Synthesis and pharmacological evaluation of several ring-contracted amantadine analogs

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 23, 2008, Pages 9925-9936

  Camps, Pelayo ^a   Duque, María D ^a   Vázquez, Santiago ^a   Naesens, Lieve ^b   Clercq, Erik De ^b   Sureda, Francesc X ^c   López Querol, Marta ^c   Camins, Antoni ^a   Pallàs, Mercè ^a   Prathalingam, S Radhika ^d   Kelly, John M ^d   Romero, Vanessa ^e   Ivorra, Dolores ^e   Cortés, Diego ^e  

^a UNIVERSITY OF BARCELONA   (Spain)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^c FACULTAT DE MEDICINA I CIÈNCIES DE LA SALUT   (Spain)

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

^e UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Amantadine; Influenza; Memantine; NMDA receptor antagonist; Polycyclic cage compounds; Trypanosomiasis

Indexed keywords

1 [3,7 DIMETHYLTRICYCLO(3.3.0.0 3,7)OCT 1 YL]ETHYLAMINE HYDROCHLORIDE; 3,7 DIMETHYL[TRICYCLO(3.3.0.0 3,7)OCY 1 YL]AMINE HYDROCHLORIDE; AMANTADINE; ANTITRYPANOSOMAL AGENT; ANTIVIRUS AGENT; DOPAMINE UPTAKE INHIBITOR; MEMANTINE; N (2 METHOXYBENZYL)(TRICYCLO[3.3.1.0 3,7]NON 3 YL)AMINE HYDROCHLORIDE; N (2 THENYL) 3,7 DIMETHYL[TRICYCLO(3.3.0.0 3,7)OCY 1 YL]AMINE HYDROCHLORIDE; N (2 THENYL)(TRICYCLO[3.3.1.0 3,7]NON 3 YL)AMINE HYDROCHLORIDE; N (3 METHOXYBENZYL)(TRICYCLO[3.3.1.0 3,7]NON 3 YL)AMINE HYDROCHLORIDE; N (4 FLUOROBENZYL)(TRICYCLO[3.3.1.0 3,7]NON 3 YL)AMINE HYDROCHLORIDE; N (4 METHOXYBENZYL)(TRICYCLO[3.3.1.0 3,7]NON 3 YL)AMINE HYDROCHLORIDE; N (TRICYCLO[3.3.1.0 3,7]NON 3 YL)PIPERIDINE HYDROCHLORIDE; N BENZYL 3,7 DIMETHYL[TRICYCLO(3.3.0.0 3,7)OCY 1 YL]AMINE HYDROCHLORIDE; N BENZYL N METHYL(TRICYCLO[3.3.1.0 3,7]NON 3 YL)AMINE HYDROCHLORIDE; N BENZYL N METHYL[[TRICYCLO(3.3.1.0 3,7)NON 3 YL]METHYL]AMINE HYDROCHLORIDE; N BENZYL(TRICYCLO[3.3.1.0 3,7]NON 3 YL)AMINE HYDROCHLORIDE; N BENZYL[[3,7 DIMETHYLTRICYCLO(3.3.0.0 3,7)OCT 1 YL]METHYL]AMINE HYDROCHLORIDE; N BENZYL[[TRICYCLO(3.3.1.0 3,7)NON 3 YL]METHYL]AMINE HYDROCHLORIDE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; N METHYL(TRICYCLO[3.3.1.0 3,7]NON 3 YL)AMINE HYDROCHLORIDE; N METHYL[[TRICYCLO(3.3.1.0 3,7)NON 3 YL]METHYL]AMINE HYDROCHLORIDE; N [[TRICYCLO(3.3.1.0 3,7)NON 3 YL]METHYL]GUANIDINE HYDROCHLORIDE; N,N 3,7 TETRAMETHYL[TRICYCLO(3.3.0.0 3,7)OCT 1 YL]AMINE HYDROCHLORIDE; N,N DIMETHYL[[TRICYCLO(3.3.1.0 3,7)NON 3 YL]METHYL]AMINE HYDROCHLORIDE; RIMANTADINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; [[3,7 DIMETHYLTRICYCLO(3.3.0.0 3,7)OCT 1 YL]METHYL]AMINE HYDROCHLORIDE; [[TRICYCLO(3.3.1.0 3,7)NON 3 YL]METHYL]AMINE HYDROCHLORIDE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIPROTOZOAL ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CYTOPATHOGENIC EFFECT; DOPAMINE UPTAKE; DRUG SYNTHESIS; FEMALE; INFLUENZA VIRUS A; INHIBITION KINETICS; NONHUMAN; RAT; TRYPANOSOMA BRUCEI; TRYPANOSOMIASIS; WISTAR RAT;

