Synthesis of novel deuterium labelled derivatives of N-alkylated polyamines

Tetrahedron

Volumn 65, Issue 2, 2009, Pages 547-562

  Häkkinen, Merja R ^a   Keinänen, Tuomo A ^b   Khomutov, Alex R ^c   Auriola, Seppo ^b   Weisell, Janne ^a   Alhonen, Leena ^b   Jänne, Juhani ^b   Vepsäläinen, Jouko ^a  

^a Department of Biosciences   (Finland)

^b UNIVERSITY OF EASTERN FINLAND   (Finland)

^c ENGELHARDT INSTITUTE OF MOLECULAR BIOLOGY   (Russian Federation)

Author keywords

Deuterated; Deuterated polyamines; N Alkylated polyamine analogues; Polyamines

Indexed keywords

DEUTERIUM; POLYAMINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

TETRA;

EID: 56949103507     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.071     Document Type: Article

References (54)

1. Jänne J., Alhonen L., Keinänen T.A., Pietilä M., Uimari A., Pirinen E., Hyvönen M.T., and Järvinen A. J. Cell. Mol. Med. 9 (2005) 865-882
2. Wallace H.M., Fracer A.V., and Hughes A. Biochem. J. 376 (2003) 1-14
3. Gugliucci A. Clin. Chim. Acta 344 (2004) 23-35
4. Karigiannis G., and Papaioannou D. Eur. J. Org. Chem. (2000) 1841-1863
5. Casero Jr. R.A., and Marton L.J. Nat. Rev. Drug Discov. 6 (2007) 373-389
6. Casero Jr. R.A., and Woster P.M. J. Med. Chem. 44 (2001) 1-26
7. Boncher T., Bi X., Varghese S., Casero Jr. R.A., and Woster P.M. Biochem. Soc. Trans. 35 (2007) 356-363
8. Wallace H.M., and Niiranen K. Amino Acids 33 (2007) 261-265
9. Seiler N. Pharmacol. Ther. 107 (2005) 99-119
10. Bergeron R.J., Wiegand J., Weimar W.R., and Snyder P.S. Pharmacol. Res. 38 (1998) 367-380
11. Prakash C., Shaffer C.L., and Nedderman A. Mass Spectrom. Rev. 26 (2007) 340-369
12. Kostiainen R., Kotiaho T., Kuuranne T., and Auriola S. J. Mass Spectrom. 38 (2003) 357-372
13. Hakkinen M.R., Keinänen T.A., Vepsäläinen J., Khomutov A.R., Alhonen L., Jänne J., and Auriola A. J. Pharm. Biomed. Anal. 45 (2007) 625-634
14. Hakkinen M.R., Keinänen T.A., Vepsäläinen J., Khomutov A.R., Alhonen L., Jänne J., and Auriola A. J. Pharm. Biomed. Anal. 48 (2008) 414-421
15. Stokvis E., Rosing H., and Beijnen J.H. Rapid Commun. Mass Spectrom. 19 (2005) 401-407
16. Cleland W.W. Arch. Biochem. Biophys. 433 (2005) 2-12
17. Lee K.Y., Na J.E., Lee M.J., and Kim J.N. Tetrahedron Lett. 45 (2004) 5977-5981
18. Kuksa V., Buchan R., and Kong Thoo Lin P. Synthesis (2000) 1189-1207
19. Gawandi V., and Fitzpatric P.F. J. Labelled Compd. Radiopharm. 50 (2007) 666-670
20. Maruyoshi K., Demura T., Sagane T., Matsumori N., Oishi T., and Murata M. Tetrahedron 60 (2004) 5163-5170
21. Smith R.G., and Daves Jr. G.D. Biomed. Mass Spectrom. 4 (1977) 146-151
22. Jentgens C., Bienz S., and Hesse M. Helv. Chim. Acta 80 (1997) 1133-1143
23. Schere G., and Limbach H.-H. J. Am. Chem. Soc. 116 (1994) 1230-1239
24. Van Den Berg G.A., Elzinga H., Nagel G.T., Kingma A.W., and Muskiet F.A. J. Biochim. Biophys. Acta 802 (1984) 175-187
25. Fodor-Csorba K., Galli G., Holly S., and Gács-Baitz E. Tetrahedron Lett. 43 (2002) 3789-3792
26. Moser M., Hudlicky T., Sadechi S., and Sternin E. J. Labelled Compd. Radiopharm. 50 (2007) 671-674
