Synthesis and characterization of cobalt and nickel chelates of 5-dimethylaminomethyl-2-thiouracil and their evaluation as antimicrobial and anticancer agents.
A new antimetabolite of adenine, viz. 5-dimethylaminomethyl-2-thiouracil, was synthesized using the Mannich reaction. Owing to the biological importance of metalloelements in many biological processes, especially metabolic processes, cobalt(II) and nickel(II) complexes were also synthesized and examined for their antimicrobial and anticancer activities. These new compounds were characterized structurally by various techniques ranging from micro-elemental analyses to spectral analyses. Cobalt(II) complexes were found to be four coordinate, among which the bromo, iodo, and nitrato complexes were polymeric. The nickel(II) isothiocyanato complex exhibited four-coordinate geometry and the remaining nickel(II) complexes were six coordinate. Thermodynamic and kinetic parameters evaluated based on TG/DSC suggested that the initial stage of thermal decomposition follows a diffusion-controlled mechanism and the final stage a chemically controlled mechanism. Antibacterial, antifungal, and antitumor studies undertaken for the above compounds indicated structure-activity relationships. These metalloderivatives were more active than the parent compound. The order of activity was influenced by the chelate geometry and thermal stability. Activity increased with a decrease in coordination number and increase in thermal lability.
Kamalakannan
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P
Department of Chemistry, Regional Engineering College, Tiruchirappalli 620 015, Tamilnadu, India,
Venkappayya
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D
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002614:Chelating Agents; D003035:Cobalt / Q000494:pharmacology; D004563:Electrochemistry; D004926:Escherichia coli / Q000187:drug effects; D007941:Leukemia P388 / Q000188:drug therapy; D008223:Lymphoma; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008811:Mice, Inbred DBA; D009532:Nickel / Q000494:pharmacology; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017550:Spectroscopy, Fourier Transform Infrared; D013211:Staphylococcus aureus / Q000187:drug effects; D013889:Thiouracil / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C460299:5-dimethylaminomethyl-2-thiouracil; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D002614:Chelating Agents; D009942:Organometallic Compounds; D003035:Cobalt; D013889:Thiouracil; D009532:Nickel