Cross-coupling reactions as valuable tool for the preparation of PET radiotracers

Molecules

Volumn 16, Issue 2, 2011, Pages 1129-1165

  Pretze, Marc ^a   Große Gehling, Philipp ^b   Mamat, Constantin ^a  

^a INSTITUTE OF ION BEAM PHYSICS AND MATERIALS RESEARCH   (Germany)

^b DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Carbon 11; Cross coupling; Fluorine 18; Radiolabeling

Indexed keywords

CARBON; FLUORINE; RADIOPHARMACEUTICAL AGENT;

CHEMICAL STRUCTURE; CHEMISTRY; ISOTOPE LABELING; METHODOLOGY; POSITRON EMISSION TOMOGRAPHY; REVIEW;

CARBON RADIOISOTOPES; FLUORINE RADIOISOTOPES; ISOTOPE LABELING; MOLECULAR STRUCTURE; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS;

EID: 79952178716     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16021129     Document Type: Review

References (121)

1. Diederich, F.; Stang, P.J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, Germany, 2001.
2. Wu, X.-F.; Anbarasan, P.; Neumann, H. Beller, M. Vom Edelmetall zum Nobelpreis: Palladiumkatalysierte Kupplungen als Schlüsselmethode in der organischen Chemie. Angew. Chem. 2010, 122, 9231-9234.
3. Mamat, C.; Ramenda, T.; Wuest, F.R. Recent Applications of Click Chemistry for the Synthesis of Radiotracers for Molecular Imaging. Mini-Rev. Org. Chem. 2009, 6, 21-34.
4. Glaser, M.; Robins, E.G. 'Click labelling' in PET radiochemistry. J. Labelled Compd. Radiopharm. 2009, 52, 407-414.
5. Pfennig, G.; Klewe-Nebenius, H.; Seelmann-Eggebert, W. Karlsruher Nuklidkarte; Haberbeck: Lage, Germany, 2009.
6. Antoni, G.; Kihlberg, T.; Långström, B. Handbook of Radiopharmaceuticals, Radiochemistry and Applications; Welch, M.J.,Redvanly, C.S., Ed.; John Wiley & Sons: Chichester, UK, 2003; Chapter 5, pp. 141-195.
7. Scott, P.J.H. Methoden für den Einbau von Kohlenstoff-11 zur Erzeugung von Radiopharmaka für die Positronenemissionstomographie. Angew. Chem. 2009, 121, 6115-6118.
8. Allard, M.; Fouquet, E.; James, D.; Szlosek-Pinaud, M. State of the Art in 11C Labelled Radiotracers Synthesis. Curr. Med. Chem. 2008, 15, 235-277. (Pubitemid 351265134)
9. Oberdorfer, F.; Hanisch, M.; Helus, F.; Maier-Borst, W. A New Procedure for the Preparation of 11C-Labelled Methyl Iodide. Int. J. Appl. Radiat. Isot. 1985, 36, 435-438. (Pubitemid 15065526)
10. Holschbach, M.; Schüller, M. A New and Simple On-line Method for the Preparation of n.c.a. [11C]Methyl Iodide. Appl. Radiat. Isot. 1993, 44, 779-780. (Pubitemid 23089951)
11. Larsen, P.; Ulin, J.; Dahlstrom, K.; Jensen, M. Synthesis of [11C]Iodomethane by of [11C]Methane Iodination. Appl. Radiat. Isot. 1997, 48, 153-157.
12. Buckley, K.R.; Jivan, S.; Ruth, T.J. Improved yields for the in situ production of [11C]CH4 using a niobium target chamber. Nucl. Med. Biol. 2004, 31, 825-827. (Pubitemid 38887767)
13. Zhang, M.-R.; Suzuki, K. Sources of carbon which decrease the specific activity of [11C]CH3I synthesized by the single pass I2 method. Appl. Radiat. Isot. 2005, 62, 447-450. (Pubitemid 39655925)
14. Matarrese, M.; Soloviev, D.; Todde, S.; Neutro, F.; Petta, P.; Carpinelli, A.; Brüssermann, M.; Kienle, M.G.; Fazio, F. Preparation of [11C] radioligands with high specific radioactivity on a commercial PET tracer synthesizer. Nucl. Med. Biol. 2003, 30, 79-83. (Pubitemid 35454165)
15. Stille, J.K.; Palladium-katalysierte Kupplungsreaktionen organischer Elektrophile mit Organozinn- Verbindungen. Angew. Chem. 1986, 98, 504-519.
16. Mitchell, T.N. Palladium-Catalysed Reactions of Organotin Compounds. Synthesis 1992, 803-815.
17. Andersson, Yvonne; Cheng, Aiping; Långström, Bengt, Palladium-promoted Coupling Reactions of [11C]Methyl Iodide with Organotin and Organoboron Compounds. Acta. Chem. Scand. 1995, 49, 683-688.
