Добавил:
kiopkiopkiop18@yandex.ru t.me/Prokururor I Вовсе не секретарь, но почту проверяю Опубликованный материал нарушает ваши авторские права? Сообщите нам.
Вуз: Предмет: Файл:
Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_5903_Библиотеки_им_академика_М_И_Перельмана.pdf
Скачиваний:
0
Добавлен:
15.09.2026
Размер:
17 Мб
Скачать
☆
6. Zimmer, L. and Le Bars, D. (2013). Current status of positron emission tomography radiotracers for serotonin receptors in humans. J. Labelled Compd. Radiopharm. 56 (3–4): 105–113. https://doi.org/10.1002/jlcr.3001.
7. Kovac, M., Mavel, S., and Anderluh, M. (2013). direct introduction of [
18
F]uoride into electron-rich arenes. Curr. Org. Chem. 17 (15):
18
F-Labeled aryl-tracers through
2921–2935.
8. Cole, E.L., Stewart, M.N., Littich, R. etal. (2014). Radiosyntheses using uorine-18: the art and science of late stage uorination. Curr. Top. Med. Chem. 14 (7): 875–900. https://doi.org/10.2174/1568026614666140202205035.
9. Brooks, A.F., Topczewski, J.J., Ichiishi, N. etal. (2014). Late-stage [
18
F]uorination: new solutions to old problems. Chem. Sci. 5 (12): 4545–4553. https://doi.org/10.1039/ C4SC02099E.
10. Brooks, A.F., Drake, L.R., Stewart, M.N. etal. (2016). Fluorine-18 patents (2009–2015). Part 1: novel radiotracers. Pharm. Pat. Anal. 5 (1): 17–47. https://doi.org/10.4155/ppa.15.36.
11. Mossine, A.V., Thompson, S., Brooks, A.F. etal. (2016). Fluorine-18 patents (2009–2015). Part 2: new radiochemistry. Pharm. Pat. Anal. 5 (5): 319–349. https://doi. org/10.4155/ppa-2016-0028.
12. Littich, R. and Scott, P.J.H. (2012). Novel strategies for uorine-18 radiochemistry. Angew. Chem. Int. Ed. 51 (5): 1106–1109. https://doi.org/10.1002/anie.201106785.
13. Campbell, M.G. and Ritter, T. (2015). Modern carbon–uorine bond forming reactions for aryl uoride synthesis. Chem. Rev. 115 (2): 612–633. https://doi.org/10.1021/cr500366b.
14. Liang, S.H. and Vasdev, N. (2015). Total radiosynthesis: thinking outside “the box.”. Aust. J. Chem. 68 (9): 1319. https://doi.org/10.1071/CH15406.
15. Edwards, R. and Wirth, T. (2015). [
18
F]6-uoro-3,4-dihydroxy-l-phenylalanine - recent modern syntheses for an elusive radiotracer. J. Labelled Compd. Radiopharm. 58 (5): 183–187. https://doi.org/10.1002/jlcr.3285.
16. Jacobson, O., Kiesewetter, D.O., and Chen, X. (2015). Fluorine-18 radiochemistry, labeling strategies and synthetic routes. Bioconjugate Chem. 26 (1): 1–18. https://doi. org/10.1021/acs.chemrev.5b00493.
17. Preshlock, S., Tredwell, M., and Gouverneur, V. (2016).
18
F-labeling of arenes and heteroarenes for applications in positron emission tomography. Chem. Rev. 116 (2): 719–766. https://doi.org/10.1021/acs.chemrev.5b00493.
18. Deng, X., Rong, J., Wang, L. etal. (2019). Chemistry for positron emission tomog­raphy: recent advances in
11
C-, 18F-, 13N-, and 15O-labeling reactions. Angew. Chem. Int.
Ed. 58 (9): 2580–2605. https://doi.org/10.1002/anie.201805501.
19. Coenen, H.H. and Ermert, J. (2018).
18
F-labelling innovations and their potential for clinical application. Clin. Transl. Imaging 6 (3): 169–193. https://doi.org/10.1007/ s40336-018-0280-0.
20. Gillis, E.P., Eastman, K.J., Hill, M.D. etal. (2015). Applications of uorine in medicinal chem­istry. J. Med. Chem. 58 (21): 8315–8359. https://doi.org/10.1021/acs.jmedchem.5b00258.
21. Kniess, T., Laube, M., Brust, P. etal. (2015). 2-[ for building
18
F-based radiotracers for positron emission tomography. Medchemcomm
18
F]uoroethyl tosylate–a versatile tool
6 (10): 1714–1754. https://doi.org/10.1039/C5MD00303B.
Chapter 08: Fluorine-18 Radiochemistry 275
22. Vaidyanathan, G. and Zalutsky, M.R. (2006). Synthesis of N-succinimidyl 4-[18F]uo­robenzoate, an agent for labeling proteins and peptides with
18
F. Nat. Protoc. 1 (4):
1655–1661. https://doi.org/10.1038/nprot.2006.264.
23. Scott, P.J.H., Shao, X., and Automated, F. (2010). High yielding production of N-suc­cinimidyl 4-[
18
F]uorobenzoate ([18F]SFB), and its use in microwave-enhanced radio­chemical coupling reactions. J. Labelled Compd. Radiopharm. 53 (9): 586–591. https:// doi.org/10.1002/jlcr.1785.
