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Resveratrol is a stilbenoid polyphenol with various antioxidant, antitumor, neuroprotective and cardioprotective properties, and due to low bioavailability, its biologically active derivatives are being developed. These analogs show significant antioxidant potential and inhibitory activity for the cholinesterase enzyme, which is proven by lower IC50 values compared to standard inhibitor galantamine. In this work, heteroaromatic derivatives of resveratrol were synthesized by the Wittig reaction, which served as starting compounds 1-5 for further photochemical transformations in batch and flow reactors. Photochemical transformations were carried out by direct illumination of the initial compounds at different wavelengths or in the presence of a porphyrin photocatalyst with four different LED lamps. In addition to the wavelength and the photocatalyst, the residence time and temperature also varied in the flow reactor. The results mainly show cyclization products as well as trans-cis isomerization, and computational study of the photoreactivity of the starting compound 1 determined the main paths of their obtaining. Comparing the productivity and selectivity of the reaction and yields of photoproducts, it was concluded that the flow reactor is a better choice compared to the batch reactor.
- Perinić, H
- University of Zagreb, Faculty of Chemical Engineering and Technology / Sveučilište u Zagrebu, Fakultet kemijskog inženjerstva i tehnologije
