Synthesis of a carbon-14 analogue of N-(aryl-methyl)-3-phenyl-acryl amidine-[carboxy-14C] and its derivatives as NR2B-selective NMDA receptor antagonist
Subject Areas : Journal of the Iranian Chemical ResearchNader Saemian 1 , Kameh Esmailli 2 , Gholamhossein Shirvani 3 , Mohsen Javaheri 4 , Omid Khalili Arjomandi 5
1 - Radioisotope section / Nuclear science Research School, Nuclear Science and Technology Research
Institute, Tehran, P.O. Box: 11365-3486, Iran
2 - Radioisotope section / Nuclear science Research School, Nuclear Science and Technology Research
Institute, Tehran, P.O. Box: 11365-3486, Iran
3 - Radioisotope section / Nuclear science Research School, Nuclear Science and Technology Research
Institute, Tehran, P.O. Box: 11365-3486, Iran
4 - Radioisotope section / Nuclear science Research School, Nuclear Science and Technology Research
Institute, Tehran, P.O. Box: 11365-3486, Iran
5 - Radioisotope section / Nuclear science Research School, Nuclear Science and Technology Research
Institute, Tehran, P.O. Box: 11365-3486, Iran
Keywords: NMDA-receptor, Carbon-14, Labeling, Amidines,
Abstract :
Four amidine NR2B-selective NMDA receptor antagonists, N-( 2-methoxy benzyl) -3-phenyl-acrylamidine, N-[diduterio(2-methoxyphenyl) methyl]-3-phenyl-acrylamidine, N-benzyl-3-phenyl-acryl amidine and N-[diduterio(phenyl)methyl]-3-phenyl-acrylamidine, all fourlabeled with carbon-14 in the 1-position, have been synthesized as part of 5-step sequence fromBa14CO3.
[1] H. Mori, M. Mishina, Neuropharm 34 (1995) 1219-1237.
[2] R. Betarbet, R. Porter, J.T. Greenamyre, J. Neurochem, 74 (2000) 1166-1174.
[3] A. Buller, H. Larson, B. Schneider, J. Beaton, R. Morrisett, D. Monaghan, J. Neurosci. 14 (1994)
5471-5484.
[4] R. Dingledine, K. Borges, D. Bowie, S. Traynelis, Pharmacol. Rev. 51 (1999) 7-61.
[5] H. Monyer, N. Burnashev, D.J. Laurie, B. Sakmann, P.H. Seeburg, Neuron 12 (1994) 529-540.
[6] B.A. Chizh, P.M. Headley, T.M. Tzchentke, Trends Pharmacol Sci. 22 (2001) 636-642.
[7] S. Boyce, A. Wyatt, J.K. Webb, R.O. Donnell, G. Mason, M. Rigby, D. Sirinathsinghji, R.G. Hill,
N.M. Rupniak, Neuropharm 38 (1999) 611-623.
[8] J. Johnson, P. Ascher, Nature 325 (1987) 529-531.
[9] T. Haradahira, J. Maeda, T. Okauchi, M.R. Zhang, J. Hojo, T. Kida, T. Arai, F. Yamamato, S. Sasaki,
M. Maeda, K. Suzuki, T. Suhara, Nucl. Med. Biol. 29 (2002) 517-522.
[10] C.F. Clairborne, J.A. McCauley, B.E. Libby, N.R. Curtis, H.J. Diggle, J.J. Kulagowski, S.R.
Michelson, K.D. Anderson, D.A. Claremon, R.M. Freidinger, R.A. Bednar, S.D. Mosser, S.L. Gaul,
T.M. Connolly, C.L. Condra, B. Bednar, G.L. Stump, J.J. Lynch, A. Macaulay, K.A. Wafford, K.S.
Koblan, N.J. Liverton, Bioorg. Med. Chem. Lett. 13 (2003) 697-704.
[11] C. Thominiaux, B. Bruin, Y. Bramoulle, F. Hinnen, S. Demphel, H. Valette, M. Bottlaender, L.
Besret, M. Kassiou, F. Dolle, Appl. Radiat. Isot. 64 (2006) 343-351.
[12] N. Saemian, G. Shirvani, H. Matloubi, J. Labelled Cpd. Radiopharm. 49 (2006) 71-76.
[13] D. Seidel, P. Brehmer, Y. Schoof, U. Weinber, U. Niewohner, M. Nowakowski, J. Labelled Cpd.
Radiopharm. 46 (2003) 1019-1025.
[14] N. Saemian, G. Shirvani, S.S. Oliyaee, M. Javaheri, J. Iran. Chem. Res. 2 (2009) 63-67.
[15] N. Saemian, G. Shirvani, M. Javaheri, J. Radioanal. Nuc. Chem. 281 (2009) 421-423.
[16] N. Saemian, G. Shirvani, H. Matloubi, J. Radioanal. Nuc. Chem. 268 (2006) 545-548.
[17] J.H. Ha, J.H. Ahn, Bull. Korean Chem. Soc. 27 (2006) 121-127.
[18] J. Sandel, O. Langer, P. Larsen, F. Dolle, F. Vaufrey, S. Demphel, C. Crouzel, C. Hanlldin, J.
Labelled Cpd. Radiopharm. 43 (2000) 331-338.
[19] T.G. Hamill, J.A. McCauley, H.D. Burns, J. Labelled Cpd. Radiopharm. 48 (2005) 1-7.
[20] G. Shirvani, N. Saemian, H. Matloubi, J. Labelled Cpd. Radiopharm. 50 (2007) 1234-1235.
[21] N. Saemian, G. Shirvani, H. Matloubi, J. Radioanal. Nuc. Chem. 274 (2007) 631-633.
[22] D. Haddenham, L. Pasumansky, J. Desoto, S. Eagon, B. Singaram, J. Org. Chem. 74 (2009) 1964-
1970.
[23] N.R. Curtis, H.J. Diggle, J.J. Kulagowski, C. Londen, S. Grimwood, P.H. Hutson, F. Murray, P.
Richards, A. Macaulay, K.A. Wafford, Bioorg. Med. Chem. Lett.13 (2003) 693-698.
[24] N. Saemian, G. Shirvani, H. Matloubi, J. Radioanal. Nuc. Chem. 274 (2007) 643-646.