Abstract
The synthesis of a new rigid analogue of cyclohexyl-TTHA, an
efficient lanthanide ligand, as well, as the first complexation
trials are reported. This polyaminopolycarboxylic acid, Ph-DTHA 1 , was obtained in five steps from phenylenediamine
as starting product. The key intermediate was phenylenediethylenetetraamine 4 , which after alkylation and hydrolysis
gave the expected compound 1 with ten coordination
centers.
Key words
ligands - polyaminopolycarboxylic acids - radioimmunotherapy - complexes - radionuclides
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15 Spectrum data of compound 1 : IR (KBr): 3419, 2970, 1733, 1635, 1418,
1256 cm-1 ; 1 H NMR
(200 MHz, D2 O): δ = 3.49 [4
H, m, 2 × NCH2 CH
2 N(CH2 CO2 H)2 ],
3.69 (4 H, m, 2 × NCH
2 CH2 N(CH2 CO2 H)2 ),
4.09 [4 H, s, 2 × N(CH
2 CO2 H)], 4.19 [8
H, s, 2 × N(CH
2
CO2 H)2 ],
7.13 (4 H, m, CH ar);13 C
NMR (50 MHz, D2 O): δ = 50.4 [2 × NCH2
C H2 N(CH2 CO2 H)2 ],
56.5 [2 × NC H2 CH2 N(CH2 CO2 H)2 ],
57.3 [2 × N(C H2 CO2 H)],
58.5 [2 × N(C H2 CO2 H)2 ],
125.7 [2 × C Har],
128.8 [2 × C Har],
145.0 [2 × C ar],
171.9 [4 × N(CH2
C O2 H)2 ],
178.2 [2 × N(CH2
C O2 H)];
MS (ES+): = 543.1 (M + H+ ),
565.1 (M + Na+ ); mp >300 °C.
