title: 2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents.
abstract: A variety of (Z)-[(2H-chromen-3-yl)methylene]azolidinones 6a-t bearing thiazolidine-2,4-dione, rhodanine or hydantoin scaffolds were designed and synthesized as potential anticancer agents. Inhibitory effect of synthesized compounds 6a-t on the viability of cancer and non-cancer cells was assessed using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) reduction assay. The SAR study revealed that the N-substitution of azolidinone moiety cannot improve the activity but S/NH replacement (thiazolidine-2,4-dione/hydantoin) and S/O alteration (rhodanine/thiazolidine-2,4-dione) enable us to modulate the growth inhibition activity against various cell lines. Moreover, 6-bromo and 2-methyl substituents on chromene ring had positive effects on growth inhibitory activity depending on the tumor cell lines. Among the synthesized compounds, hydantoin derivative 6o with a 6-bromo-2-methyl-2H-chromene substructure showed the best profile of cytotoxicity comparable to that of cisplatin as standard anticancer agent.
authors.affiliation: Chemistry Department, Zanjan University, P.O. Box 45195-313, Zanjan, Iran.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Azizmohammadi
authors.forename: Mehdi
authors.initials: M
authors.lastname: Khoobi
authors.forename: Ali
authors.initials: A
authors.lastname: Ramazani
authors.forename: Saeed
authors.initials: S
authors.lastname: Emami
authors.forename: Abdolhossein
authors.initials: A
authors.lastname: Zarrin
authors.forename: Omidreza
authors.initials: O
authors.lastname: Firuzi
authors.forename: Ramin
authors.initials: R
authors.lastname: Miri
authors.forename: Abbas
authors.initials: A
authors.lastname: Shafiee
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D006827:Hydantoins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D051379:Mice; D012236:Rhodanine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D001578:Benzopyrans; D006827:Hydantoins; D053778:Thiazolidines; D012236:Rhodanine