Document Type
Article
Publication Date
5-1-2026
Abstract
Antimicrobial agents are one of the most important therapeutics used in the medical field. With the rising prevalence of antibiotic resistant bacteria, new strategies have been developed to combat them, with biofilm-inhibiting agents proving to be promising candidates. A class of molecules known as hemibastadins, first discovered from marine sponges, has garnered significant attention for their biofilm properties. This thesis investigates the synthesis of three derivatives of hemibastadin-1, which incorporate structural changes meant to improve their biofilm-inhibiting properties and biological safety. The selected modifications to the structure of hemibastadin-1 include the replacement of the brominated phenols with a safer polyphenolic system, as well as the use of a simpler triazole linker to replace the central oxime. The dimeric nature of these molecules has allowed for the development of a divergent and convergent synthetic pathway, preparing its two halves from the same starting material, then subsequently coupling the halves together. Implementation of this pathway has produced two hemibastadin derivatives, one symmetric utilizing the divergent route, and one asymmetric benzylamine-derived target, providing yields of 7% and 28% respectively. Ultimately, the preparation of these compounds will allow for the investigation of their antimicrobial and biofilm-inhibiting properties to better elucidate the structure-activity relationship of the hemibastadin-1 scaffold as a whole.
Recommended Citation
Daniel, James, "Design and Synthesis of Polyphenolic Hemibastadin Derivatives as Potential Biofilm Inhibitors" (2026). Longwood Senior Theses. 47.
https://digitalcommons.longwood.edu/senior_theses/47