18. Suzuki, M.; Doi, H.; Björkman, M.; Andersson, Y.; Långström, B.; Watanabe, Y.; Noyori, R. Rapid Coupling of Methyl Iodide with Aryltributylstannanes Mediated by Palladium(0) Complexes: A General Protocol for the Synthesis of 11CH3-Labeled PET Tracers. Chem. Eur. J. 1997, 3, 2039-2042. (Pubitemid 28028907)
19. Björkman, M.; Doi, H.; Resul, B.; Suzuki, M.; Noyori, R.; Watanabe, Y.; Långström, B. F2a Analogue Using An Improved Method For Stille Reactions With [11C]Methyl Iodide. J. Labelled Compd. Radiopharm. 2000, 43, 1327-1334.
20. Sandell, J.; Halldin, C.; Sovago, J.; Chou, Y.-H.; Gulyás, B.; Yu, M.; Emond, P.; Någren, K.; Guilloteau, D.; Farde, L. PET examination of [11C]5-methyl-6-nitroquipazine, a radioligand for visualization of the serotonin transporter. Nucl. Med. Biol. 2002, 29, 651-656. (Pubitemid 35266664)
21. Langer, O.; Forngren, T.; Sandell, J.; Dollé, F.; Långström, B.; Någren, K.; Halldin, C. Preparation of 4-[11C]methylmetaraminol, a potential PET tracer for assessment of myocardial sympathetic innervation. J. Labelled Compd. Radiopharm. 2003, 46, 55-65. (Pubitemid 36125624)
22. Forngren, T.; Samuelsson, L.; Långström, B. A 11C-Methyl stannane (5-[11C]methyl-1-aza-5- stannabicyclo[3.3.3]undecane) for use in palladium-mediated [11C]C-C bond forming reactions with organohalides. J. Labelled Compd. Radiopharm. 2004, 47, 71-78. (Pubitemid 38166414)
23. Reiffers, S.; Vaalburg, W.; Wiegman, T.; Wynberg, H.; Woldring, M.G. Carbon-11 labelled methyllithium as methyl donating agent: The addition to 17-Keto steroids. Int. J. Appl. Radiat. Isot. 1980, 31, 535-539. (Pubitemid 10027275)
24. Karimi, F.; Barletta, J.; Långström, B. Palladium-Mediated 11C-Carbonylative Cross-Coupling of Alkyl/Aryl Iodides with Organostannanes: An Efficient Synthesis of Unsymmetrical Alkyl/Aryl [11C-carbonyl]Ketones. Eur. J. Org. Chem. 2005, 2374-2378. (Pubitemid 40830744)
25. Arai, T.; Kato, K.; Zhang, M.R. Synthesis of [carbonyl-11C]acetophenone via the Stille crosscoupling reaction of [1-11C]acetyl chloride with tributylphenylstannane mediated by Pd2(dba)3/P(MeNCH2CH2)3N•HCl. Tetrahedron Lett. 2009, 50, 4788-4791.
26. Liu, X.; Verkade, J.G. Free and Polymer-Bound Tricyclic Azaphosphatranes HP(RNCH2CH2)3N+: Procatalysts in Dehydrohalogenations and Debrominations with NaH. J. Org. Chem. 1999, 64, 4840-4843.
27. Huiban, M.; Huet, A.; Barré, L.; Sobrio, F.; Fouquet, E.; Perrio, C. Methyl transfer reaction from monomethyltin reagent under palladium(0) catalysis: A versatile method for labelling with carbon- 11. Chem. Commun. 2006, 97-99.
28. Harris, D.H.; Lappert, M.F.J. Monomeric, volatile bivalent amides of group IVB elements, M(NR1 2)2 and M(NR1R2)2(M=Ge, Sn, or Pb; R1=Me3Si, R2=Me3C) J. Chem. Soc. Chem. Commun. 1974, 895-896.
