2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents
| Autor: | Ali Ramazani, Mohammad Azizmohammadi, Abbas Shafiee, Ramin Miri, Abdolhossein Zarrin, Saeed Emami, Mehdi Khoobi, Omidreza Firuzi |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
Rhodanine
Cell Survival Stereochemistry Hydantoin Antineoplastic Agents Inhibitory Concentration 50 Mice Structure-Activity Relationship chemistry.chemical_compound Bromide Cell Line Tumor Drug Discovery Animals Humans Structure–activity relationship Moiety Benzopyrans Methylene Cytotoxicity Pharmacology Hydantoins Organic Chemistry General Medicine chemistry Thiazolidines Growth inhibition |
| Zdroj: | European Journal of Medicinal Chemistry. 59:15-22 |
| ISSN: | 0223-5234 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect