title: Synthesis and cytotoxic properties of novel (E)-3-benzylidene-7-methoxychroman-4-one derivatives.
abstract: OBJECTIVE
  There has been increscent interest in the field of cancer chemotherapy by discovery and development of novel agents with high efficacy, low toxicity, and minimum side effects. In order to find new anticancer agents, we replaced the pyrazolone part of well-known cytotoxic agent SJ-172550 with 7-methoxychroman-4-one. Thus, a novel series of 3-benzylidene-4-chromanones were synthesized and tested in vitro against human cancer cell lines.
  
  
  METHODS
  The title compounds were prepared by condensation of 7-methoxychroman-4-one with suitable aldehydes in appropriate alcohol in the presence of gaseous HCl. The antiproliferative activity of target compounds were evaluated against MDA-MB-231 (breast cancer), KB (nasopharyngeal epidermoid carcinoma) and SK-N-MC (human neuroblastoma) cell lines using MTT assay.
  
  
  RESULTS
  Although the direct analog of SJ-172550 (compound 5d) did not show any cytotoxic activity against tested cell lines, but 2-(2-chloro-6-methoxyphenoxy)acetic acid methyl ester analog 5c showed some activity against MDA-MB-231 and SK-N-MC cells. Further modification of compound 5c resulted in the 3-chloro-4,5-dimethoxybenzylidene derivative 5b which demonstrated better cytotoxic profile against all tested cell lines (IC50 values = 7.56-25.04 μg/ml).
  
  
  CONCLUSIONS
  The results demonstrated that the cytotoxic activity of compound 5b against MDA-MB-231 and SK-N-MC cells is more than etoposide. Therefore, compound 5b prototype could be considered as novel cytotoxic agent for further developing new anticancer chemotherapeutics.
authors.forename: Saeedeh
authors.initials: S
authors.lastname: Noushini
authors.forename: Eskandar
authors.initials: E
authors.lastname: Alipour
authors.forename: Saeed
authors.initials: S
authors.lastname: Emami
authors.forename: Maliheh
authors.initials: M
authors.lastname: Safavi
authors.forename: Sussan Kabudanian
authors.initials: SK
authors.lastname: Ardestani
authors.forename: Ahmad Reza
authors.initials: AR
authors.lastname: Gohari
authors.forename: Abbas
authors.initials: A
authors.lastname: Shafiee
authors.forename: Alireza
authors.initials: A
authors.lastname: Foroumadi
mesh_terms: D000085:Acetates / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D007529:Isoflavones / Q000138:chemical synthesis* / Q000494:pharmacology*; D011720:Pyrazoles / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000085:Acetates; D000970:Antineoplastic Agents; D007529:Isoflavones; D011720:Pyrazoles; C549331:SJ 172550; C046923:methyl acetate