Tarpley, W. G.; Aristoff, P. A. J. Med. Chem. 1994, 37, 999.
7. Romero, D. L.; Olmsted, R. A.; Poel, T. J.; Morge, R. A.; Biles, C.; Keiser, B. J.; Kopta, L. A.; Friis, J. M.; Hosley, J. D. J. Med. Chem. 1996, 39, 3769.
8. Young, S. D.; Britcher, S. F.; Tran, L. O.; Payne, L. S.; Lumma, W. C.; Lyle, T. A.; Huff, J. R.; Anderson, P. S.; Olsen, D. B. Antimicrob. Agents Chemother. 1995, 39, 2602.
9. Young, S. D.; Britcher, S. F.; Payne, L. S.; Tran, L. O.; Lumma, W. C. Jr. WO Pat., 9520389, 1995.
10. Ventura, M.; Tarrago-Litvak, L.; Dolle, V.; Nguyen, C. H.; Legraverend, M.; Fleury, H. J. A.; Litvak, S. Arch. Virol. 1999, 144, 513.
11. Dolle, V.; Aubertin, A. M.; Ludwig, O.; Nguyen, C. H.; Bisagni, E.; Legraverend, M. Bioorg. Med. Chem. Lett. 1996, 6, 173.
12. Dolle, V.; Fan, E.; Nguyen, C. H.; Aubertin, A. M.; Kim, A.; Andreola, M. L.; Jamieson, G.; Tarrago-Litvak, L.; Bisagni, E. J. Med. Chem. 1995, 38, 4679.
13. Larsen, J. S.; Abdel Aal, M. T.; Pedersen, E. B. J. Heterocycl. Chem. 2001, 38, 1.
14. Larsen, J. S.; Christensen, L.; Ludvig, G.; Jørgensen, P. T.; Pedersen, E. B.; Nielsen, C. J. Chem. Soc., Perkin Trans. 1 2000, 1, 3035.
15. Jaeger, G.; Hagemann, H.; Findeisen, K.; Von Konig, A.; Poot, A.; Van Beseuw, J. F. Ger. Pat., DE 2520956, 1975; A1.
16. Hagemann, H.; Ley, K. Ger. Pat., DE 1959705, 1971.
17. Ley, K.; Aichinger, G.; Hagemann, H. Ger. Pat., DE 2142317, 1973.
18. Ley, K.; Aichinger, G.; Botta, A. Ger. Pat., DE 2126148, 1972.
19. Grohe, K.; Heitzer, H. Liebigs Ann. Chem. 1982, 5, 894.
20. Mottet, C.; Hamelin, O.; Garavel, G.; Depres, J. P.; Greene, A. E. J. Org. Chem. 1999, 64, 1380.
21. Gribble, G. W.; Switzer, F. L.; Soll, R. M. J. Org. Chem. 1988, 53, 3164.
22. Yoda, H.; Nakajima, T.; Takabe, K. Synlett 1997, 911.
23. Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 16, 2405.
24. Renard, A.; Kotera, M.; Lhomme, J. Tetrahedron Lett. 1998, 39, 3129.
25. Funke, C.; Es-Sayed, M.; de Meijere, A. Org. Lett. 2000, 2, 4249.
26. Lohse, O.; Beutler, U.; Funfschilling, P.; Furet, P.; France, J.; Kaufmann, D.; Penn, G.; Zaugg, W. Tetrahedron Lett. 2001, 42, 385.
27. Botta, M.; Summa, V.; Saladino, R.; Nicoletti, R. Synth. Commun. 1991, 21, 2181.
28. Holschbach, M. H.; Fein, T.; Krummeich, C.; Lewis, R. G.; Wutz, W.; Schwabe, U.; Unterlugauer, D.; Olsson, R. A. J. Med. Chem. 1998, 41, 555.
29. Tucker, T. J.; Lyle, T. A.; Wiscount, C. M.; Britcher, S. F.; Young, S. D.; Sanders, W. M.; Lumma, W. C.; Goldman, M. E.; O'Brien, J. A. J. Med. Chem. 1994, 37, 2437.