Development of a Streamlined One-Pot Reaction Strategy for Phenoxathiin-Based Molecules in Prostate Cancer Research

Presenter: Ken Lei

Faculty Sponsor: Rachid Skouta

School: UMass Amherst

Research Area: Chemistry and Materials Science

Session: Poster Session 5, 3:15 PM - 4:00 PM, 165, D10

ABSTRACT

Prostate cancer (PC) remains a major health concern, particularly in metastatic stages where survival outcomes decline significantly. While patients with localized PC have approximately a 99% five-year survival rate, this decreases to about 30% when distant metastases are present. These disparities highlight the need for improved therapeutic strategies and more efficient synthetic approaches to support the development of novel small molecules for PC research. The efficiency of multistep synthetic routes often limits the rapid exploration of chemical scaffolds. This project focuses on optimizing a critical transformation in a multistep sequence through a one-pot, catalyzed strategy. Specifically, a 1,4-Michael addition followed by intramolecular cyclization is performed sequentially in a single reaction vessel, with the goal of improving reaction efficiency and operational simplicity. Various catalytic systems, including Lewis acids and bases, will be screened under controlled conditions to accelerate the transformation, while reaction progress will be monitored using thin-layer chromatography (TLC) and confirmed by NMR spectroscopy. By concentrating on reaction optimization and catalytic strategy, this work aims to establish a streamlined synthetic platform that can be applied broadly to phenoxathiin-based molecules. The resulting methodology will facilitate future analog synthesis and support downstream biological evaluation, while highlighting practical improvements in multistep reaction design relevant to prostate cancer–focused drug discovery.

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