24. Mossine, A.V., Brooks, A.F., Ichiishi, N. etal. (2017). Development of customized [
18
F] uoride elution techniques for the enhancement of copper-mediated late-stage radiouorination. Sci. Rep. 7 (1): 233. https://doi.org/10.1038/s41598-017-00110-1.
25. Lee, S.J., Makaravage, K.J., Brooks, A.F. etal. (2019). Copper-mediated aminoquino­line-directed radiouorination of aromatic C−H bonds with K
18
F. Angew. Chem. Int. Ed.
131 (10): 3151–3154. https://doi.org/10.1002/anie.201812701.
26. Gatley, S.J., Hichwa, R.D., Shaughnessy, W.J. etal. (1981).
18
F-labeled lower uoroal­kanes; reactor-produced gaseous physiological tracers. Int. J. Appl. Radiat. Isot. 32 (4): 211–214. https://doi.org/10.1016/0020-708X(81)90051-X.
27. Silver, G.S.J. (1982). Oxide assisted synthesis of uoroalkanes; measurements with a uoride electrode and with uorine-18. Int. J. Appl. Radiat. Isot. 33 (4): 255–258. https://doi.org/10.1016/0020-708X(82)90023-0.
28. Clark, J.C., Goulding, R.W., and Palmer, A.J. (1973). Radiopharmaceuticals and Labelled Compounds. London: IAEA. 411 p. https://inis.iaea.org/collection/NCLCollection­Store/_Public/05/100/5100770.pdf.
29. Shalom, E., Takrouri, K., Metsuyanim, N. etal. (2007). Semiautomated synthesis of a
18
novel [
F] amine uorocyanoborane for PET imaging studies. Radiosynthesis and in vivo characterization in rats. Appl. Radiat. Isot. 65 (2): 204–208. https://doi.org/10.1016/j .apradiso.2006.08.014.
30. Caires, C.C. and Guccione, S. (2010). Methods for silver-promoted uorination of organic molecules. US patent 8,212,090, led 10 December 2009 and issued 3 July 2012.
31. Lee, S.J., Brooks, A.F., Ichiishi, N. etal. (2019). C–H ylquinolines with Ag[
18
F]F. Chem. Commun. 55 (20): 2976–2979. http://xlink.rsc.
18
F-uorination of 8-meth-
org/?DOI=C9CC00641A.
32. Verhoog, S., Brooks, A.F., Winton, W.P. etal. (2019). Ring opening of epoxides with
18
[
F]FeF species to produce [18F]uorohydrin PET imaging agents. Chem. Commun.:
2–6. http://xlink.rsc.org/?DOI=C9CC02779C.
33. Schimler, S.D., Cismesia, M.A., Hanley, P.S. etal. (2017). Nucleophilic deoxyuorina­tion of phenols via aryl uorosulfonate intermediates. J. Am. Chem. Soc. 139 (4): 1452–1455. https://doi.org/10.1021/jacs.6b12911.
34. Sun, H. and DiMagno, S.G. (2005). Anhydrous tetrabutylammonium uoride. J. Am. Chem. Soc. 127: 2050–2051. https://doi.org/10.1021/JA0440497.
35. Cox, D.P., Terpinski, J., and Lawrynowicz, W. (1984). “Anhydrous” tetrabutylammo­nium uoride: a mild but highly ecient source of nucleophilic uoride ion. J. Org. Chem. 49 (17): 3216–3219. https://doi.org/10.1021/jo00191a035.
276 Handbook of Radiopharmaceuticals
36. Cismesia, M.A., Ryan, S.J., Bland, D.C. etal. (2017). Multiple approaches to the in situ generation of anhydrous tetraalkylammonium uoride salts for S
Ar uorination
N
reactions. J. Org. Chem. 82 (10): 5020–5026. https://doi.org/10.1021/acs.joc.7b00481.
37. Schwesinger, R., Link, R., Wenzl, P. etal. (2006). Anhydrous phosphazenium uo­rides as sources for extremely reactive uoride ions in solution. Chem. Eur. J. 12 (2): 438–445. https://doi.org/10.1002/chem.200500838.
38. Stewart, M.N., Hockley, B.G., and Scott, P.J.H. (2015). Green approaches to late-stage uorination: radiosyntheses of
18
F-labelled radiopharmaceuticals in ethanol and
water. Chem. Commun. 51: 14805. https://doi.org/10.1039/c5cc05919d.
39. Mossine, A.V., Brooks, A.F., Henderson, B.D. etal. (2017). An updated radiosynthesis
18
of [
F]AV1451 for tau PET imaging. EJNMMI Radiopharm. Chem. 2 (1): 7. https://doi.
org/10.1186/s41181-017-0027-7.
40. Sergeev, M.E., Morgia, F., Lazari, M. etal. (2015). Titania-catalyzed radiouorina­tion of tosylated precursors in highly aqueous medium. J. Am. Chem. Soc. 137 (17): 5686–5694. https://doi.org/10.1021/jacs.5b02659.
41. Wook, K.D., Ahn, D.-S., Oh, Y.-H. etal. (2006). A new class of S
2 reactions catalyzed
N
by protic solvents: facile uorination for isotopic labeling of diagnostic molecules. J. Am. Chem. Soc. 128: 16394–16397. https://doi.org/10.1021/ja0646895.
