Synthesis of an acromelic acid a analog-based 11C-labeled PET tracer for exploration of the site of action of acromelic acid a in allodynia induction

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 7, 2011, Pages 2017-2020

  Kanazawa, Masakatsu ^a   Furuta, Kyoji ^a   Doi, Hisashi ^b   Mori, Tomoko ^b   Minami, Toshiaki ^c   Ito, Seiji ^d   Suzuki, Masaaki ^b  

^a GIFU UNIVERSITY   (Japan)

^b RIKEN   (Japan)

^c OSAKA MEDICAL COLLEGE   (Japan)

^d KANSAI MEDICAL UNIVERSITY   (Japan)

Author keywords

Acromelic acid A; Allodynia; PET tracer

Indexed keywords

(PHENYLTHIO)PYRROLIDINE DERIVATIVE; ACROMELIC ACID A; BORONIC ACID DERIVATIVE; CARBON 11; PALLADIUM; PYRROLIDINE DERIVATIVE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ALLODYNIA; ARTICLE; DEPROTECTION REACTION; DRUG ACTIVITY; DRUG DESIGN; DRUG FORMULATION; DRUG HALF LIFE; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION EXCHANGE CHROMATOGRAPHY; METHYLATION; NONHUMAN; POSITRON EMISSION TOMOGRAPHY;

ANIMALS; HYPERALGESIA; KAINIC ACID; METHYLATION; MICE; POSITRON-EMISSION TOMOGRAPHY;

EID: 79952485461     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.02.018     Document Type: Article

References (32)

1. Saviuc, P. F.; Danel, V. C.; Moreau, P. A.; Guez, D. R.; Claustre, A. M.; Carpentier, P. H.; Mallaret, M. P.; Ducluzeau, R. J. Toxicol. Clin. Toxicol. 2001, 39, 403.
2. Konno, K.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1983, 24, 939.
3. Konnno, K.; Hashimoto, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. J. Am. Chem. Soc. 1988, 110, 4807.
4. Minami, T.; Matsumura, S.; Nishizawa, M.; Sasaguri, Y.; Hamanaka, N.; Ito, S. Br. J. Pharmacol. 2004, 142, 679.
5. Saviuc, P. F.; Danel, V. C. Toxicol. Rev. 2006, 25, 199.
6. Ito, S.; Okuda-Ashitaka, E.; Minami, T. Neurosci. Res. 2001, 41, 299.
7. Minami, T.; Matsumura, S.; Okuda-Ashitaka, E.; Shimamoto, K.; Sakimura, K.; Mishina, M.; Mori, H.; Ito, S. Brain Res. 2001, 895, 178.
8. Tsuda, M.; Shigemoto-Mogami, Y.; Koizumi, S.; Mizokoshi, A.; Kohsaka, S.; Salter, M. W.; Inoue, K. Nature 2003, 424, 778.
9. Ishida, M.; Shinozaki, H. Brain Res. 1988, 474, 386.
10. Ishida, M.; Shinozaki, H. Br. J. Pharmacol. 1991, 104, 873.
11. Kwak, S.; Aizawa, H.; Ishida, M.; Shinozaki, H. Neurosci. Lett. 1992, 139, 114.
12. Bunch, L.; Krogsgaard-Larsen, P. Med. Res. Rev. 2009, 29, 3.
13. Shinozaki, H.; Ishida, M.; Gotoh, Y.; Kwak, S. Brain Res. 1989, 503, 330.
14. Kwak, S.; Aizawa, H.; Ishida, M.; Shinozaki, H. Life Sci. 1991, 49. PL91.
15. Tsuji, K.; Nakamura, Y.; Ogata, T.; Mitani, A.; Kataoka, K.; Shibata, T.; Ishida, M.; Shinozaki, H. Neuroscience 1995, 68, 585.
16. Kwak, S.; Nakamura, R. Brain Res. 1995, 702, 61.
17. Baldwin, J. E.; Pritchard, G. J.; Williamson, D. S. Bioorg. Med. Chem. Lett. 2000, 10, 1927.
18. Baldwin, J. E.; Pritchard, G. J.; Williamson, D. S. Tetrahedron 2001, 57, 7991.
19. Soen, M.; Minami, T.; Tatsumi, S.; Mabuchi, T.; Furuta, K.; Maeda, M.; Suzuki, M.; Ito, S. Eur. J. Pharmacol. 2007, 575, 75.
20. Miller, P. W.; Long, N. J.; Vilar, R.; Gee, A. D. Angew. Chem., Int. Ed. 2008, 47, 8998.
21. Ametamey, S. M.; Honer, M.; Schubiger, P. A. Chem. Rev. 2008, 108, 1501.
22. Cai, L.; Lu, S.; Pike, V. W. Eur. J. Org. Chem. 2008, 2853.
23. Suzuki, M.; Sumi, K.; Koyama, H.; Siqin; Hosoya, T.; Takashima-Hirano, M.; Doi, H. Chem. Eur. J. 2009, 15, 12489.
24. Doi, H.; Ban, I.; Nonoyama, A.; Sumi, K.; Kuang, C.; Hosoya, T.; Tsukada, H.; Suzuki, M. Chem. Eur. J. 2009, 15, 4165.
25. Fowler, J. S.; Wolf, A. P. Acc. Chem. Res. 1997, 30, 181.
26. Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, 4th ed.; Wiley, 2007. Chapter 7.
27. Baldwin, J. E.; Bamford, S. J.; Fryer, A. M.; Rudolph, M. P. W.; Wood, M. E. Tetrahedron 1997, 53, 5233.
28. Furuta, K.; Wang, G. X.; Minami, T.; Nishizawa, M.; Ito, S.; Suzuki, M. Tetrahedron Lett. 2004, 45, 3933.
29. Nakagawa, I.; Hata, T. Tetrahedron Lett. 1975, 16, 1409.
30. Cleary, D. G. Synth. Commun. 1989, 19, 737.
31. Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392.
32. The yield of 3b was determined based on HPLC using 5-methylresorcinol as an internal standard.