1978
DOI: 10.1021/ja00472a022
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Specific sequestering agents for the actinides. 1. N,N',N'',N'''-Tetra(2,3-dihydroxybenzoyl)tetraazacyclotetra- and -hexadecanes

Abstract: A new synthetic procedure is presented for the 2,3-dihydroxybenzamidation of azaalkanes. Four equivalents of 2,3-dioxomethylene (or 2,3-dimethoxybenzoyl chloride) reacted with 1,4,8,1l-tetraazacyclotetradecane (1) or 1,5,9,13-tetraazacyclohexadecane ( 2 ) to produce the corresponding cyclotetraamides (3,4,5). Subsequent treatment with either BBr3 or BCI3 in CHzCl2 solution gave the desired N,N',N'',N"'-tetra(2,3-dihydroxybenzoyl)tetraazacyclotetradecane ( 6 ) or -hexadecane (7). The latter two compounds are th… Show more

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Cited by 42 publications
(29 citation statements)
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“…In this broader role as powerful generic transition metal ligands, synthetic siderophores have been tested for in vivo radioisotope decontamination. For tetravalent ions such as Th IV and Pu IV , tetrakis‐catechol‐based ligands were specifically designed for optimal octadentate coordination and solubility in physiologic media 357–359. These ligands showed better in vivo Pu scavenging capacity than both CaNa 3 DPTA and desferrioxamine B, particularly at low actinide concentrations; moreover, the ligand was able to remove 238.…”
Section: Siderophore‐like Materialsmentioning
confidence: 99%
“…In this broader role as powerful generic transition metal ligands, synthetic siderophores have been tested for in vivo radioisotope decontamination. For tetravalent ions such as Th IV and Pu IV , tetrakis‐catechol‐based ligands were specifically designed for optimal octadentate coordination and solubility in physiologic media 357–359. These ligands showed better in vivo Pu scavenging capacity than both CaNa 3 DPTA and desferrioxamine B, particularly at low actinide concentrations; moreover, the ligand was able to remove 238.…”
Section: Siderophore‐like Materialsmentioning
confidence: 99%
“…The size of the cavity formed is controlled by the ring size of the tetraazacycloalkane backbone such that a 16 membered ring appeared most promising for the actinides. Two tetra-catechol chelating agents were synthesized from 2,3-dihydroxybenzoic acid and 1,4,8,11-tetraazacyclotetradecane or 1,5,9,13-tetraazacyclohexadecane (188). Subsequent biological evaluation in mice showed that these compounds reduced the accumulation of plutopium in bone and liver.…”
Section: Chelating Agentsmentioning
confidence: 99%
“…The nitro groups converted the ligand into an acutely active poison and substantially changed its solubility characteristics such that a large amount of plutonium was found in the soft tissues of the treated mice (97). In sharp contrast, sulfonation at the 5 position of each 2,3-dihydroxybenzoyl group in the ligands prepared above improved their water solubility, stability to air oxidation and affinity for actinide(IV) ions at low pH (190). The increased acidity of the sulfonated derivatives prevented the deposition of plutonium in the kidneys of mice and promoted significant plutonium excretion without any appreciable toxic affects (97).…”
Section: Chelating Agentsmentioning
confidence: 99%
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“…[5] One such ligand type found in siderophores are the hydroxypyridinones (HOPOs), which have been part of previous studies of actinide coordination chemistry. [6,7] A class of structural analogs to HOPOs, and the precursor to substituted 3,4-HOPO, are the hydroxypyrones, one of the simplest of which is 3-hydroxy-2-methyl-pyran-4-one (maltol, L 1 , Figure 1).…”
Section: Introductionmentioning
confidence: 99%