42. Wook, K.D., Jeong, H.-J., Tae, L.S. etal. (2008). Facile nucleophilic uorination reactions using tert-alcohols as a reaction medium: signicantly enhanced reactivity of alkali metal uorides and improved selectivity. J. Org. Chem. 73: 957–962. https:// doi.org/10.1021/jo7021229.
43. Lee, J.-W., Oliveira, M.T., Bin, J.H. etal. (2016). Hydrogen-bond promoted nucleophilic uorination: concept, mechanism and applications in positron emission tomography. Chem. Soc. Rev. 45 (17): 4638–4650. http://xlink.rsc.org/?DOI=C6CS00286B.
44. Turkman, N., Gelovani, J.G., and Alauddin, M.M. (2010). A novel method for stereo­specic uorination at the 2–-arabino-position of pyrimidine nucleoside: synthesis of
18
[
F]-FMAU. J. Labelled Compd. Radiopharm. 53 (13): 782–786. https://doi.org/10.1002/
jlc r.1797.
45. Kil, H.S., Cho, H.Y., Lee, S.J. etal. (2013). Alternative synthesis for the preparation of
18
16α-[
F]uoroestradiol. J. Labelled Compd. Radiopharm. 56 (12): 619–626. https://doi
.org/10.1002/jlcr.3076.
46. Kiesewetter, D.O., Kilbourn, M.R., Landvatter, S.W. etal. (1984). Preparation of four uorine-18-labeled estrogens and their selective uptakes in target tissues of immature rats. J. Nucl. Med. 25 (11): 1212–1221. http://jnm.snmjournals.org/ content/25/11/1212.full.pdf.
47. Knott, K.E., Grätz, D., Hübner, S. etal. (2011). Simplied and automatic one-pot syn­thesis of 16α-[
18
F]uoroestradiol without high-performance liquid chromatography purication. J. Labelled Compd. Radiopharm. 54 (12): 749–753. https://doi .org/10.1002/ jlc r.1916.
48. Amaraesekera, B., Marchis, P.D., Bobinski, K.P. etal. (2013). High-pressure, compact, modular radiosynthesizer for production of positron emitting biomarkers. Appl. Radiat. Isot. 78: 88–101. https://doi.org/10.1016/J.APRADISO.2013.04.024.
Chapter 08: Fluorine-18 Radiochemistry 277
49. Ackermann, U., Lewis, J.S., Young, K. etal. (2016). Fully automated synthesis of [18F] uoro-dihydrotestosterone ([
18
F]FDHT) using the FlexLab module. J. Labelled Compd.
Radiopharm. 59 (10): 424–428. https://doi.org/10.1002/jlcr.3417.
50. Zhou, D., Lin, M., Yasui, N. etal. (2014). Optimization of the preparation of uorine­18-labeled steroid receptor ligands 16alpha-[ furanyl norprogesterone (FFNP), and 16beta-[
18
F]uoroestradiol (FES), [18F]uoro
18
F]uoro-5alpha-dihydrotestosterone (FDHT) as Ra. J. Labelled Compd. Radiopharm. 57 (5): 371–377. https://doi.org/10.1002/ jlcr. 3191.
51. Revunov, E. and Zhuravlev, F. (2013). Co(salen)-mediated enantioselective radio­uorination of epoxides. Radiosynthesis of enantiomerically enriched [
18
F]F-MISO via kinetic resolution. J. Fluorine Chem. 156: 130–135. https://doi.org/10.1016/j. juchem.2013.09.006.
52. Graham, T.J.A., Lambert, R.F., Ploessl, K. etal. (2014). Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [
18
F]uorohydrins. J. Am.
Chem. Soc. 136 (14): 5291–5294. https://doi.org/10.1021/ja5025645.
53. Huang, X., Liu, W., Ren, H. etal. (2014). Late stage benzylic C-H uorination with
18
[
F]uoride for PET imaging. J. Am. Chem. Soc. 136 (19): 6842–6845. https://doi.
org/10.1021/ja5039819.
54. Carroll, L., Evans, H.L., Spivey, A.C. etal. (2015). Mn–Salen catalysed benzylic C–H activation for the synthesis of aryl[
18
F]CF3-containing PET probes. Chem. Commun. 51
(40): 8439–8441. https://doi.org/10.1039/C4CC05762G.
55. Topczewski, J.J., Tewson, T.J., and Nguyen, H.M. (2011). Iridium-catalyzed allylic uo­rination of trichloroacetimidates. J. Am. Chem. Soc. 133 (48): 19318–19321.
56. Braun, M.-G. and Doyle, A.G. (2013). Palladium-catalyzed allylic C–H uorination. J. Am. Chem. Soc. 135 (35): 12990–12993. https://doi.org/10.1021/ja407223g.
57. Hollingworth, C., Hazari, A., Hopkinson, M.N. etal. (2011). Palladium-catalyzed allylic uorination. Angew. Chem. Int. Ed. 50 (11): 2613–2617. https://doi.org/10.1002/ anie.201007307.
58. Benedetto, E., Tredwell, M., Hollingworth, C. etal. (2013). Regio- and stereoretentive synthesis of branched, linear (E)-and (Z)-allyl uorides from allyl carbonates under Ir-catalysis. Chem. Sci. 4: 89–96. https://doi.org/10.1039/C2SC21789A.
