We have synthesized and characterized a panel of new binuclear mixed valence Cu(I,II) complexes containing substituted 2-alkylthio-5-arylmethylene-4H-imidazolin-4-ones with unusual structure. These complexes are shown to be cytotoxic for various cell lines. We have found that these compounds did not intercalate DNA, inhibited number of polymerases (telomerase predominantly), accumulated in the cell nucleus, and caused DNA degradation. Preliminary studies revealed that lead compound inhibited human breast adenocarcinoma growth in mice model.
In previous work [1], we reported the synthesis of new 1-alkyl-5-(1H-indolyl)pyrrolidin-2-ones 1 and 2, and found that these compounds do not undergo the Plancher rearrangement during their formation.However, in a continuation of this research, we found that the 1 H NMR signal at 6.88 ppm, which belongs to the indole system pyrrole ring proton in the product obtained from N-methylindole (3e) and 1-benzyl-5-hydroxypyrrolidin-2-one (4a), appears almost exactly in the middle between the signals for H-3 (6.45 ppm) and H-2 (7.26 ppm) in unsubstituted indole [2]. Thus, the spectrum does not permit us to establish the substitution pattern of the indole system, i.e., to clearly distinguish between the structures 1d and 2b (Table 1).In order to resolve this problem, we investigated the mass spectrometric behavior of compounds 1a-g and 2a.Compounds 1a-g and 2a were prepared from the indoles 3a-f and 1-alkyl-5-hydroxypyrrolidin-2-ones 4a and 4b according to our published procedure [1].The proposed schemes for electron impact fragmentation of indoles 1a-g and 2a are given in Figures 1-3. The numbering sequence of the fragment ions and the quantitative characteristics of this fragmentation are given in Tables 2 and 3.
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