29. Giardina, G.A.M.; Sarau, H.M.; Farina, C.; Medhurst, A.D.; Grugni, M.; Foley, J.J.; Raveglia, L.F.; Schmidt, D.B.; Rigolio, R.; Vassallo, M.; Vecchietti, V.; Hay, D.W.P. 2-Phenyl-4- quinolinecarboxamides: A Novel Class of Potent and Selective Non-Peptide Competitive Antagonists for the Human Neurokinin-3 Receptor. J. Med. Chem. 1996, 39, 2281-2284. (Pubitemid 26187381)
30. Bourdier, T.; Huiban, M.; Huet, A.; Sobrio, F.; Fouquet, E.; Perrio, C.; Barré, L. Tetra- and Monoorganotin Reagents in Palladium-Mediated Cross-Coupling Reactions for the Labeling with Carbon-11 of PET Tracers. Synthesis 2008, 978-984. (Pubitemid 351450250)
31. Langer, O.; Forngren, T.; Sandell, J.; Dollé, F.; Långström, B.; Någren, K.; Halldin, C. Preparation of 4-[11C]methylmetaraminol, a potential PET tracer for assessment of myocardial sympathetic innervation. J. Labelled Compd. Radiopharm. 2003, 46, 55-65. (Pubitemid 36125624)
32. Samuelsson, L.; Långström, B. Synthesis of 1-(2'-deoxy-2'-fluoro-β-d-arabinofuranosyl)-[Methyl- 11C]thymine ([11C]FMAU) via a Stille cross-coupling reaction with [11C]methyl iodide. J. Labelled Compd. Radiopharm. 2003, 46, 263-272. (Pubitemid 36373159)
33. Toyohara, J.; Okada, M.; Toramatsu, C.; Suzuki, K.; Irie, T. Feasibility studies of 4'-[methyl- 11C]thiothymidine as a tumor proliferation imaging agent in mice. Nucl. Med. Biol. 2008, 35, 67-74. (Pubitemid 350298251)
34. Kawamura, K.; Shi, K.; Tsukada, H.; Nishiyama, S.; Mori, H.; Ishiwata, K. Synthesis and evaluation of vesamicol analog (-)-o-[11C]methylvesamicol as a PET ligand for vesicular acetylcholine transporter. Ann. Nucl. Med. 2006, 20, 417-424. (Pubitemid 44259807)
35. Toyohara, J.; Sakata, M.; Wu, J.; Ishikawa, M.; Oda, K.; Ishii, K.; Iyo, M.; Hashimoto, K.; Ishiwata, K. Preclinical and the first clinical studies on [11C]CHIBA-1001 for mapping a7 nicotinic receptors by positron emission tomography. Ann. Nucl. Med. 2009, 23, 301-309.
36. Lu, S.; Hong, J.; Itoh, T.; Fujita, M.; Inoue, O.; Innis, R.B.; Pike, V.W. [carbonyl-11C]Benzyl acetate: Automated radiosynthesis via Pd-mediated [11C]carbon monoxide chemistry and PET measurement of brain uptake in monkey. J. Labelled Compd. Radiopharm. 2010, 53, 548-551.
37. Hosoya, T.; Sumi, K.; Doi, H.; Wakao, M.; Suzuki, M. Rapid methylation on carbon frameworks useful for the synthesis of 11CH3-incorporated PET tracers: Pd(0)-mediated rapid coupling of methyl iodide with an alkenyltributylstannane leading to a 1-methylalkene. Org. Biomol. Chem. 2006, 4, 410-415.
38. Kawamura, K.; Naganawa, M.; Konno, F.; Yui, J.; Wakizaka, H.; Yamasaki, T.; Yanamoto, K.; Hatori, A.; Takei, M.; Yoshida, Y.; Sakaguchi, K.; Fukumura, T.; Kimura, Y.; Zhang, M.-R. Imaging of I2-imidazoline receptors by small-animal PET using 2-(3-fluoro-[4-11C]tolyl)-4,5- dihydro-1H-imidazole ([11C]FTIMD). Nucl. Med. Biol. 2010, 37, 625-635.
39. Bennacef, I.; Perrio, C.; Lasne, M.-C.; Barré, L. Functionalization through Lithiation of (S)-N-(1- Phenylpropyl)-2- phenylquinoline-4-carboxamide. Application to the Labeling with Carbon-11 of NK-3 Receptor Antagonist SB 222200. J. Org. Chem. 2007, 72, 2161-2165. (Pubitemid 46418422)
40. Madsen, J.; Merachtsaki, P.; Davoodpour, P.; Bergström, M.; Långström, B.; Andersen, K.; Thomsen, C.; Martiny, L.; Knudsen, G. M. Synthesis and Biological Evaluation of Novel Carbon- 11-Labelled Analogues of Citalopram as Potential Radioligands for the Serotonin Transporter. Bioorg. Med. Chem. 2003, 11, 3447-3456. (Pubitemid 36870985)
41. Tarkiainen, J.; Vercouillie, J.; Emond, P.; Sandell, J.; Hiltunen, J.; Frangin, Y.; Guilloteau, D.; Halldin, C. Carbon-11 labelling of MADAM in two different positions: A highly selective PET radioligand for the serotonin transporter. J. Labelled Compd. Radiopharm. 2001, 44, 1013-1023.