59. Mixdorf, J.C., Sorlin, A.M., Dick, D.W. etal. (2019). Iridium-catalyzed radiosynthesis of branched allylic [
60. Angelini, G., Speranza, M., Wolf, A.P. etal. (1990). on a,a,a-trihalotoluenes. A useful route to no-carrier-added (NCA)
18
F]uorides. Org. Lett. 21 (1): 60–64.
18
F-to-halogen exchange reaction
18
F-labeled sub­stituted a,a,a-triuorotoluenes. Radiochim. Acta 50: 63–69. https://doi.org/10.1524/ ract.1990.50.12.63.
61. Angelini, G., Speranza, M., Shiue, C.-Y. etal. (1986). H
18
F + Sb2O3: a new selective radio­uorinating agent. J. Chem. Soc., Chem. Commun. 12: 924. https://doi.org/10.1039/ c39860000924.
62. Kilbourn, M.R., Pavia, M.R., and Gregor, V.E. (1990). Synthesis of uorine-18 Labeled GABA uptake inhibitors. Int. J. Radiat. Appl. Instrumentation. Part A. Appl. Radiat. Isot. 41 (9): 823–828. https://doi.org/10.1016/0883-2889(90)90059-P.
278 Handbook of Radiopharmaceuticals
63. Verhoog, S., Pfeifer, L., Khotavivattana, T. etal. (2016). Silver-mediated 18F-label­ing of aryl-CF
and aryl-CHF2 with 18F-uoride. Synlett 27 (01): 25–28. https://doi.
3
org/10.1055/s-0035-1560592.
64. Riss, P.J., Aigbirhio, F.I., and Simple, A. (2011). Rapid procedure for nucleophilic radio­synthesis of aliphatic [
18
F]triuoromethyl groups. Chem. Commun. 47 (43): 11873.
https://doi.org/10.1039/c1cc15342k.
65. Riss, P.J., Ferrari, V., Brichard, L. etal. (2012). Direct, nucleophilic radiosynthesis of
18
[
F]triuoroalkyl tosylates: improved labelling procedures. Org. Biomol. Chem. 10
(34): 6980. https://doi.org/10.1039/c2ob25802a.
66. Shao, X., Schnau, P.L., Fawaz, M.V. etal. (2013). Enhanced radiosyntheses of [ pride and [
11
C]DASB using ethanolic loop chemistry. Nucl. Med. Biol. 40 (1): 109–116.
11
C]raclo-
https://linkinghub.elsevier.com/retrieve/pii/S0969805112002533.
67. Khotavivattana, T., Verhoog, S., Tredwell, M. etal. (2015). , -OCF
and -OCHF2 with [18F]uoride. Angew. Chem. Int. Ed. 127 (34): 10129–10133.
3
18
F-labeling of aryl-SCF3
https://doi.org/10.1002/ange.201504665.
68. Zheng, J., Wang, L., Lin, J.-H. etal. (2015). Diuorocarbene-derived triuoromethyl­thiolation and [
18
F]triuoromethylthiolation of aliphatic electrophiles. Angew. Chem.
Int. Ed. 54 (45): 13236–13240. https://doi.org/10.1002/anie.201505446.
69. Zheng, J., Cheng, R., Lin, J.-H. etal. (2017). An unconventional mechanistic insight into SCF
formation from diuorocarbene: preparation of 18F-labeled α-SCF3 car-
3
bonyl compounds. Angew. Chem. Int. Ed. 56 (12): 3196–3200. https://doi.org/10.1002/ anie.201611761.
70. Verhoog, S., Kee, C.W., Wang, Y. etal. (2018). peptides with 5-
18
F-(Triuoromethyl)dibenzothiophenium triuoromethanesulfo-
18
F-triuoromethylation of unmodied
nate. J. Am. Chem. Soc. 140 (5): 1572–1575. https://doi.org/10.1021/jacs.7b10227.
71. Huiban, M., Tredwell, M., Mizuta, S. etal. (2013). A broadly applicable [
18
F]triuo­romethylation of aryl and heteroaryl iodides for PET imaging. Nat. Chem. 5 (11): 941–944. https://doi.org/10.1038/nchem.1756.
72. Rühl, T., Raque, W., Lien, V.T. etal. (2014). Cu(I)-mediated arenes: rapid synthesis of
18
F-labeled triuoromethyl arenes. Chem. Commun. 50 (45):
18
F-triuoromethylation of
6056–6059. https://doi.org/10.1039/C4CC01641F.
73. Van Der Born, D., Herscheid, J.D.M., Orru, R.V.A. etal. (2013). Ecient synthesis of
18
[
F]triuoromethane and its application in the synthesis of PET tracers. Chem. Com-
mun. 49 (38): 4018–4020. https://doi.org/10.1039/c3cc37833k.
74. van der Born, D., Sewing, C., Herscheid, J.K.D.M. etal. (2014). A universal procedure for the [
18
F]triuoromethylation of aryl iodides and aryl Boronic acids with highly improved specic activity. Angew. Chem. Int. Ed. 53 (41): 11046–11050. https://doi. org/10.1002/anie.201406221.
