The title compound, molecular formula C30H40N10, crystallizes and exhibits a cisoidal conformation around a central p-phenylenediamine ring suggesting that this bis-tripodal ligand is highly flexible and could be accommodated by many and original metal coordinations. All four five-membered pyrazole rings are identical. The molecule presents an inversion centre that coincides with the phenyl ring centre: pyrazole rings are two-by-two equivalent. The electrostatic spatial intramolecular repulsion between N4 and N5 is probably responsible for this general arrangement. These data emphasize the basic character of nitrogens N4 and N5.
Racemic 5-aryl-and 5-(arylmethyl)tetrazolyl-substituted pyroaminoadipic and pipecolic acid derivatives were diastereoselectively synthesized from dimethyl meso-2,5-dibromoadipate (1) in good yields under mild reaction conditions. The key step of this reaction sequence is the selective N2-alkylation of 5-substituted tetrazoles with 1. The reactive 2-bromo-5-tetrazolyladipate derivatives 2a−g were generated
Five polydentate ligands 2-6 were prepared from arylamines and precursors 1a-b . The polydentate (2-4) and (5) showed marked activity against cancer cell lines. The substituents (R and R') appear to play a key role in the cytotoxic potency of this class of compounds.
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