27. Concellón J.M., Rodríguez-Solla H., and Concellón C. Tetrahedron Lett. 45 (2004) 2129-2131
28. Whitmore F.C., Mosher H.S., Adams R.R., Taylor R.B., Chapin E.C., Weisel C., and Yanko W. J. Am. Chem. Soc. 66 (1944) 725-731
29. Richard J.P., Williams G., and Gao J. J. Am. Chem. Soc. 121 (1999) 715-726
30. Iwasaki M., Sakka T., Ohashi S., and Matsushita H. J. Phys. Chem. 93 (1989) 5139-5143
31. Hidai Y., Kan T., and Fukuyama T. Chem. Pharm. Bull. 48 (2000) 1570-1576
32. Järvinen A.J., Cerrade-Gimenez M., Grigorenko N.A., Khomutov A.R., Vepsäläinen J.J., Sinervirta R.M., Keinänen T.A., Alhonen L.I., and Jänne J.E. J. Med. Chem. 49 (2006) 399-406
33. Grigorenko N.A., Khomutov A.R., Keinänen T.A., Järvinen A., Alhonen L., Jänne J., and Vepsäläinen J. Tetrahedron 63 (2007) 2257-2262
34. Pretsch E., Bühlmann P., and Affolter C. Structure Determination of Organic Compounds: Tables of Spectral Data. 3rd Completely revised and enlarged Engl. ed. (2000), Springer, Berlin p 247
35. Rouvier E., Pastor R., Musso J., and Cambon A. Org. Magn. Reson. 6 (1974) 640-643
36. Zhang H., Zhang Y., Liu L., Xu H., and Wang Y. Synthesis 13 (2005) 2129-2136
37. Pearson D.E., Jones W.H., and Cope A.C. J. Am. Chem. Soc. 68 (1946) 1225-1229
38. Dawber J.G., and Massey-Shaw J. J. Chem. Soc., Perkin Trans. 2 (1989) 1249-1254
39. Compounds 1a, 1h and 1j as free base:. Tarbell D.S., Shakespeare N., Claus C.J., and Bunnett J.F. J. Am. Chem. Soc. 68 (1946) 1217-1219
40. King J.A., and McMillan F.H. J. Am. Chem. Soc. 68 (1946) 1468-1470
41. Martin B., Possémé F., Le Barbier C., Carreaux F., Carboni B., Seiler N., Moulinoux J.-P., and Delcros J.-G. J. Med. Chem. 44 (2001) 3653-3664
42. Bolkenius F.N., and Seiler N. Biol. Chem. Hoppe-Seyler 370 (1989) 525-531
43. Compound 1e as free base:. Surrey A. J. Am. Chem. Soc. 71 (1949) 3354-3356
44. Wysocka-Skrzela B., Cholody W.M., and Ledochowski A. Pol. J. Chem. 55 (1981) 2211-2214
45. Wagner-Jauregg T. Helv. Chim. Acta 44 (1961) 1237-1249
46. Callery P.S., Subramayam B., Yuan Z.-M., Pou S., Geelhaar L.A., and Reynolds K.A. Chem.-Biol. Interact. 85 (1992) 15-26
47. Bergeron R.J., Feng Y., Weimar W.R., McManis J.S., Dimova H., Porter C., Raisler B., and Phanstiel O. J. Med. Chem. 40 (1997) 1475-1494
48. Carboni B., Benalil A., and Vaultier M. J. Org. Chem. 58 (1993) 3736-3741
49. da Silva E.T., Fona F.S., and Lima E.L.S. J. Braz. Chem. Soc. 15 (2004) 433-436
50. Olsen C.A., Jorgensen M.R., Witt M., Mellor I.R., Usherwood P.N.R., Jaroszewski J.W., and Franzyk H. Eur. J. Org. Chem. (2003) 3288-3299
51. Bergeron R.J., McManis J.S., Liu C.Z., Feng Y., Weimar W.R., Luchetta G.R., Wu Q., Ortiz-Ocasio J., Vinson J.R.T., Kramer D., and Porter C. J. Med. Chem. 37 (1994) 3464-3476
52. Tomasi S., Le Roch M., Renault J., Corbel J.-C., Uriac P., Carboni B., Moncoq D., Martin B., and Delcros J.-G. Bioorg. Med. Chem. Lett. 8 (1998) 635-640
53. Bergeron R.J., Wiegand J., McManis J.S., Weimar W.R., Smith R.E., Algee S.E., Fannin T.L., Slusher M.A., and Snyder P.S. J. Med. Chem. 44 (2001) 232-244
54. Weitl F.L., and Raymond K.N. J. Org. Chem. 46 (1981) 5234-5237