42. Yu, M.; Tueckmantel, W.; Wang, X.; Zhu, A.; Kozikowski, A.P.; Brownell, A.-L. Methoxyphenylethynyl, methoxypyridylethynyl and phenylethynyl derivatives of pyridine: Synthesis, radiolabeling and evaluation of new PET ligands for metabotropic glutamate subtype 5 receptors. Nucl. Med. Biol. 2005, 32, 631-640. (Pubitemid 40981819)
43. Hamill, T.G.; Krause, S.; Ryan, C.; Bonnefous, C.; Govek, S.; Seiders, T.J.; Cosford, N.D.P.; Roppe, J.; Kamenecka, T.; Patel, S.; Gibson, R.E.; Sanabria, S.; Riffel, K.; Eng, W.; King, C.; Yang, X.; Green, M.D.; O'Malley, S.S.; Hargreaves, R.; Burns, H.D. Synthesis, Characterization, and First Successful Monkey Imaging Studies of Metabotropic Glutamate Receptor Subtype 5 (mGluR5) PET Radiotracers. Synapse 2005, 56, 205-216. (Pubitemid 40656643)
44. Huang, Y.; Narendran, R.; Bischoff, F.; Guo, N.; Zhu, Z.; Bae, S.; Lesage, A.S.; Laruelle, M. A Positron Emission Tomography Radioligand for the in Vivo Labeling of Metabotropic Glutamate 1 Receptor: (3-Ethyl-2-[11C]methyl-6- quinolinyl)(cis-4-methoxycyclohexyl)methanone. J. Med. Chem. 2005, 48, 5096-5099. (Pubitemid 41113895)
45. Björkman, M.; Andersson, Y.; Doi, H.; Kato, K.; Suzuki, M.; Noyori, R.; Watanabe, Y.; Långström, B. Synthesis of 11C/13C-Labelled Prostacyclins. Acta Chem. Scand. 1998, 52, 635-640.
46. Suzuki, M.; Doi, H.; Kato, K.; Björkman, M.; Långström, B.; Watanabe, Y.; Noyori, R. Rapid Methylation for the Synthesis of a 11C-Labeled Tolylisocarbacyclin Imaging the IP2 Receptor in a Living Human Brain. Tetrahedron 2000, 56, 8263-8273.
47. Suzuki, M.; Doi, H.; Hosoya, T.; Långström, B.; Watanabe, Y. Rapid methylation on carbon frameworks leading to the synthesis of a PET tracer capable of imaging a novel CNS-type prostacyclin receptor in living human brain. Trends Anal. Chem. 2004, 23, 595-607. (Pubitemid 39232082)
48. Prabhakaran, J.; Majo, V.J.; Simpson, N.R.; Van Heertum, R.L.; Mann, J.J.; Kumar, J.S.D. Synthesis of [11C]celecoxib: A potential PET probe for imaging COX-2 expression. J. Labelled Compd. Radiopharm. 2005, 48, 887-895. (Pubitemid 41659193)
49. Karimi, F.; Långström, B. Synthesis of 3-[(2S)-azetidin-2- ylmethoxy]-5-[11C]-methylpyridine, an analogue of A-85380, via a Stille coupling. J. Labelled Compd. Radiopharm. 2002, 45, 423-434. (Pubitemid 34464648)
50. Iida, Y.; Ogawa, M.; Ueda, M.; Tominaga, A.; Kawashima, H.; Magata, Y.; Nishiyama, S.; Tsukada, H.; Mukai, T.; Saji, H. Evaluation of 5-11C-Methyl-A-85380 as an Imaging Agent for PET Investigations of Brain Nicotinic Acetylcholine Receptors. J. Nucl. Med. 2004, 45, 878-884. (Pubitemid 47618569)
51. Suzuki A. Synthetic studies via the cross-coupling reaction of organoboron derivatives with organic halides. Pure and Appl. Chem. 1991, 63, 419-422.
52. Ishiyama T.; Kizaki H.; Miyaura N.; Suzuki A. Synthesis of unsymmetrical biaryl ketones via palladiumcatalyzed cross-coupling reaction of aryboronic acids with iodoarenes. Tetrahedron Lett. 1993, 34, 7595-7598.
53. Miyaura N.; Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483.
54. Zeisler, S.K.; Nader, M.; Theobald, A.; Oberdorfer, F. Conversion of No-carrier-added [11C]carbon dioxide to [11C]carbon monoxide on molybdenum for the synthesis of 11C-labelled aromatic ketones, Appl. Radiat. Isot. 1997, 48, 1091-1095. (Pubitemid 27483699)
55. Nader, M.W.; Oberdorfer, F. Syntheses of [carbonyl-11C]2-(2- benzoylphenoxy)-N-phenylacetamide from [11C]carbon monoxide by the Suzuki and the Stille reactions. Appl. Radiat. Isot. 2002, 57, 681-685. (Pubitemid 35279157)
56. Rahman, O.; Llop, J.; Långström, B. Organic Bases as Additives to Improve the Radiochemical Yields of [11C]Ketones Prepared by the Suzuki Coupling Reaction. Eur. J. Org. Chem. 2004, 2674-2678.
57. Colquhoun, H.M.; Thompson, D.J.; Twigg, M.V. Carbonylation; Plenum Press: New York, NY, USA, 1991.
58. Rahman, O.; Kihlberg, T.; Långström, B. Synthesis of 11C-/13C-Ketones by Suzuki Coupling. Eur. J. Org. Chem. 2004, 474-478.