75. Ivashkin, P., Lemonnier, G., Cousin, J. etal. (2014). [
18
F]CuCF3: a [ 18F]triuoromethyl­ating agent for arylboronic acids and aryl iodides. Chem. Eur. J. 20 (31): 9514–9518. https://doi.org/10.1002/chem.201403630.
76. Fawaz, M.V., Brooks, A.F., Rodnick, M.E. etal. (2014). High anity radiopharmaceu­ticals based upon lansoprazole for PET imaging of aggregated tau in Alzheimer’s
Chapter 08: Fluorine-18 Radiochemistry 279
disease and progressive supranuclear palsy: synthesis, preclinical evaluation, and lead selection. ACS Chem. Neurosci. 5 (8): 718–730. https://doi.org/10.1021/ cn500103u.
77. Kramer, V., Brooks, A.F., Haeger, A. etal. (2020). Evaluation of [
18
F]-N -methyl lanso­prazole as a tau PET imaging agent in rst-in-human studies. ACS Chem. Neurosci 11 (3): 427–435.
78. Khotavivattana, T., Verhoog, S., Tredwell, M. etal. (2015).
-OCF
and -OCHF2 with [18F]uoride. Angew. Chem. Int. Ed. 54 (34): 9991–9995. https://
3
18
F-Labeling of aryl-SCF3,
doi.org/10.1002/anie.201504665.
79. Brooks, A.F., Drake, L.R., Shao, X. etal. (2018). Evaluation of enzyme substrate radio­tracers as PET/MRS hybrid imaging agents. ACS Med. Chem. Lett. 9 (11): 1140–1143. https://doi.org/10.1021/acsmedchemlett.8b00402.
80. Shi, H., Braun, A., Wang, L. etal. (2016). Synthesis of
18
F-diuoromethylarenes from aryl (pseudo) halides. Angew. Chem. Int. Ed. 55 (36): 10786–10790. https://doi. org/10.1002/anie.201604106.
81. Yuan, G., Wang, F., Stephenson, N.A. etal. (2017). Metal-free
18
F-labeling of aryl-CF2H via nucleophilic radiouorination and oxidative C–H activation. Chem. Commun. 53 (1): 126–129. http://xlink.rsc.org/?DOI=C6CC07913J.
82. Zeng, X., Li, J., Ng, C.K. etal. (2018). (Radio)Fluoroclick reaction enabled by a hydrogen-bonding cluster. Angew. Chem. Int. Ed. 57 (11): 2924–2928. https://doi. org/10.1002/anie.201711341.
83. Thompson, S., Onega, M., Ashworth, S. etal. (2015). A two-step uorinase fnzyme mediated
18
F labelling of an RGD peptide for positron emission tomography. Chem.
Commun. 51 (70): 13542–13545. https://doi.org/10.1039/C5CC05013H.
84. Zhou, Y., Wang, J., Gu, Z. etal. (2016). Next generation of uorine-containing pharma­ceuticals, compounds currently in phase II–III clinical trials of major pharmaceutical companies: new structural trends and therapeutic areas. Chem. Rev. 116 (2): 422–518. https://doi.org/10.1021/acs.chemrev.5b00392.
85. Wang, J., Sánchez-Roselló, M., Aceña, J.L. etal. (2014). Fluorine in pharmaceutical industry: uorine-containing drugs introduced to the market in the last decade (2001–2011). Chem. Rev. 114 (4): 2432–2506. https://doi.org/10.1021/cr4002879.
86. Shah, P. and Westwell, A.D. (2007). The role of uorine in medicinal chemistry. J. Enzyme Inhib. Med. Chem. 22 (5): 527–540. http://www.tandfonline.com/doi/ full/10.1080/14756360701425014.
87. Müller, K. and Böhm, H.-J. (2009). Facilitating the design of uorinated drugs. Chem. Biol. 16 (11): 1130–1131. https://doi.org/10.1016/J.CHEMBIOL.2009.11.004.
88. Mei, H., Han, J., Fustero, S. etal. (2019). Fluorine-containing drugs approved by the FDA in 2018. Chem. A Eur. J. 25 (51): 11797–11819. https://onlinelibrary.wiley.com/doi/ abs/10.1002/chem.201901840.
89. Sander, K., Galante, E., Gendron, T. etal. (2015). Development of uorine-18 labeled metabolically activated tracers for imaging of drug eux transporters with positron emission tomography. J. Med. Chem. 58 (15): 6058–6080. https://doi.org/10.1021/acs. jmedchem.5b00652.
280 Handbook of Radiopharmaceuticals
90. Zlatopolskiy, B.D., Zischler, J., Krapf, P. etal. (2015). Copper-mediated aromatic radiouorination revisited: ecient production of PET tracers on a preparative scale. Chem. Eur. J. 21 (15): 5972–5979. https://doi.org/10.1002/chem.201405586.
91. Snyder, S.E. and Kilbourn, M.R. (2005). Chemistry of uorine-18 radiopharmaceuti­cals. In: Handbook of Radiopharmaceuticals, 195–227. Chichester, UK: Wiley. Avail­able from: https://doi.org/10.1002/0470846380.ch6.
92. Moore, T.M., Akula, M.R., Collier, L. etal. (2013). A rapid microuidic synthesis of
18
[
F]uoroarenes from nitroarenes. Appl. Radiat. Isot. 71 (1): 47–50. https://doi.
org/10.1016/J.APRADISO.2012.09.013.
93. Pike, V.W. and Aigbirhio, F.I. (1995). Reactions of cyclotron-produced [ with diaryliodonium salts—a novel single-step route to no-carrier-added [
18
F]uoride
18
F]uo­roarenes. J. Chem. Soc., Chem. Commun. 21: 2215–2216. https://doi.org/10.1039/ C39950002215.
94. Pike, V.W. (2018). Hypervalent aryliodine compounds as precursors for radiouo­rination. J. Labelled Compd. Radiopharm. 61 (3): 196–227. https://doi.org/10.1002/ jlcr.3570.
95. Shah, A., Pike, V.W., and Widdowson, D.A. (1998). The synthesis of [ from the reaction of cyclotron-produced [
18
F]uoride ion with diaryliodonium salts.
18
F]uoroarenes
J. Chem. Soc. Perkin Trans. 1 13: 2043–2046. https://doi.org/10.1039/a802349b.
96. Krzyczmonik, A., Keller, T., López-Picón, F.R. etal. (2019). Radiosynthesis and pre­clinical evaluation of an α2A-adrenoceptor tracer candidate, 6-[
18
F]uoro-marsani-
dine. Mol. Imaging Biol. 21 (5): 879–887. https://doi.org/10.1007/s11307-019-01317-6.
97. Bergman, J. and Solin, O. (1997). Fluorine-18-labeled uorine gas for synthesis of tracer molecules. Nucl. Med. Biol. 24 (7): 677–683. https://doi.org/10.1016/S0969­8051(97)00078-4.
98. Stenhagen, I.S.R., Kirjavainen, A.K., Forsback, S.J. etal. (2013). [ an arylboronic ester using [
18
F]selectuor bis(triate): application to 6-[18F]uoro-l-
18
F]uorination of
DOPA. Chem. Commun. 49 (14): 1386. https://doi.org/10.1039/c2cc38646a.
99. Teare, H., Robins, E.G., Kirjavainen, A. etal. (2010). Radiosynthesis and evaluation
18
of [
F]selectuor bis(triate). Angew. Chem. Int. Ed. 49 (38): 6821–6824. https://doi.
org/10.1002/anie.201002310.
100. Teare, H., Robins, E.G., Årstad, E. etal. (2007). Synthesis and reactivity of [
18
F]­N-uorobenzenesulfonimide. Chem. Commun. 23: 2330–2332. https://doi. org/10.1039/B701177F.
101. Sun, H. and DiMagno, S.G. (2007). Competitive demethylation and substitution in N,N,N-trimethylanilinium uorides. J. Fluorine Chem. 128 (7): 806–812. https://doi. org/10.1016/J.JFLUCHEM.2007.03.009.
102. Lazarova, N., Siméon, F.G., Musachio, J.L. etal. (2007). Integration of a microwave reactor with synthia to provide a fully automated radiouorination module. J. Labelled Compd. Radiopharm. 50 (5–6): 463–465. https://doi.org/10.1002/jlcr.1196.
103. Iovkova, L., Wängler, B., Schirrmacher, E. etal. (2009). para -functionalized aryl-di­tert-butyluorosilanes as potential labeling synthons for
18
F radiopharmaceuticals.
Chem. Eur. J. 15 (9): 2140–2147. https://doi.org/10.1002/chem.200802266.
Chapter 08: Fluorine-18 Radiochemistry 281
104. Naumiec, G.R., Cai, L., Lu, S. etal. (2017). Quinuclidine and DABCO enhance the radiouorination of 5-substituted 2-halopyridines. Eur. J. Org. Chem. 2017 (45): 6593–6603. https://doi.org/10.1002/ejoc.201700970.
105. Kwon, Y.-D., Son, J., and Chun, J.-H. (2018). Catalyst-free aromatic radiouorina­tion via oxidized Iodoarene precursors. Org. Lett. 20 (24): 7902–7906. https://doi. org/10.1021/acs.orglett.8b03450.
106. Narayanam, M., Ma, G., Champagne, P. etal. (2018). Nucleophilic
18
F-uorination of anilines via N-arylsydnone intermediates. Synlett 29 (09): 1131–1135. http://www. thieme-connect.de/DOI/DOI?10.1055/s-0036-1591948.
107. Mu, L., Fischer, C.R., Holland, J.P. etal. (2012).
18
F-radiolabeling of aromatic com­pounds using triarylsulfonium salts. Eur. J. Org. Chem. 2012 (5): 889–892. https:// doi.org/10.1002/ejoc.201101730.
108. Sander, K., Gendron, T., Yiannaki, E. etal. (2015). Sulfonium salts as leaving groups for aromatic labelling of drug-like small molecules with uorine-18. Sci. Rep. 5 (1):
9941. https://doi.org/10.1038/srep09941.
109. Gendron, T., Sander, K., Cybulska, K. etal. (2018). Ring-closing synthesis of dibenzo­thiophene sulfonium salts and their use as leaving groups for aromatic
18
F-uorina-
tion. J. Am. Chem. Soc. 140 (35): 11125–11132. https://doi.org/10.1021/jacs.8b06730.
110. Recent, O.S. (2001). Progress in uorine-18 labelled peptide radiopharmaceuticals. Eur. J. Nucl. Med. 28 (7): 929–938. https://doi.org/10.1007/s002590100508.
111. Becaud, J., Mu, L., Karramkam, M. etal. (2009). Direct one-step
18
F-labeling of pep­tides via nucleophilic aromatic substitution. Bioconjugate Chem. 20 (12): 2254–2261. https://doi.org/10.1021/bc900240z.
112. Ermert, J., Hocke, C., Ludwig, T. etal. (2004). Comparison of pathways to the versa­tile synthon of no-carrier-added 1-bromo-4-[
18
F]uorobenzene. J. Labelled Compd.
Radiopharm. 47 (7): 429–441. https://doi.org/10.1002/jlcr.830.
113. Basuli, F., Zhang, X., Woodroofe, C.C. etal. (2017). Fast indirect uorine-18 labeling of protein/peptide using the useful 6-uoronicotinic acid-2,3,5,6-tetrauorophenyl prosthetic group: a method comparable to direct uorination. J. Labelled Compd. Radiopharm. 60 (3): 168–175. https://doi.org/10.1002/jlcr.3487.
114. Prante, O., Maschauer, S., and Banerjee, A. (2013). Radioligands for the dopamine receptor subtypes. J. Labelled Compd. Radiopharm. 56 (3–4): 130–148. https://doi. org/10.1002/jlcr.3000.
115. Preshlock, S., Calderwood, S., Verhoog, S. etal. (2016). Enhanced copper­mediated
18
F-uorination of aryl boronic esters provides eight radiotracers for PET applications. Chem. Commun. 52 (54): 8361–8364. https://doi.org/10.1039/ C6CC03295H.
116. Carroll, M.A., Nairne, J., and Woodcraft, J.L. (2007). Diaryliodonium salts: a solution
18
to 3-[
F]uoropyridine. J. Labelled Compd. Radiopharm. 50 (5–6): 452–454. https://
doi.org/10.1002/jlcr.1190.
117. Yuan, Z., Cheng, R., Chen, P. etal. (2016). Ecient pathway for the preparation of aryl(isoquinoline)iodonium(III) salts and synthesis of radiouorinated isoquinolines. Angew. Chem. Int. Ed. 55 (39): 11882–11886. https://doi.org/10.1002/anie.201606381.
282 Handbook of Radiopharmaceuticals
118. Chun, J.-H., Lu, S., and Pike, V.W. (2011). Rapid and ecient radiosyntheses of meta-substituted [
18
F]uoroarenes from [18F]uoride ion and diaryliodonium­tosylates within a microreactor. Eur. J. Org. Chem. 2011 (23): 4439–4447. https://doi. org/10.1002/ejoc.201100382.
119. Ross, T.L., Ermert, J., Hocke, C. etal. (2007). Nucleophilic
18
F-uorination of hetero­aromatic iodonium salts with no-carrier-added [18F]uoride. J. Am. Chem. Soc. 129: 8018–8025. https://doi.org/10.1021/JA066850H.
120. Yamada, Y. and Okawara, M. (1972). Steric eect in the nucleophilic attack of bromide anion on diaryl- and aryl-2-thienyliodonium ions. Bull. Chem. Soc. Jpn. 45 (6): 1860–1863. https://doi.org/10.1246/bcsj.45.1860.
121. Yamada, Y., Kashima, K., and Okawara, M. (1974). Substituent eect in the nucleo­philic attack by the bromide ion on the p -tolyl-substituted phenyliodonium ions. Bull. Chem. Soc. Jpn. 47 (12): 3179–3180. https://doi.org/10.1246/bcsj.47.3179.
122. Lancer, K.M. and Wiegand, G.H. (1976). The ortho eect in the pyrolysis of iodonium halides. A case for a sterically controlled nucleophilic aromatic (SN) substitution reaction. J. Org. Chem. 41 (21): 3360–3364. https://doi.org/10.1021/jo00883a004.
123. Chun, J.-H., Lu, S., Lee, Y.-S. etal. (2010). Fast and high-yield microreactor syntheses of ortho-substituted [
18
F]uoroarenes from reactions of [ 18F]uoride ion with diaryliodonium salts. J. Org. Chem. 75 (10): 3332–3338. https://doi.org/10.1021/ jo100361d.
124. Ichiishi, N., Brooks, A.F., Topczewski, J.J. etal. (2014). Copper-catalyzed [
18
F]uo­rination of (Mesityl)(aryl)iodonium salts. Org. Lett. 16 (12): 3224–3227. https://doi. org/10.1021/ol501243g.
125. Neumann, C.N., Hooker, J.M., and Ritter, T. (2016). Concerted nucleophilic aromatic substitution with
19F−
and 18F−. Nature 534 (7607): 369–373. https://doi.org/10.1038/
natur e176 67.
126. Vāvere, A.L., Neumann, K.D., Butch, E.R. etal. (2018). Improved, one-pot synthesis
18
of 6-[
F]uorodopamine and quality control testing for use in patients with neuroblastoma. J. Labelled Compd. Radiopharm. 61 (14): 1069–1080. https://doi. org/10.1002/jlcr.3685.
127. Edwards, R., Westwell, A.D., Daniels, S. etal. (2015). Convenient synthesis of dia­ryliodonium salts for the production of [
18
F]F-DOPA. Eur. J. Org. Chem. 2015 (3):
625–630. https://doi.org/10.1002/ejoc.201403378.
