A bidentate terephthalamide ligand, TAMmeg, as an entry into terephthalamide-containing therapeutic iron chelating agents

Inorganic Chemistry
Kristy M Clarke Jurchen, Kenneth N. Raymond

Abstract

A new bidentate 2,3-dihydroxyterephthalamide ligand, 2,3-dihydroxy-N,N'-bis(2-methoxyethyl)terephthalamide (TAMmeg), has been prepared. The ligand, its synthetic precursor 2,3-bis(benzyloxy)-N,N'-bis(2-methoxy-ethyl)-terephthalamide (BnTAMmeg), and its iron complex have been structurally characterized by X-ray diffraction. BnTAMmeg crystallizes in the monoclinic space group P2(1)/n with cell parameters a = 14.4976(14) A, b = 11.5569(11) A, c = 16.3905(16) A, beta = 113.621(1) degrees , and Z = 4. TAMmeg crystallizes in the monoclinic space group P2(1)/c with cell parameters a = 13.8060(36) A, b = 8.0049(21) A, c = 19.4346(50) A, beta = 106.855(4) degrees , and Z = 4. Fe[TAMmeg] crystallizes in the triclinic space group P with cell parameters a = 12.9565(14) A, b = 13.4514(14) A, c = 20.2092(21) A, alpha = 102.093(2) degrees , beta = 95.433(2) degrees , gamma = 101.532(2) degrees , and Z = 2. The aqueous protonation and ferric ion coordination chemistry of TAMmeg were examined using potentiometric and spectrophotometric methods. Proton association constants and iron complex formation constants for the ligand are as follows: log beta(011) = 10.32, log beta(012) = 16.49, log beta(110) = 17.9, log beta(120) = 32.1, and log beta(130...Continue Reading

References

Jan 1, 1991·Journal of Hepatology·H M KellnerH G Eckert
Dec 23, 1999·The New England Journal of Medicine·N C Andrews
Sep 1, 2001·Organic Letters·C J Gramer, K N Raymond

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Citations

Jan 14, 2009·Journal of Fluorescence·Narinder SinghJohn F Callan
Nov 5, 2011·Journal of Fluorescence·María José Casanueva MarencoJohn F Callan
Jan 6, 2015·Chemical Communications : Chem Comm·Darpan N PandyaThaddeus J Wadas
Oct 17, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Duraiyarasu MaheshwaranRamasamy Mayilmurugan

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