Design and synthesis of bioactive adamantane spiro heterocycles

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 15, 2007, Pages 4358-4362

  Kolocouris, Nicolas ^a   Zoidis, Grigoris ^a   Foscolos, George B ^a   Fytas, George ^a   Prathalingham, S Radhika ^b   Kelly, John M ^b   Naesens, Lieve ^c   De Clercq, Erik ^c  

^a UNIVERSITY OF ATHENS   (Greece)

^b LONDON SCHOOL OF HYGIENE AND TROPICAL MEDICINE   (United Kingdom)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Adamantane spiro heterocycles; Anti influenza A virus agent; H3N2; NMR; Rimantadine; Trypanocidal activity

Indexed keywords

ADAMANTANE; BARBITURIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; PIPERIDINE; RIBAVIRIN; RIMANTADINE; SPIRO[AZETIDINE 2,2' ADAMANTANE DERIVATIVE]; SPIRO[AZETIDINE 3,2' ADAMANTANE]; SPIRO[AZIRIDINE 2,2' ADAMANTANE DERIVATIVE]; SPIRO[PIPERIDINE 4,2' ADAMANTANE DERIVATIVE]; UNCLASSIFIED DRUG;

ARTICLE; BLOOD FLOW; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; INFLUENZA VIRUS A; NONHUMAN; TRYPANOSOMA BRUCEI;

ADAMANTANE; ANIMALS; ANTIPROTOZOAL AGENTS; ANTIVIRAL AGENTS; HETEROCYCLIC COMPOUNDS; INFLUENZA A VIRUS; LEISHMANIA; TRYPANOSOMA;

INFLUENZA A VIRUS; TRYPANOSOMA BRUCEI;

EID: 34347400782     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.04.108     Document Type: Article

References (32)

1. The Lancet Infectious Diseases. Lancet Infect. Dis. 2007, 7, 175.
2. Ferguson N.M., Cummings D.A.T., Cauchemez S., Fraser C., Riley S., Meeyai A., Iamsirithaworn S., and Burke D.S. Nature 437 (2005) 209
3. Ferguson N.M., Cummings D.A.T., Fraser C., Cajka J.C., Cooley P.C., and Burke D.S. Nature 442 (2006) 448
4. Kaye D., and Pringle C.R. Clin. Infect. Dis. 40 (2005) 108
5. Beigel J.H., Farrar J., Han A.M., Hayden F.G., Hyer R., De Jong M.D., Lochindarat S., Tien N.T.K., Hien N.T., Hien T.T., Nicoll A., Touch S., and Yuen K.Y. N. Engl. J. Med. 353 (2005) 1374
6. Hay A.J., Wolstenholme A.J., Skehel J.J., and Smith M.H. EMBO J. 4 (1985) 3021
7. Hay A.J. Semin. Virol. 3 (1992) 21
8. Pinto L.H., Holsinger L.J., and Lamb R.A. Cell 69 (1992) 517
9. In: Wolff M.E. (Ed). Burger's Medicinal Chemistry Part II (1998), John Wiley & Sons, New York 590-591
10. Kolocouris N., Foscolos G.B., Kolocouris A., Marakos P., Pouli N., Fytas G., Ikeda S., and De Clercq E. J. Med. Chem. 37 (1994) 2896
11. Kolocouris N., Kolocouris A., Foscolos G.B., Fytas G., Neyts J., Padalko E., Balzarini J., Snoeck R., Graciela A., and De Clercq E. J. Med. Chem. 39 (1996) 3307
12. Zoidis G., Kolocouris N., Foscolos G.B., Kolocouris A., Fytas G., Karayannis P., Padalko E., Neyts J., and De Clercq E. Antiviral Chem. Chemother. 14 (2003) 153
13. Zoidis G., Fytas C., Papanastasiou I., Foscolos G.B., Fytas G., Padalko E., De Clercq E., Naesens L., Neyts J., and Kolocouris N. Bioorg. Med. Chem. 14 (2006) 3341
14. De Clercq E. Nat. Rev. Drug Disc. 5 (2006) 1015
15. Duff K.C., Gilchrist P.J., Saxena A.M., and Bradshaw J.P. Virology 202 (1994) 287
16. Wang C., Takeuchi K., Pinto L.W., and Lamb R.A. J. Virol. 67 (1993) 5585
17. Chizhmakov I.V., Geragthy F.M., Ogden D.C., Hayhurst A., Antoniou M., and Hay A.J. J. Physiol. 494 (1996) 329
18. Ciampor F., Bayley P.M., Nermut M.V., Hirst E.M.A., Sugrue R.J., and Hay A.J. Virology 188 (1992) 14
19. Gandhi C.S., Shuck K., Lear J.D., Dieckmann G.R., DeGrado W.F., Lamb R.A., and Pinto L.H. J. Biol. Chem. 274 (1999) 5474
20. World Health Organization. Control of tropical diseases: sleeping sickness. WHO, 1994, Geneva, Switzerland.
21. Gompel A.V., and Vervoort T. Curr. Opin. Infect. Dis. 10 (1997) 469
22. Pepin J., and Milford F. Adv. Parasitol. 33 (1994) 1
23. Kelly J.M., Miles M.A., and Skinner A.C. Antimicrob. Agents Chemother. 43 (1999) 985
24. Kelly J.M., Quack G., and Miles M.A. Antimicrob. Agents Chemother. 45 (2001) 1360
25. Sasaki T., Eguchi S., and Hirako Y. Tetrahedron 32 (1976) 437
26. Borch R.F., and Hassid A.I. J. Org. Chem. 39 (1972) 1673
27. Birkofer L., and Schramm J. Liebigs Ann. Chem. (1975) 2195
28. Reiffers S., Strating J., and Wynberg H. Tetrahedron Lett. 12 (1971) 2339
29. Zoidis G., Papanastasiou I., Dotsikas I., Sandoval A., and Dos Santos R.G. Bioorg. Med. Chem. 13 (2005) 2791
30. 13C NMR spectra were assigned using COSY and CHCORR spectroscopy. The NMR spectra assignment of the spiro[azetidine-3,2′-adamantane] 13, spiro[piperidine-4,2′-adamantane] 25, and spiro barbituric analog 18 is given as Supplementary information.
31. Stamatiou G., Foscolos G.B., Fytas G., Kolocouris A., Kolocouris N., Pannecouque C., Witvrouw M., Padalko E., Neyts J., and De Clercq E. Bioorg. Med. Chem. 11 (2003) 5485
32. Pauwels R., Balzarini J., Baba M., Snoeck R., Schols D., Herdewijn P., Desmyter J., and De Clercq E. J. Virol. Methods 20 (1988) 309