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Synthesis of 3,7-Dihydroxy-3,7-dioxopenhydro-1,5,3,7-diazadiphosphocines with Various Amines
Corresponding Author(s) : D.I. Jung
Asian Journal of Chemistry,
Vol. 26 No. 3 (2014): Vol 26 Issue 3
Abstract
As a part of a research program related to the synthetic study of pharmacologically interesting compounds and good chelating agent for transition metal ion, we here report the synthesis of an unusual medium-sized ring heterocyclic ligand with mixed carboxylic-amino-phosphonic donating groups. We have synthesized 1,5-diphenyl-3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine (4a), 1,5-di(2-ethaneamine)yl-3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7- diazadiphosphocine (4b), 1,5-dibenzoic acid-yl-3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine (4c), 1,5-difurfuryl-3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine (4d), 1,5-di[thiophene-2ylmethyl]-3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine (4e), 1,5-di[thiophene-2yl]-3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine (4f), 1,5-dipyridin-4-yl-3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine (4g), 3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine-1,5-diacetic acid (4h), 2-[5-(1,2-dicarboxyethyl-3,7-dihydroxy-3,7,dioxo-315.715-[1,5,3,7]diazadiphosphocan-1-yl]-succinic acid (4i) and 3,7-Dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine-1,5-di-(2-glutaric acid) (4j).
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References
P. Caravan, J.J. Ellison, T.J. McMurry and R.B. Lauffer, Chem. Rev., 99, 2293 (1999); doi:10.1021/cr980440x.
W.A. Volkert and T.J. Hoffman, Chem. Rev., 99, 2269 (1999); doi:10.1021/cr9804386.
M.H.V. Werts, R.H. Woudenberg, P.G. Emmerink, R. van Gassel, J.W. Hofstraat and J.W. Verhoeven, Angew. Chem. Int. Ed., 39, 4542 (2000); doi:10.1002/1521-3773(20001215)39:24<4542::AID-ANIE4542>3.0.CO;2-C.
I.F. Pickersgill and H. Rapoport, J. Org. Chem., 65, 4048 (2000); doi:10.1021/jo000071g.
J.A.K. Howard, A.M. Kenwright, J.M. Moloney, D. Parker, M. Woods, J.A.K. Howard, M. Port, M. Navet and O. Rousseau, Chem. Commun., 1381 (1998); doi:10.1039/a802847h.
S. Aime, M. Botta, M. Fasano, S.G. Crich and E. Terreno, J. Biol. Inorg. Chem., 1, 312 (1996); doi:10.1007/s007750050059.
L.J.M. Kroft and A. de Roos, J. Magn. Reson. Imaging, 10, 395 (1999); doi:10.1002/(SICI)1522-2586(199909)10:3<395::AID-JMRI22>3.0.CO;2-P.
A.A. Bogdanov Jr., M. Lewin and R. Weissleder, Adv. Drug Deliv. Rev., 37, 279 (1999); doi:10.1016/S0169-409X(98)00098-2.
S.K. Choi, K.M. Bang, J.H. Song, D.H. Lee, I.S. Kim, D.I. Jung and J.T. Hahn, Asian J. Chem., 22, 3094 (2010).