Aspirin is a common over‐the‐counter drug used to treat pain, fever, and inflammation. It is one of the most widely used medications in the world with an estimated 35,000 metric tons produced and consumed annually. Recent research has shown that the regular ingestion of aspirin reduces a person's risk of developing colon cancer and even promotes colorectal tumor regression. Moreover, aspirin has a demonstrated ability to inhibit the proliferation of colorectal cancer cells in vitro. Although the mechanism of action has not yet been unequivocally established, it is clear that the synthesis of novel aspirin analogs is of medicinal interest. In this study, a library of aspirin analogs of varying degrees of hydrophobicity and steric hindrance were synthesized using salicylic acid as the molecular scaffold and a variety of acyl chlorides. These aspirin analogs will be screened against an array of cancer cell lines and will also be evaluated as antibacterial agents to determine their medicinal activity. The medicinal testing of this library of aspirin analogs will help to establish new structure‐activity relationships. Support or Funding Information We would like to thank the Department of Natural Sciences at Lawrence Technological University and the Howard Hughes Medical Institute Inclusive Excellence grant for support and funding. This abstract is from the Experimental Biology 2018 Meeting. There is no full text article associated with this abstract published in The FASEB Journal .