Molecules based on the 5-arylthio-5H-chromenopyridine structure have been studied for a variety of medicinal applications, including liver fibrosis. We have recently found that the C-S linkage can be cleaved with Pt(II) and Au(I), something that was not proviously recrognized. In this current work, we examine the structure, properties, and reactivity of 5-arylthio-5Hchromenopyridines using spectroscopy, crystallography, reactivity, and density functional theory calculations. We report the crystal structures of 5-arylthio-5H-chromenopyridines, as well as their DFT-calculated structures and electronic structures. The DFT calculations help to explain the electronic properties of these complexes, such as the observation that “soft” metals cleave the C–S bond. We find that the arylthio group is a good leaving group on these molecules due to the stability of the carbocation that is formed, and can be removed via reduction with NaBH4. Methoxy-substituted chromenopyridines were found to be viable at inhibiting liver fibrosis. These results will help inform the biological studies with these complexes to determine method of action and enhance development of new drug molecules with increased stability and activity based on the 5H-chromenopyridine scaffold.

Understanding the structure and reactivity of the C-S linkage in biologically active 5-arylthio-5Hchromenopyridines

255th National Meeting (2018)

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