Study On Synthesis Of Chroman And Chromanone Glycosides

The chroman derivatives and chromanone derivatives with the scaffold of benzopyran are a series of natural products which are widespread in the natural world. Some chroman derivatives and chromanone derivatives exhibit a series of biological activities such as anti-tumor activity. In this paper, the classification, mechanism of anti-tumor drugs were summarized, and the anti-tumor activity of chroman derivatives and chromanone derivatives were surveyed.In order to discover some new anti-tumor agents with chroman moiety and chromanone moiety, a series of glycosides with chroman moiety and chromanone moiety were designed and synthesized.Based on our previous work, four intermediates, i.e.6-hydroxychroman,7-hydroxychroman, 6-hydroxyl-4-chromanone and 7-hydroxyl-4-chromanone were synthesized from resorcinol, 2’,5’-dihydroxyacetophenone, ethyl orthoformate were used as raw material. Glycosylations between the above four intermediates as glycosyl acceptors, and 1-O-acetyl sugars or 1-bromo-O-acetyl sugars as glycosyl donors in the presence of boron trifluoride ethyl etherate or ammoinium tetrabutyl bromide were performed. Following glycosylation, deacetylation in the presence of sodium methanolate resulted in 11 glycosides with chroman moiety and chromanone moiety. All target compounds were characterized by 1H-NMR, ESI-MS and IR, and were not reported in the literature according to the search results by SciFinder.The biological evaluation of all target compounds is under studying.