Tetra- and Monoorganotin Reagents in Palladium-Mediated Cross-Coupling Reactions for the Labeling with Carbon-11 of PET Tracers

Abstract

The palladium-catalyzed cross-coupling reactions between a (trimethylstannyl)arene and [¹¹C]methyl iodide (Stille reaction) or between an aryl halide and a [¹¹C]monomethyltin reagent issued from Lappert’s stannylene, were developed for the synthesis of polyfunctional [¹¹C]methyl quinolines and quinolinimides as potential tracers for positron emission tomography (PET).

Key words

positron emission tomography - carbon-11 - Stille - monoorganotin­ - [¹¹C]methyl iodide

References

• 1 Fowler JS. Wolf AP. Barrio JR. Mazziotta JC. Phelps ME. In Positron Emission Tomography and Autoradiography   Phelps ME. Mazziotta JC. Schelbert HR. Raven Press; New York: 1986.  Chap. 9-11.
• 2 Långström B. Dannals RF. In Principles of Nuclear Medicine   Wagner HN. Szabo Z. Buchanan JW. W. B. Saunders W. B.; Philadelphia PA: 1995. 
• 3a Fowler JS. Wolf AP. Acc. Chem. Res.  1997,  30:  181 
• 3b Ouari O. Polidori A. Pucci B. Tordo P. Chalier F. J. Org. Chem.  1999,  64:  3554 
• 4 Crouzel C. Långström B. Pike VW. Coenen HH. Appl. Radiat. Isot.  1987,  38:  601 
• 5 Buckman BO. VanBrocklin HF. Dence CS. Bergmann SR. Welch MJ. Katzenellenbogen JA. J. Med. Chem.  1994,  37:  2481 
• 6 Khilberg T. Långström B. Acta Chem. Scand.  1994,  48:  570 
• 7 Wüst F. Dence CS. McCarthy TJ. Welch MJ. J. Labelled Compd. Radiopharm.  2000,  43:  1289 
• 8 Hostetler ED. Fallis S. McCarthy TJ. Welch MJ. Katzenellenbogen JA. J. Org. Chem.  1998,  63:  1348 
• 9 Andersson Y. Cheng A. Långström B. Acta Chem. Scand.  1995,  49:  683 
• 10 Suzuki M. Doi H. Björkman M. Andersson Y. Långström B. Watanabe Y. Noyori R. Chem. Eur. J.  1997,  3:  2039 
• 11 Björkman M. Andersson Y. Doi H. Kato K. Suzuki M. Noyori R. Watanabe Y. Långström B. Acta Chem. Scand.  1998,  52:  635 
• 12 Björkman M. Doi H. Resul B. Suzuki M. Noyori R. Watanabe Y. Långström B. J. Labelled Compd. Radiopharm.  2000,  43:  1327 
• 13 Suzuki M. Doi H. Björkman M. Långström B. Watanabe Y. Noyori R. Tetrahedron  2000,  56:  8263 
• 14 Tarkiainen J. Vercouillie J. Emond P. Sandell J. Hiltunen J. Frangin Y. Guilloteau D. Halldin C. J. Labelled Compd. Radiopharm.  2001,  44:  1013 
• 15 Sandell J. Yu M. Emond P. Garreau L. Chalon S. Någren K. Guilloteau D. Halldin C. Bioorg. Med. Chem. Lett.  2002,  12:  3611 
• 16 Karimi F. Långström B. J. Labelled Compd. Radiopharm.  2002,  45:  423 
• 17 Madsen J. Merachtsaki P. Davoodpour P. Bergström M. Långström B. Andersen K. Thomsen C. Martiny L. Knudsen GM. Bioorg. Med. Chem.  2003,  11:  3447 
• 18 Langer O. Forngren T. Sandell J. Dollé F. Långström B. Någren K. Halldin C. J. Labelled Compd. Radiopharm.  2003,  46:  55 
• 19 Samuelsson L. Långström B. J. Labelled Compd. Radiopharm.  2003,  46:  263 
• 20 Antoni G. Khilberg T. Långström B. In Handbook of Radiopharmaceuticals, Radiochemistry and Applications   Welch MJ. Redvanly CS. Wiley; Chichester: 2003.  p.141-194  
• 21 Huiban M. Huet A. Barré L. Sobrio F. Fouquet E. Perrio C. Chem. Commun.  2006,  97 
• 22 Harris DH. Lappert MF. J. Chem. Soc., Chem. Commun.  1974,  895 
• 23 Schaeffer CD. Zuckerman JJ. J. Am. Chem. Soc.  1974,  96:  7160 
• 24 Giardina GAM. Sarau HM. Farina C. Medhurst AD. Grugni M. Foley JJ. Raveglia LF. Schmidt DB. Rigolio R. Vassallo M. Vecchietti V. Hay DWP. J. Med. Chem.  1996,  39:  2281 
• 25 Giardina GAM. Raveglia LF. Grugni M. Sarau HM. Farina C. Medhurst AD. Graziani D. Schmidt DB. Rigolio R. Luttmann M. Cavagnera S. Foley JJ. Vecchietti V. Hay DWP. J. Med. Chem.  1999,  42:  1053 
• 26 Sarau HM. Griswold DE. Potts B. Bush W. Sandhu P. Lundberg D. Foley JJ. Schmidt DB. Webb EF. Martin LD. Legos JJ. Whitmore RG. Barone FC. Medhurst AD. Luttmann MA. Giardina GAM. Hay DWP. J. Pharmacol. Exp. Ther.  2000,  295:  373 
• 27 Langlois X. Te Riele P. Wintmolders C. Leysen JE. Jurzak M. J. Pharmacol. Exp. Ther.  2001,  299:  712 
• 28 Bennacef I. Perrio C. Lasne M.-C. Barré L. J. Org. Chem.  2007,  72:  2161 
• 29 Quinolines 3 and 4 were original compounds synthesized in our laboratory. Their affinities towards NK-3 receptors were identical to that of SB 222200. For in vitro evaluation experimental procedure, see: Bennacef I. Tymciu S. Dhilly M. Mongin F. Quéguiner G. Lasne M.-C. Barré L. Perrio C. J. Org. Chem.  2004,  69:  2622 
• 30 Barn DR. Caulfield WL. Cottney J. McGurk K. Morphy JR. Rankovic Z. Roberts B. Bioorg. Med. Chem.  2001,  9:  2609 
• 31 Bourdier T. Poisnel G. Dhilly M. Delamare J. Henry J. Debruyne D. Barré L. Bioconjugate Chem.  2007,  18:  538 
• 32 Hervé A. Rodriguez AL. Fouquet E. J. Org. Chem.  2005,  70:  1953 
• 33 Bennacef I. Tymciu S. Dhilly M. Lasne M.-C. Debruyne D. Perrio C. Barré L. Bioorg. Med. Chem.  2004,  12:  4533