Synthesis of furo[3,2‐g]chromones under microwave irradiation and their antitumor activity evaluation

Abstract

AbstractA 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 α‐aminophosphonates via the one‐pot reaction of 1 and amines 3a,b were trapped by dialkylphosphites 7a‐c afforded the corresponding α‐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.