INFLUENZA A VIRUS;

EID: 55749115608     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.10.028     Document Type: Article

References (56)

1. Aoki F. Textbook of Influenza. In: Nicholson K.G., Webster R.G., and Hay A.J. (Eds) (1998), Blackwell Science, Oxford 457-476
2. De Clercq E. Nat. Rev. Drug Discovery 5 (2006) 1015
3. Geluk H.W., Schut J., and Schlatmann J.L.M.A. J. Med. Chem. 12 (1969) 712
4. Aldrich P.E., Hermann E.C., Meier W.E., Paulshock M., Prichard W.W., Snyder J.A., and Watts J.C. J. Med. Chem. 14 (1971) 535
5. Tilley T.W., Levitan P., and Kramer M.J. J. Med. Chem. 22 (1979) 1009
6. 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
7. Kolocouris N., Kolocouris A., Foscolos G.B., Fytas G., Neyts J., Padalko E., Balzarini J., Snoeck R., Andrei G., and De Clercq E. J. Med. Chem. 39 (1996) 3307
8. Van Derpoorten K., Balzarini J., De Clercq E., and Poupaert J.H. Biomed. Pharmacother. 51 (1997) 464
9. Scholtissek C., Quack G., Klenk H.D., and Webster R.G. Antiviral Res. 37 (1998) 83
10. Burstein M.E., Serbin A.V., Khakhulina T.V., Alymova I.V., Stotskaya L.L., Bogdan O.P., Manukchina E.E., Jdanov V.V., and Sharova N.K. Antiviral Res. 41 (1999) 135
11. Stylianakis I., Kolocouris A., Kolocouris N., Fytas G., Foscolos G.B., Padalko E., Neyts J., and De Clercq E. Bioorg. Med. Chem. Lett. 13 (2003) 1699
12. El-Emam A.A., Al-Deeb O.A., Al-Omar M., and Lehmann J. Bioorg. Med. Chem. 12 (2004) 5107
13. Danysz W., Parsons C.G., Kornhuber J., Schmidt W.J., and Quack G. Neurosci. Biobehav. Rev. 21 (1997) 455
14. Palmer G.C. Curr. Drug Targets 2 (2001) 241
15. Kelly J.M., Miles M.A., and Skinner A.C. Antimicrob. Agents Chemother. 43 (1999) 985
16. Kelly J.M., Quack G., and Miles M.A. Antimicrob. Agents Chemother. 45 (2001) 1360
17. Martínez A.G., Vilar E.T., Fraile A.G., Cerezo S.D., Herrero M.E.R., Ruiz P.M., Subramanian L.R., and Gancedo A.G. J. Med. Chem. 38 (1995) 4474
18. Miller J.A., Ullah G.M., Welsh G.M., and Hall A.C. Tetrahedron Lett. 42 (2001) 7503
19. Gregory, W. A. U.S. Patent 3 558 704, 1971.
20. Aigami K., Inamoto Y., Takaishi N., Fujikura Y., Takatsuki A., and Tamura G. J. Med. Chem. 19 (1976) 536
21. Zhou J.J.P., Li J., Upadhyaya S., Eaton P.E., and Silverman R.B. J. Med. Chem. 40 (1997) 1165
22. Geldenhuys W.J., Malan S.F., Bloomquist J.R., Marchand A.P., and van der Schyf C.J. Med. Res. Rev. 25 (2005) 21
23. Geldenhuys W.J., Malan S.F., Bloomquist J.R., and van der Schyf C.J. Bioorg. Med. Chem. 15 (2007) 1525
24. Camps P., and Muñoz-Torrero D. Tetrahedron Lett. 35 (1994) 3187
25. Camps P., Font-Bardia M., Muñoz-Torrero D., and Solans X. Liebigs Ann. (1995) 523
26. Camps P., Muñoz-Torrero D., and Muñoz-Torrero V. Tetrahedron Lett. 36 (1995) 1917
27. Camps P., and Figueredo M. Can. J. Chem. 62 (1984) 1184
28. Camps P., Iglesias C., Rodríguez M.J., Grancha M.D., Gregori M.E., Lozano R., Miranda M.A., Figueredo M., and Linares A. Chem. Ber. 121 (1988) 647
