We performed a structure-activity relationship (SAR) study of novel derivatives of aspirin (ASA) which show strong anticancer activity in vitro and in vivo. We synthesized a series of ASA-based benzyl esters (ABEs) and evaluated their inhibitory activity against human colon (HT-29 and SW480) and pancreatic cancer cell lines (BxPC-3 and MIA PaCa-2). The ABEs that we studied largely comprise organic benzyl esters bearing an ASA or acyloxy group (X) at the meta or para position of the benzyl ring and one of four different leaving groups. The nature of the salicyloyl/acyloxy function, the leaving group, and the additional substituents affecting the electron density of the benzyl ring, all were influential determinants of the cancer cell growth inhibitory activity of each ABE. Positional isomerism also played a significant role in this effect. Our SAR study provides an insight into the biological properties of this novel class of compounds and underscores their potential as anticancer agents.

Citation Format: {Authors}. {Abstract title} [abstract]. In: Proceedings of the 101st Annual Meeting of the American Association for Cancer Research; 2010 Apr 17-21; Washington, DC. Philadelphia (PA): AACR; Cancer Res 2010;70(8 Suppl):Abstract nr 745.