59. Hostetler, E.D.; Terry, G.E.; Burns, H.D. An improved synthesis of substituted [11C]toluenes via Suzuki coupling with [11C]methyl iodide. J. Labelled Compd. Radiopharm. 2005, 48, 629-634. (Pubitemid 41206316)
60. De Meijere, A.; Meyer, F.E. Kleider machen Leute: Heck-Reaktion im neuen Gewand. Angew. Chem. 1994, 106, 2473-2506.
61. Björkman, M.; Långström, B. Functionalisation of 11C-labelled olefins via a Heck coupling reaction. J. Chem. Soc. Perkin Trans. 1 2000, 3031-3034. (Pubitemid 35290639)
62. Chinchilla, R.; Nájera, C. The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry. Chem. Rev. 2007, 107, 874-922. (Pubitemid 46504819)
63. Wuest, F.; Zessin, J.; Johannsen, B. A new approach for 11C-C bond formation: Synthesis of 17a- (3'-[11C]prop-1-yn-1-yl)-3-methoxy-3,17β- estradiol. J. Labelled Compd. Radiopharm. 2003, 46, 333-342. (Pubitemid 36514055)
64. Wuest, F.; Berndt, M. 11C-C bond formation by palladium-mediated cross-coupling of alkenylzirconocenes with [11C]methyl iodide. J. Labelled Compd. Radiopharm. 2006, 49, 91-100. (Pubitemid 43384885)
65. Hart, D.W.; Schwartz, J. Hydrozirconation. Organic Synthesis via organozirconium intermediates. Synthesis and rearrangement of alkylzirconium(IV) complexes and their reaction with electrophiles. J. Am. Chem. Soc. 1974, 96, 8115-8116.
66. Tarkiainen, J.; Vercouillie, J.; Emond, P.; Sandell, J.; Hiltunen, J.; Frangin, Y.; Guilloteau, D.; Halldin, C. Carbon-11 labelling of MADAM in two different positions: A highly selective PET radioligand for the serotonin transporter. J. Label. Compd. Radiopharm. 2001, 44, 1013-1023.
67. Lasne, M.C.; Pike, V.W.; Turton, D,R. The radiosynthesis of [-methyl-11C]-sertraline. Int. J. Radiat. Appl. Instrum., Part A 1989, 40, 147-151.
68. Eriksson, J.; Åberg, O.; Långström, B. Synthesis of [11C]/[13C]Acrylamides by Palladium-Mediated Carbonylation. Eur. J. Org. Chem. 2007, 455-461.
69. Amatore, C.; Jutand, A. Role of dba in the reactivity of palladium(0) complexes generated in situ from mixtures of Pd(dba)2 and phosphines. Coord. Chem. Rev. 1998, 178-180, 511-528. (Pubitemid 128451207)
70. Andersson, Y.; Långström, B. Transition Metal-mediated Reactions using [11C]Cyanide in Synthesis of 11C-labelled Aromatic Compounds. J. Chem. Soc. Perkin Trans. 1 1994, 1395-1400.
71. Sandell, J.; Halldin, C.; Hall, H.; Thorberg, S.-O.; Werner, T.; Sohn, D.; Sedvall, G.; Farde, L. Radiosynthesis and Autoradiographic Evaluation of [11C]NAD-299, a Radioligand for Visualization of the 5-HT1A Receptor. Nucl. Med. Biol. 1999, 26, 159-164. (Pubitemid 29125332)
72. Bennacef, I.; Salinas, C.A.; Bonasera, T.A.; Gunn, R.N.; Audrain, H.; Jakobsen, S.; Nabulsi, N.; Weinzimmer, D.; Carson, R.E.; Huang, Y.; Holmes, I.; Micheli, F.; Heidbreder, C.; Gentile, G.; Rossi, T.; Laruelle, M. Dopamine D3 receptor antagonists: The quest for a potentially selective PET ligand. Part 3: Radiosynthesis and in vivo studies. Bioorg. Med. Chem. Lett. 2009, 19, 5056-5059.
73. Lidström, P.; Neu, H.; Långström, B. Syntheses of [21-11C] and (21-13C) progesterone. J. Labelled Compd. Radiopharm. 1997, 40, 695-704.
74. J. Labelled Compd. Radiopharm. 1997, 40, 783-784.
75. Madsen, J.; Merachtsaki, P.; Davoodpour, P.; Bergström, M.; Långström, B.; Andersen, K.; Thomsen, C.; Martiny, L.; Knudsen, G.M. Synthesis and Biological Evaluation of Novel Carbon- 11-Labelled Analogues of Citalopram as Potential Radioligands for the Serotonin Transporter. Bioorg. Med. Chem. 2003, 11, 3447-3456. (Pubitemid 36870985)
76. Tucker, C.E.; Knochel, P. Cross-Coupling between Functionalized Alkylcopper Reagents and Functionalized Alkyl Halides. J. Org. Chem. 1993, 58, 4781-4782.
77. Wuest, F.; Dence, C.S.; McCarthy, T.J.; Welch, M.J. A New Approach for the Synthesis of [11C]- Labeled Fatty Acids. J. Labelled Compd. Radiopharm. 2000, 43, 1289-1300.
