This article outlines the synthesis and characterization of a structurally diverse range of mono- and 1,10-disubstituted ruthenocenyl complexes. Compounds were prepared through organic manipulation of ruthenocenefluorocarbonyl and carboxylic acid functional groups and via the Friedel-Crafts acylation of ruthenocene. A dimetalated acid anhydride of the formula [Ru(?5-C5H5)(?5-C5H4-CO)]2O was also prepared, and the X-ray structure of this molecule is reported. Complexes were evaluated for their antiproliferative properties against a range of tumorigenic cell lines and a control human fibroblast, with results indicating these organoruthenium metallocenes to possess moderate to weak cytotoxicity toward cancerous cells.