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Synthesis and Characterization of Substituted Iron(II) Sulfonamides

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Presentation on theme: "Synthesis and Characterization of Substituted Iron(II) Sulfonamides"— Presentation transcript:

1 Synthesis and Characterization of Substituted Iron(II) Sulfonamides
Mattson Mathey Department of Chemistry #3838, University of Wyoming, Laramie, WY 82071 30 April 2011

2 Parent Ligand and Complex
Mn1 O1 N3 O2 N4

3 Biological Importance
6-fluoro-8-quinolinol Gershon, H. et. al.; Monatshefte fur Chemie. 2002, 133, Sveinbjornsson, A. et. al.; J. Org. Chem. 1951, 16, 1450 Elderfield, R. et al.; JACS. 1946, 68, 1524 Erhardt,S. et al; Physiol. Behav. 2007, 92, Pamaquine

4 Biological Importance
cis-[Fe(LTs)2(DMF)2] IC50=20 μM IC50=3.4 μM Values obtained from Mehn/Mandal collaboration

5 Why quinoline derived ligands?
Bidentate anionic ligands. Tunable Sterics and Electronics Using Skraup and Doebner Miller Synthesis

6 Target Ligands 8-aminotosyl-5-methylquinoline
5-Me-LTs 8-aminotosyl-6-fluoroquinoline 6-F-LTs 8-aminotosyl-6-methylquinoline 6-Me-LTs

7 General Scheme Skraup Hydrogenation Tosylation Metallation

8 Synthesis of 8-aminotosyl-6-fluoroquinoline

9 8-aminotosyl-6-fluoroquinoline
H3 Hm H2 H4 Ho H5 & H7

10 Synthesis of 8-aminotosyl-6-methylquinoline

11 8-aminotosyl-6-methylquinoline
H5 & H3 H7 Hm H2 H4 Ho

12 Synthesis of 8-aminotosyl-5-methylquinoline

13 8-aminotosyl-5-methylquinoline
Ho Hm H2 H4

14 NMR Using Paramagnetic Parameters

15 Acknowledgments I thank  Mark P. Mehn and Dylan T. Houghton
INBRE Summer Undergraduate Reseach Fellowship Wyoming EPSCoR Undergraduate Research Fellowship MPM thanks the University of Wyoming for start-up funds and Wyoming NASA Space Grant Faculty Research Initiation Grant

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