128. Jang, K.S., Jung, Y.-W., Sherman, P.S. etal. (2013). Synthesis and bioevaluation of
18
[
F]4-uoro-m-hydroxyphenethylguanidine ([18F]4F-MHPG): a novel radiotracer for quantitative PET studies of cardiac sympathetic innervation. Bioorg. Med. Chem. Lett. 23 (6): 1612–1616. https://doi.org/10.1016/J.BMCL.2013.01.106.
129. Rael, D.M., Jung, Y.-W., Koeppe, R.A. etal. (2018). First-in-human studies of [
18
F] uorohydroxyphenethylguanidines. Circ. Cardiovasc. Imaging 11 (12) https://doi. org / 10.1161/CIRCIMAGING .118.0 07965.
130. Warnier, C., Lemaire, C., Becker, G. etal. (2016). Enabling ecient positron emission tomography (PET) imaging of synaptic vesicle glycoprotein 2A (SV2A) with a robust and one-step radiosynthesis of a highly potent
18
F-labeled ligand
Chapter 08: Fluorine-18 Radiochemistry 283
([18F]UCB-H). J. Med. Chem. 59 (19): 8955–8966. https://doi.org/10.1021/acs. jmedchem.6b00905.
131. Xu, R., Zanotti-Fregonara, P., Zoghbi, S.S. etal. (2013). Synthesis and evaluation in monkey of [ benzamide ([
18
F]4-uoro-N-methyl-N -(4-(6-[methylamino]pyrimidin-4-yl)thiazol-2-yl)
18
F]FIMX): a promising radioligand for PET imaging of brain metabo­tropic glutamate recept. J. Med. Chem. 56 (22): 9146–9155. https://doi.org/10.1021/ jm4012017.
132. Lee, E., Kamlet, A.S., Powers, D.C. etal. (2011). A uoride-derived electrophilic late­stage uorination reagent for PET imaging. Science 334 (6056): 639–642. https:// doi.org/10.1126/science.1212625.
133. Selivanova, S.V., Stellfeld, T., Heinrich, T.K. etal. (2013). Design, synthesis, and initial evaluation of a high anity positron emission tomography probe for imaging matrix metalloproteinases 2 and 9. J. Med. Chem. 56 (12): 4912–4920. https://doi. org/10.1021/jm400156p.
134. Chun, J.-H. and Pike, V.W. (2013). Single-step syntheses of no-carrier-added func­tionalized [
18
F]uoroarenes as labeling synthons from diaryliodonium salts. Org.
Biomol. Chem. 11 (37): 6300. https://doi.org/10.1039/c3ob41353e.
135. Irving, H. and Reid, R.W. (1960). 421. The photochemical decomposition of diphe­nyliodonium iodide. J. Chem. Soc. (0): 2078. https://doi.org/10.1039/jr9600002078.
136. Zhang, M.-R., Kumata, K., and Suzuki, K. (2007). A practical route for synthesizing a PET ligand containing [
18
with [
F]F−. Tetrahedron Lett. 48 (49): 8632–8635. https://doi.org/10.1016/J.TET-
18
F]uorobenzene using reaction of diphenyliodonium salt
LET.2007.10.025.
137. Haskali, M.B., Telu, S., Lee, Y.-S. etal. (2016). An investigation of (Diacetoxyiodo) arenes as precursors for preparing no-carrier-added [ cyclotron-produced [
18
F]uoride ion. J. Org. Chem. 81 (1): 297–302. https://doi.
18
F]uoroarenes from
org/10.1021/acs.joc.5b02332.
138. McCammant, M.S., Thompson, S., Brooks, A.F. etal. (2017). Cu-mediated C–H
18
F-u­orination of electron-rich (hetero)arenes. Org. Lett. 19 (14): 3939–3942. https://doi. org/10.1021/acs.orglett.7b01902.
139. Satyamurthy, N. and Barrio, J.R. (2010). No-carrier-added nucleophilic [F-18] uori­nation of aromatic compounds. International patent WO/2010/117435.
140. Rotstein, B.H., Stephenson, N.A., Vasdev, N. etal. (2014). Spirocyclic hypervalent iodine(III)-mediated radiouorination of non-activated and hindered aromatics. Nat. Commun. 5 (1): 4365. https://doi.org/10.1038/ncomms5365.
141. Jakobsson, J.E., Grønnevik, G., and Riss, P.J. (2017). Organocatalyst-assisted Ar–
18
F bond formation: a universal procedure for direct aromatic radiouorination. Chem. Commun. 53 (96): 12906–12909. https://doi.org/10.1039/C7CC07211B.
142. Rotstein, B.H., Wang, L., Liu, R.Y. etal. (2016). Mechanistic studies and radiouori­nation of structurally diverse pharmaceuticals with spirocyclic Iodonium(III) ylides. Chem. Sci. 7 (7): 4407–4417. https://doi.org/10.1039/C6SC00197A.
143. Calderwood, S., Collier, T.L., Gouverneur, V. etal. (2015). Synthesis of 18F-arenes from spirocyclic iodonium(III) ylides via continuous-ow microuidics. J. Fluorine Chem. 178: 249–253. https://doi.org/10.1016/J.JFLUCHEM.2015.08.006.
284 Handbook of Radiopharmaceuticals