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Synthesis of furo[3,2-g]chromones under microwave irradiation and their antitumor activity evaluation
A series of furo[3,2-g]chromone derivatives were synthesized via the reaction of furochromone carbaldehyde 1 with amines 3a-d and thioglycolic acid to give thiazolidinones 4a-d. The later react with benzaldehyde/thiourea or hydroxylamine and DMF-DMA in glacial acetic acid to give thiazolopyrimidines 5a-d or thiazoloisoxazoles 6a-d, respectively. Also, the synthesis of alpha-aminophosphonates via the one-pot reaction of 1 and amines 3a,b were trapped by dialkylphosphites 7a-c afforded the corresponding alpha-aminophosphonates 8a-f. Applying hexaalkyltriamidophosphites 9a,b to 1 gives alkylidenephosphorane ylides 11a,b in an open structure form. In the present investigation, the in vitro inhibition capacity of compounds (4a, 4c, 5b, 5c, 6b-d, 8a-f, and 11a) was screened in three human cancer cell lines HCT-116, MCF-7, and HepG2. The anticancer activity results revealed that 8b and 8e had more potent cytotoxic inhibition activity against HCT-116 cell line; however, all the tested compounds had obviously less cytotoxic activity against MCF-7 cell line, while 5b, 5c, and 6d were potent against HepG2 cell line compared with that of doxorubicin.
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Reference£º
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem