Efficient synthesis of [ 11C]H-1152, a PET probe specific for Rho-kinases, highly potential targets in diagnostic medicine and drug development

Tetrahedron

Volumn 68, Issue 10, 2012, Pages 2336-2341

  Suzuki, Masaaki ^a   Takashima Hirano, Misato ^a   Koyama, Hiroko ^b   Yamaoka, Takafumi ^b   Sumi, Kengo ^b   Nagata, Hiroko ^a   Hidaka, Hiroyoshi ^c   Doi, Hisashi ^a  

^a RIKEN   (Japan)

^b GIFU UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^c Western Therapeutics Inc   (Japan)

Author keywords

C C Coupling; HMPA; Lithiation; Positron emission tomography (PET); Rho kinase H 1152

Indexed keywords

AMINE; DIAGNOSTIC AGENT; H 1152; H 1152 C 11; HEMPA; ISOQUINOLINE; RADIOPHARMACEUTICAL AGENT; RHO KINASE; RHO KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DEPROTECTION REACTION; DRUG SYNTHESIS; DRUG TARGETING; ISOTOPE LABELING; LITHIATION; METHYLATION; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RADIOACTIVITY; RADIOCHEMISTRY; RADIODIAGNOSIS; STANNYLATION;

EID: 84862801890     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.01.033     Document Type: Article

References (43)

1. M. Suzuki, H. Doi, M. Björkman, Y. Andersson, B. Lngström, Y. Watanabe, and R. Noyori Chem. - Eur. J. 3 1997 2039 2042
2. M. Suzuki, R. Noyori, B. Lngström, and Y. Watanabe Bull. Chem. Soc. Jpn. 73 2000 1053 1070
3. M. Suzuki, H. Doi, K. Kato, M. Björkman, B. Lngström, Y. Watanabe, and R. Noyori Tetrahedron 56 2000 8263 8273
4. M. Björkman, H. Doi, B. Resul, M. Suzuki, R. Noyori, Y. Watanabe, and B. Lngström J. Labelled Compd. Radiopharm. 43 2000 1327 1334
5. T. Hosoya, M. Wakao, Y. Kondo, H. Doi, and M. Suzuki Org. Biomol. Chem. 2 2004 24 27
6. M. Suzuki, H. Doi, T. Hosoya, B. Lngström, and Y. Watanabe Trends Anal. Chem. 23 2004 595 607
7. T. Hosoya, K. Sumi, H. Doi, M. Wakao, and M. Suzuki Org. Biomol. Chem. 4 2006 410 415
8. Patent: Suzuki, M.; Hosoya, T. JP 2005-306670, WO2007/046258
9. Patent: Suzuki, M.; Doi, H.; Tsukada, H. JP 2006-229169, WO2008/023780
10. H. Doi, I. Ban, A. Nonoyama, K. Sumi, C. Kuang, T. Hosoya, H. Tsukada, and M. Suzuki Chem. - Eur. J. 15 2009 4165 4171
11. M. Suzuki, K. Sumi, H. Koyama, Siqin, M. Hosoya, M. Takashima-Hirano, and H. Doi Chem. - Eur. J. 15 2009 12489 12495
12. Patent: Suzuki, M.; Doi, H.; Koyama, H. JP 2008-335250, WO2010/074272
13. M. Kanazawa, K. Furuta, H. Doi, T. Mori, T. Minami, S. Ito, and M. Suzuki Bioorg. Med. Chem. Lett. 21 2011 2017 2020
14. H. Koyama, Siqin, Z. Zhang, K. Sumi, Y. Hatta, H. Nagata, H. Doi, and M. Suzuki Org. Biomol. Chem. 9 2011 4287 4294 for further application to molecular imaging, see
15. T. Takashima, H. Nagata, T. Nakae, Y. Cui, Y. Wada, S. Kitamura, H. Doi, M. Suzuki, K. Maeda, H. Kusuhara, S. Sugiyama, and Y. Watanabe J. Pharmacol. Exp. Ther. 335 2010 314 323
16. Takashima, T.; Kitamura, S.; Wada, Y.; Tanaka, M.; Shigihara, Y.; Ishii, H.; Ijuin, R.; Shiomi, S.; Nakae, T.; Watanabe, Y.; Cui, Y.; Doi, H.; Suzuki, M.; Maeda, K.; Kusuhara, H.; Sugiyama, Y.; Watanabe, Y. J. Nucl. Med., in press.
17. K. Rient, and A.J. Ridley Nat. Mol. Cell Biol. 4 2003 446 456
18. M. Ikenoya, H. Hidaka, T. Hosoya, M. Suzuki, N. Yamamoto, and Y. Sasaki J. Neurochem. 81 2002 9 16
19. K. Noma, N. Oyama, and J.K. Liao Am. J. Physiol., Cell Physiol. 290 2006 C661 C668
20. N. Wettshureck, and S. Offermanns J. Mol. Med. 80 2002 629 638
21. B.K. Mueller, H. Mack, and N. Teusch Nat. Rev. Drug Discovery 4 2005 387 398
22. K. Kimura, M. Ito, M. Amano, K. Chihara, Y. Fukata, M. Nakafuku, B. Tamamori, J. Feng, T. Nakano, K. Okawa, A. Iwamatsu, and K. Kakibuchi Science (Washington, D.C.) 273 1996 245 248
23. T. Asano, I. Ikegaki, S. Satoh, Y. Suzuki, M. Shibuya, M. Takayasu, and H. Hidaka J. Pharmacol. Exp. Ther. 241 1987 1033 1040
24. Y. Feng, Y. Yin, A. Weiser, E. Griffin, M.D. Cameron, L. Lin, C. Ruix, S.C. Schürer, T. Inoue, P.V. Rao, T. Schröter, and P. LoGrasso J. Med. Chem. 51 2008 6642 6645 and references cited therein
25. Hidaka, H.; Matsuura, A.; Matsuzaki, T. WO9728130, Aug. 7, 1997
26. Y. Sasaki, M. Ikenoya, N. Yamamoto, M. Suzuki, and H. Hidaka Cell. Mol. Biol. Lett. 6 2001 506
27. Y. Sasaki, M. Suzuki, and H. Hidaka Pharmacol. Ther. 93 2002 225 232 see also Ref. 3
28. M.E. Phelps PET: Molecular Imaging and Its Biological Applications 2004 Springer New York, NY
29. J.S. Fowler, and A.P. Wolf Acc. Chem. Res. 30 1997 181 188
30. S.M. Ametamey Chem. Rev. 108 2008 1501 1516
31. P.W. Miller, N.J. Long, R. Vilar, and A.D. Gee Angew. Chem., Int. Ed. 47 2008 8998 9033
32. The extremely low polarity of the tributyltin(IV) derivative enables easy separation of the desired product from a large excess of the remaining tin substrate. In addition, it should be noted that tributyl derivative is practically non-toxic, while trimethyl- and triethyltins have a significant acute toxicity. For the toxicity of tin, see: P.J. Smith P.J. Smith, Chemistry of TIN 2nd ed. 1998 Blackie Academic & Professional London, UK 429 441
33. B. Buck, A. Mascioni, L. Que Jr. , and G. Veglia J. Am. Chem. Soc. 125 2003 13316 13317
34. A. Nagaki, H. Kim, and J. Yoshida Angew. Chem., Int. Ed. 47 2008 7833 7836 and references cited therein
35. D.W. Slocum, D. Kusmic, J.C. Raber, T.K. Reinscheld, and R.E. Whitley Tetrahedron Lett. 51 2010 4793 4796
36. C. Nájera, J.M. Sansano, and M. Yus Tetrahedron 59 2003 9255 9303
37. M. Suzuki, H. Koyama, and R. Noyori Tetrahedron 60 2004 1571 1579
38. M. Suzuki, H. Koyama, and R. Noyori Bull. Chem. Soc. Jpn. 77 2004 259 268
39. H.J. Reich, D.P. Green, M.A. Medina, W.S. Goldenberg, B.Ö. Gudmundsson, R.R. Dykstra, and N.H. Phillips J. Am. Chem. Soc. 120 1998 7201 7210
40. W.H. Sikorski, and H.J. Reich J. Am. Chem. Soc. 123 2001 6527 6535 see also
41. R. Noyori, I. Nishida, and J. Sakata J. Am. Chem. Soc. 105 1983 1598 1608
42. i=0.15 μM, much lesser affinity than that of 3). However, to the best of our knowledge, any inhibitory effect of N-methyl-hydroxyfasudil for Rho-kinase and its selectivity for other serine/threonine protein kinases have not been reported; see: A.C. Valdivia, S. Mason, J. Collins, K.R. Buckley, P. Colett, R.S. Beanlands, and J.N. DaSilva Appl. Radiat. Isot. 68 2010 325 328
43. Hidaka, H.; Masahiro, N.; Sumi, K. U.S. Patent 20081164681, March 13, 2008.