Organogold(III) metallacyclic chemistry. Part 4. Synthesis, characterisation, and biological activity of gold(III)-thiosalicylate and -salicylate complexes |
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Authors: | Maarten B. Dinger William Henderson |
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Abstract: | The silver(I) oxide mediated reactions of the gold(III) dichloride complex [{C6H3(CH2uCl2] 2a with thiosalicylic or salicylic acid gives the respective complexes [{C6H3(CH2)-2}] 3a (X=S) or 6b (X=O), containing chelating thiosalicylate or salicylate dianion ligands. X-ray studies show that for the thiosalicylate system, the thiosalicylate sulfur atom is trans to the N,N-dimethylamino group, whereas in the structure of the salicylate complex, it is the carboxylate group that is trans to NMe2. Both complexes show puckered metallacycles in the solid state. Electrospray mass spectrometry (ESMS) shows strong [M+H]+ and [2M+H]+ ions for both the gold-thiosalicylate and -salicylate complexes, and these ions possess a high stability towards cone voltage-induced fragmentation. ESMS was also used to identify a minor impurity, the bis(cyclo-aurated) cationic complex [AMe2)-2-(OMe)-5}2]+ in the starting dihalide complex 2a and in the product 3a. This complex can be formed by reaction of Me4N[AuCl4] with 2 equivalents of the organomercury precursor [Hg{C6H3(CH2NMe2)-2-(OMe)-5}Cl]. The biological (antitumour, antimicrobial and antiviral) activities are also reported, and these reveal the complexes have moderate to high anti-tumour, antibacterial and antifungal activity. |
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Keywords: | Gold Thiosalicylate Salicylate Metallacycle Crystal structure Electrospray |
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