Synthesis and chemical reactivity of a 6-Me-3,2-hydroxypyridinone dithiazolide with primary amines: a route to new hexadentate chelators for hard metal(III) ions.
A hydroxypyridinone building block, bifunctionalized with thiazoline, has been prepared from orthogonally protected 2-(3-(benzyloxy)-4-(ethoxycarbonyl)-6-methyl-2-oxopyridin-1(2H)-yl) acetic acid. The reactivity of the dithiazolide has been explored with two primary amines, leading to the synthesis and characterization of four new hexadentate ligands. Their complexes with selected hard trivalent ions pertinent to potential molecular imaging applications have been surveyed.
Department of Chemistry, University of California, Berkeley, California 94720-1460.
Sylvie L
SL
Pailloux
Department of Chemistry, University of California, Berkeley, California 94720-1460.
Sean
S
Nguyen
Department of Chemistry, University of California, Berkeley, California 94720-1460.
Stephanie
S
Zhou
Department of Chemistry, University of California, Berkeley, California 94720-1460.
Marisa E
ME
Hom
Department of Chemistry, University of California, Berkeley, California 94720-1460.
Michelle N
MN
Keyser
Department of Chemistry, University of California, Berkeley, California 94720-1460.
Danil
D
Smiles
Department of Chemistry, University of California, Berkeley, California 94720-1460.
Kenneth N
KN
Raymond
Synthesis (Stuttg). 2011 Jan 1;2011(1):57-64
21709749
Bioconjug Chem. 2005 Jan-Feb;16(1):3-8
15656568
Inorg Chem. 2004 Dec 27;43(26):8520-5
15606201
Metallomics. 2014 Feb;6(2):249-62
23999879
J Am Chem Soc. 2011 Mar 2;133(8):2390-3
21294571
J Am Chem Soc. 2007 Feb 21;129(7):1870-1
17260995
Contrast Media Mol Imaging. 2009 Sep-Oct;4(5):220-9
19839031
J Org Chem. 2009 Jan 16;74(2):782-8
19063593
J Am Chem Soc. 2010 Nov 10;132(44):15525-7
20958067
J Am Chem Soc. 2004 Jul 14;126(27):8388-9
15237990
Inorg Chem. 2004 Dec 27;43(26):8577-86
15606209
Inorg Chem. 2003 Aug 11;42(16):4930-7
12895117
J Med Chem. 2005 Jun 2;48(11):3874-7
15916439
Chem Pharm Bull (Tokyo). 1983 Mar;31(3):852-60
6883608
J Comb Chem. 2005 May-Jun;7(3):490-502
15877478
J Inorg Biochem. 2009 Apr;103(4):496-502
19195710
J Am Chem Soc. 1977 Oct 12;99(21):7014-9
561812
Tetrahedron Lett. 2013 Feb 13;54(7):630-634
23355751
Inorg Chem. 2010 Nov 1;49(21):9928-39
20873782
Acc Chem Res. 2009 Apr 21;42(4):542-52
19323456
J Am Chem Soc. 2011 Sep 21;133(37):14704-9
21800868
J Am Chem Soc. 2005 Jan 19;127(2):504-5
15643857
Biochim Biophys Acta. 2012 Mar;1820(3):282-90
22155077