78. Cenini, S.; Pizzotti, M.; Porta, F.; La Monica, G. Isocyanate, urea and amide complexes from the reactions of organic azides with low oxidation state complexes of transition metals. J. Organomet. Chem. 1975, 88, 237-248.
79. Doi, H.; Barletta, J.; Suzuki, M.; Noyori, R.; Watanabe, Y.; Långström, B. Synthesis of 11Clabelled N,N'-diphenylurea and ethyl phenylcarbamate by a rhodium-promoted carbonylation via [11C]isocyanatobenzene using phenyl azide and [11C]carbon monoxide. Org. Biomol. Chem. 2004, 2, 3063-3066.
80. Ilovich, O.; Åberg, O.; Långström, B.; Mishania, E. Rhodium-mediated [11C]Carbonylation: A library of N-phenyl-N'-{4-(4-quinolyloxy) -phenyl}-[11C]-urea derivatives as potential PET angiogenic probes. J. Labelled Compd. Radiopharm. 2008, 52, 151-157.
81. La Monica, G.; Ardizzoia, G. Five-membered Heterocycles by the Rh(I)-Catalysed Carbonylation of Aromatic ortho-Substituted Azides. J. Mol. Catal. 1986, 38, 327-330. (Pubitemid 17497424)
82. Vallabhajosula, S. Molecular Imaging, Springer: Berlin, Heidelberg, Germany, 2008, pp. 151-164.
83. Miller, P.W.; Long, N.J.; Vilar, R.; Gee, A.D. Synthese von 11C-, 18F-, 15O- und 13N-Radiotracern für die Positronenemissionstomographie. Angew. Chem. 2008, 120, 9136-9172.
84. Kima, D.W.; Choeb, Y.S.; Chi, D.Y. A new nucleophilic fluorine-18 labeling method for aliphatic mesylates: Reaction in ionic liquids shows tolerance for water. Nucl. Med. Biol. 2003, 30, 345-350. (Pubitemid 36589041)
85. Le Bars, D. Fluorine-18 and medical imaging: Radiopharmaceuticals for positron emission tomography. J. Fluorine Chem. 2006, 127, 1488-1493.
86. Wuest, F.; Berndt, M.; Kniess, T. Recent Advances of Bioconjugation Chemistry in Molecular Imaging; Chen, X., Ed.; Research Signpost: Kerala, India, 2008; pp. 155-173.
87. Piarraud, A.; Lasne, M.C.; Barré, L.; Vaugeois, J.M.; Lancelot, J.C. Synthesis of no carrier added [18f] Gbr 12936 via a wittig reaction for use in a the dopamine reuptake site study. J. Labelled Compd. Radiopharm. 1993, 32, 253-254.
88. Hantraye, P.; Brownell, A.-L.; Elmaleh, D.; Spealman, R.D.; Wüllner, U.; Brownell, G.L.; Madras, B.K.; Isacson, O. Dopamine fiber detection by [11C]-CFT and PET in a primate model of parkinsonism. Neuroreport 1992, 3, 265-268.
89. Allain-Barbier, L.; Lasne, M.C.; Huard C.; Barré, L. Palladium Mediated Synthesis of [18F]Fluorophenyl Alkenes or Arenes. J. Labelled Compd. Radiopharm. 1995, 37, 572-574.
90. Allain-Barbier, L.; Lasne, M.C.; Perrio-Huard C.; Moreau, B.; Barré, L. Synthesis of [18F]Fluorophenyl Alkenes or Arenes via Palladium-Catalyzed Coupling of 4-[18F]Fluoroiodobenzene with Vinyl and Aryl Tin Reagents. Acta Chem. Scand. 1998, 52, 480-489. (Pubitemid 128549784)
91. Gail, R.; Coenen, H.H. A one step preparation of the n.c.a. Fluorine-18 labelled synthons: 4- Fluorobromobenzene and 4-fluoroiodobenzene. Appl. Radiat. Isot. 1994, 45, 105-111.
92. Forngren, T.; Andersson, Y.; Lamm, B.; Långström, B. Palladium-Mediated Coupling Reactions of 18F-Labelled Arylhalides with Organotin Compounds. J. Labelled Compd. Radiopharm. 1995, 37, 595-596.
93. Plenevaux, A.; Lemaire, C.; Palmer, A.J.; Damhaut, P.; Comar, D. Synthesis of non-activated 18Ffluorinated aromatic compounds through nucleophilic substitution and decarboxylation reactions. Int. J. Radiat. Appl. Instrument. Part A; Appl. Radiat. Isot. 1992, 43, 1035-1040.
94. Forngren, T.; Andersson, Y.; Lamm, B.; Långström, B. Synthesis of [4-18F]-1-Bromo-4- fluorobenzene and its Use in Palladium-Promoted Cross-Coupling Reactions with Organostannanes. Acta Chem. Scand. 1998, 52, 475-479. (Pubitemid 128549783)
95. Marrière, E.; Rouden, J.; Tadino, V.; Lasne, M.C. Synthesis of Analogues of (-)-Cytisine for in Vivo Studies of Nicotinic Receptors Using Positron Emission Tomography. Org. Lett. 2000, 2, 1121-1124.