29. Camps P., Estiarte M.A., Vázquez S., and Pérez F. Synth. Commun. 25 (1995) 1287
30. Camps P., Font-Bardia M., Pérez F., Solans X., and Vázquez S. Angew. Chem., Int. Ed. Engl. 34 (1995) 912
31. Camps P., Luque F.J., Orozco M., Pérez F., and Vázquez S. Tetrahedron Lett. 37 (1996) 8605
32. Camps P., Lukach A., and Vázquez S. Tetrahedron 57 (2001) 2419
33. Camps P., Lukach A., Pujol X., and Rossi R.A. J. Org. Chem. 66 (2001) 5366
34. Camps P., Pujol X., and Vázquez S. Tetrahedron 58 (2002) 10081
35. Ayats C., Camps P., Duque M.D., Font-Bardia M., Muñoz M.R., Solans X., and Vázquez S. J. Org. Chem. 68 (2003) 8715
36. Camps P., Muñoz M.R., and Vázquez S. J. Org. Chem. 70 (2005) 1945
37. Camps P., Fernández J.A., Font-Bardia M., Solans X., and Vázquez S. Tetrahedron 61 (2005) 3593
38. Ayats C., Camps P., Font-Bardia M., Muñoz M.R., Solans X., and Vázquez S. Tetrahedron 62 (2006) 7436
39. Camps P., Muñoz M.R., and Vázquez S. Tetrahedron 62 (2006) 7645
40. Ayats C., Camps P., Fernández J.A., and Vázquez S. Chem. Eur. J. 13 (2007) 1522
41. Camps P., Colet G., Delgado S., Muñoz M.R., Pericàs M.A., Solà Ll., and Vázquez S. Tetrahedron 63 (2007) 4669
42. Ayats C., Camps P., Font-Bardia M., Solans X., and Vázquez S. Tetrahedron 63 (2007) 8027
43. We found a patent that claimed antiviral activity for some bisnor- and nor-adamantane derivatives, but activity details are not given. See, Hoover, J. R. E. U.S. Patent 3496228, 1970. For the anti-influenza activity of 7 see Ref. 2g.
44. Patrick G.L. An Introduction to Medicinal Chemistry (2005), Oxford University Press, Oxford pp 204-205
45. Jawdosiuk M., and Kovacic P. Synth. Commun. 13 (1983) 53
46. Casanova J., and Devi P. Synth. Commun. 23 (1993) 245
47. Okazaki T., Isobe H., Kitagawa T., and Takeuchi K. Bull. Chem. Soc. Jpn. 69 (1996) 2053
48. Barret M.P. Lancet 367 (2006) 1377
49. Kolocouris N., Zoidis G., Foscolos G.B., Fytas G., Prathalingam R., Kelly J.M., Naesens L., and De Clercq E. Bioorg. Med. Chem. Lett. 17 (2007) 4358
50. Papanastasiou I., Tsotinis A., Kolocouris N., Prathalingam R., and Kelly J.M. J. Med. Chem. 51 (2008) 1496
51. Robinson D.M., and Keating G.M. Drugs 66 (2006) 1515
52. Canudas A.M., Pubill D., Sureda F.X., Verdaguer E., Camps P., Muñoz-Torrero D., Jiménez A., Camins A., and Pallàs M. Exp. Neurol. 180 (2003) 123
53. Mizoguchi K., Yokoo H., Yoshida M., Tanaka T., and Tanaka M. Brain Res. 662 (1994) 255
54. Hirumi H., and Hirumi K. J. Parasitol. 75 (1989) 985
55. De Clercq E., Cools M., Balzarini J., Márquez V.E., Borcherding D.R., Borchardt R.T., Drach J.C., Kitaoka S., and Konno T. Antimicrob. Agents Chemother. 33 (1989) 1291
56. Setaki D., Tataridis D., Stamatiou G., Kolocouris A., Foscolos G.B., Fytas G., Kolocouris N., Padalko E., Neyts J., and De Clercq E. Bioorg. Chem. 34 (2006) 248