Two aspirin (acetylsalicylic acid) derivatives were synthesized which have an aromatic or quinone substituent that forms an ester group at the former site of the carboxyl group of aspirin. An aromatic substiuent was formed utilizing martius yellow and a quinone moiety by utilizing the dye alizarin. The former derivative contains one aspirin molecule while the latter incorporates two aspirin molecules. Both aspirin derivatives showed measurable growth inhibition and/or aggregation of bacteria when tested against gram negative bacteria Escherichia coli. Bacterial inhibition was expressed at all solubilizing concentrations. The aqueous solubility of aspirin-alizarin derivative is determined to be 11.88 μg/mL while aspirin-martius yellow solubilizes to 31.3 μg/mL. Molecular modeling determined properties such as parachor, Log P, polar surface area, molecular volume, rotatable bonds, numbers of -OH & -NH, and molar refractivity. The aromatic and quinone substituents significantly increase the lipophilic characteristic of these constructs. Calculated molecular descriptors and observed antibacterial activity demonstrates druglikeness attributes for both derivatives. The aspirin component may be released into its active form upon esterase hydrolysis of the ester group linking acetylsalicylic acid to the fused ring moiety.