title: Asymmetrical 2,6-bis(benzylidene)cyclohexanones: Synthesis, cytotoxic activity and QSAR study.
abstract: In order to develop novel anti-cancer agents, a series of asymmetrical 2,6-bis (benzylidene)cyclohexanone derivatives containing nitrobenzylidene moiety were synthesized and their cytotoxic activity were determined in vitro against MDA-MB 231, MCF-7 and SK-N-MC cell lines using MTT assay. Among the tested compounds, the highest activity against MDA-MB 231 cells was achieved by 2-(3-bromo-5-methoxy-4-propoxybenzylidene)-6-(2-nitrobenzylidene)cyclohexanone (compound 5d). Whereas, compound 5j (the 3-nitro analog of compound 5d) was the most potent compound against MCF-7 and SK-N-MC cell lines. The results indicated that the cytotoxic activity profile against different tumor cells can be optimized by desired 4-alkoxy-3-bromo-5-methoxybenzylidene scaffold.
authors.affiliation: Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran.
authors.forename: Maryam
authors.initials: M
authors.lastname: Nakhjiri
authors.forename: Maliheh
authors.initials: M
authors.lastname: Safavi
authors.forename: Eskandar
authors.initials: E
authors.lastname: Alipour
authors.forename: Saeed
authors.initials: S
authors.lastname: Emami
authors.forename: Amir Farzin
authors.initials: AF
authors.lastname: Atash
authors.forename: Mona
authors.initials: M
authors.lastname: Jafari-Zavareh
authors.forename: Sussan K
authors.initials: SK
authors.lastname: Ardestani
authors.forename: Mehdi
authors.initials: M
authors.lastname: Khoshneviszadeh
authors.forename: Alireza
authors.initials: A
authors.lastname: Foroumadi
authors.forename: Abbas
authors.initials: A
authors.lastname: Shafiee
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D001597:Benzylidene Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy* / Q000473:pathology*; D049109:Cell Proliferation / Q000187:drug effects; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D015394:Molecular Structure; D009447:Neuroblastoma / Q000188:drug therapy* / Q000473:pathology*; D021281:Quantitative Structure-Activity Relationship; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: C573623:2-(3-bromo-5-methoxy-4-propoxybenzylidene)-6-(2-nitrobenzylidene)cyclohexanone; D000970:Antineoplastic Agents; D001597:Benzylidene Compounds; D003512:Cyclohexanones