96. Holladay, M.W.; Dart, M.J.; Lynch, J.K. Neuronal Nicotinic Acetylcholine Receptors as Targets for Drug Discovery, J. Med. Chem. 1997, 40, 4169-4194. (Pubitemid 28042300)
97. Wüst, F.R.; Kniess, T. Synthesis of 4-[18F]fluoroiodobenzene and its application in sonogashira cross-coupling reactions. J. Labelled Compd. Radiopharm. 2003, 46, 699-713. (Pubitemid 36890059)
98. Mangner, T.J.; Klecker, R.W.; Anderson, L.; Shields, A.F. Synthesis of 2'-deoxy-2'-[18F]fluoro-β- D-arabinofuranosyl nucleosides, [18F]FAU, [18F]FMAU, [18F]FBAU and [18F]FIAU, as potential PET agents for imaging cellular proliferation: Synthesis of [18F]labelled FAU, FMAU, FBAU, FIAU. Nucl. Med. Biol. 2003, 30, 215-224.
99. Toyohara, J.; Fujibayashi, Y. Trends in nucleoside tracers for PET imaging of cell proliferation. Nucl. Med. Biol. 2003, 30, 681-685. (Pubitemid 37123124)
100. Brust, P.; Haubner, R.; Friedrich, A.; Scheunemann, M.; Anton, M.; Koufaki, O.-N.; Hauses, M.; Noll, S.; Noll, B.; Haberkorn, U.; Schackert, G.; Schackert, H.K.; Avril, N.; Johannsen, B. Comparison of [18F]FHPG and [124/125I]FIAU for imaging herpes simplex virus type 1 thymidine kinase gene expression. Eur. J. Nucl. Med. Mol. Imaging 2001, 28, 721-729
101. Wüst, F.R.; Kniess, T. No-carrier added synthesis of 18F-labelled nucleosides using Stille crosscoupling reactions with 4-[18F]fluoroiodobenzene. J. Labelled Compd. Radiopharm. 2004, 47, 457-468. (Pubitemid 39062537)
102. Marnett, L.J. Cyclooxygenase mechanisms. Curr. Opin. Chem. Biol. 2000, 4, 545-552.
103. Wüst, F.R.; Höhne, A.; Metz, P. Synthesis of 18F-labelled cyclooxygenase-2 (COX-2) inhibitors via Stille reaction with 4-[18F]fluoroiodobenzene as radiotracers for positron emission tomography (PET). Org. Biomol. Chem. 2005, 3, 503-507. (Pubitemid 40285717)
104. Li, J.J.; Anderson, G.D.; Burton, E.G.; Cogburn, J.N.; Collins, J.T.; Garland, J.D.; Gregory, S.A.; Huang, H.; Isakson, P.C.; Koboldt, C.M.; Logusch, E.W.; Norton, M.B.; Perkins, W.E.; Reinhard, E.J.; Seibert, K.; Veenhuizen, A.W.; Zhang, Y.; Reitz, D.B. 1,2-Diarylcyclopentenes as Selective Cyclooxygenase-2 Inhibitors and Orally Active Anti-inflammatory Agents. J. Med. Chem. 1995, 38, 4570-4578.
105. Steininger, B.; Wuest, F.R. Synthesis of 18F-labelled biphenyls via SUZUKI cross-coupling with 4-[18F]fluoroiodobenzene. J. Labelled Compd. Radiopharm. 2006, 49, 817-827. (Pubitemid 44367557)
106. Marrière, E.; Chazalviel, L.; Dhilly, M.; Toutain, J.; Perrio, C.; Dauphin, F.; Lasne, M.C. Synthesis of [18F]RP 62203, a potent and selective Serotonin 5-HT2A Receptor Antagonist and Biological Evaluation with ex vivo Autoradiography. J. Labelled Compd. Radiopharm. 1999, 42, S69-S71. (Pubitemid 29371204)
107. Malleron, J.L.; Comte, M.T.; Gueremy, C.; Peyronel, J.F.; Truchon, A.; Blanchard, J.C.; Doble, A.; Piot, O.; Zundel, J.L. Naphthosultam Derivatives: A New Class of Potent and Selective 5-HT2 Antagonists, J. Med. Chem. 1991, 34, 2477-2483.
108. Das, M.K.; Mukherjee, J.; [18F]RP 62203: A High Affinity and Selective Radioligand as a Potential PET Tracer for Serotonin 5HT2 Receptor; J. Labelled Compd. Radiopharm. 1994, 35, 497-499. (Pubitemid 24159437)
109. Collins, M.; Lasne, M.-C.; Barré, L. Rapid synthesis of N,N'-disubstituted piperazines. Application to the preparation of No carrier added 1-(4-[18F]fluorophenyl)piperazine and of an [18F]-selective ligand of serotoninergic receptors (5HT2 antagonist). J. Chem. Soc. Perkin Trans. 1 1992, 23, 3185-3188.
110. Lasne, M.C.; Le Secq, B.; Barre, L.; Collins, M.; Huard, C.; Baron, J.C. Synthesis of [18F]RP 62203, a Selective Antagonist of 5HT2 Receptors for Positron Emission Tomography Studies. J. Labelled Compd. Radiopharm. 1994, 35, 441-443. (Pubitemid 24159413)
111. Stabler, S. R.; Jahangir. Preparation of N-Arylated Heterocycles by Nucleophilic Aromatic Substitution. Synth. Commun. 1994, 24, 123-129. (Pubitemid 24125219)
112. Mor, M.; Plazzi, P.V.; Rivara S. 2-[N-Acylamino(C1-C3)alkyl]indoles as MT1 Melatonin Receptor Partial Agonists, Antagonists, and Putative Inverse Agonists. J. Med. Chem. 1998, 41, 3624-3634. (Pubitemid 28449344)
113. Andersen, K.; Liljefors, T.; Hyttel, J.; Perregaard, J. Serotonin 5-HT2 Receptor, Dopamine D2 Receptor, and a1 Adrenoceptor Antagonists. Conformationally Flexible Analogues of the Atypical Antipsychotic Sertindole. J. Med. Chem. 1996, 39, 3723-3738. (Pubitemid 26307878)
114. Perregaard, J.; Moltzen, E.K.; Meier, E.; Sanchez, C. s Ligands with Subnanomolar Affinity and Preference for the s2 Binding Site. 1. 3-(β-Aminoalkyl)-1H-indoles. J. Med. Chem. 1995, 38, 1998-2008.
115. Sánchez, C.; Arnt, J.; Costall, B.; Kelly, M.E.; Meier, E.; Naylor, R.J.; Perregaard, J. The Selective s2-Ligand Lu 28-179 Has Potent Anxiolytic-Like Effects in Rodents. J. Pharmacol. Exp. Ther. 1997, 283, 1333-1341.
116. Wüst, F.R.; Kniess, T. N-Arylation of indoles with 4-[18F]fluoroiodobenzene: Synthesis of 18Flabelled s2 receptor ligands for positron emission tomography (PET). J. Labelled Compd. Radiopharm. 2005, 48, 31-43.
117. Lee, B.-C.; Dence, C.S.; Zhou, H.; Parent, E.E.; Welch, M.J.; Katzenellenbogen, J.A. Fluorine-18 labeling and biodistribution studies on peroxisome proliferator-activated receptor-? ligands: Potential positron emission tomography imaging agents. Nucl. Med. Biol. 2009, 36, 147-153.
118. Henke, B.R.; Blanchard, S.G.; Brackeen, M.F.; Brown, K.K.; Cobb, J.E.; Collins, J.L.; Harrington, W.W., Jr.; Hashim, M.A.; Hull-Ryde, E.A.; Kaldor, I.; Kliewer, S.A.; Lake, D.H.; Leesnitzer, L.M.; Lehmann, J.M.; Lenhard, J.M.; Orband-Miller, L.A.; Miller, J.F.; Mook, R.A., Jr.; Noble, S.A.; Oliver, W., Jr.; Parks, D.J.; Plunket, K.D:; Szewczyk, J.R:; Willson, T.M. N-(2- Benzoylphenyl)-l-tyrosine PPARγ agonists: 1. Discovery of a Novel Series of Potent Antihyperglycemic and Antihyperlipidemic Agents. J. Med. Chem. 1998, 41, 5020-5036. (Pubitemid 28555461)
119. Young, P.W.; Buckle, D.R.; Cantello, B.C.C.; Chapman, H.; Clapham, J.C.; Coyle, P.J.; Haigh, D.; Hindley, R.M.; Holder, J.C.; Kallender, H.; Latter, A.J.; Lawrie, K.W.M.; Mossakowska, D.; Murphy, G.J.; Cox, L.R.; Smith, S.A. Identification of High-Affinity Binding Sites for the Insulin Sensitizer Rosiglitazone (BRL-49653) in Rodent and Human Adipocytes Using a Radioiodinated Ligand for Peroxisomal Proliferator-Activated Receptor γ. J. Pharmacol. Exp. Ther. 1998, 284, 751-759. (Pubitemid 28086668)
120. Pretze, M.; Flemming, A.; Köckerling, M.; Mamat, C. Synthesis and Radiofluorination of Iodophenyl Esters as Tool for the Traceless Staudinger Ligation. Z. Naturforsch. 2010, 65b, 1128-1136.
121. Pretze, M.; Wuest, F.; Peppel, T.; Köckerling, M.; Mamat, C. The traceless Staudinger ligation with fluorine-18: A novel and versatile labeling technique for the synthesis of PET-radiotracers. Tetrahedron Lett. 2010, 51, 6410-6414.