title: Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648).
abstract: New fluorinated 2-aryl-benzothiazoles, -benzoxazoles, and -chromen-4-ones have been synthesized and their activity against MCF-7 and MDA 468 breast cancer cell lines compared with the potent antitumor benzothiazole 5. Analogues such as 9a, b and 12a, d yielded submicromolar GI50 values in both cell lines; however, none of the new compounds approached 5 in terms of antitumor potency. For 5, binding to the aryl hydrocarbon receptor appeared to be necessary but not sufficient for growth inhibition.
authors.affiliation: Welsh School of Pharmacy, Cardiff University, Redwood Building, King Edward VII Avenue, Cardiff, CF10 3NB, UK.
authors.forename: Stefania
authors.initials: S
authors.lastname: Aiello
authors.forename: Geoffrey
authors.initials: G
authors.lastname: Wells
authors.forename: Erica L
authors.initials: EL
authors.lastname: Stone
authors.forename: Hachemi
authors.initials: H
authors.lastname: Kadri
authors.forename: Rana
authors.initials: R
authors.lastname: Bazzi
authors.forename: David R
authors.initials: DR
authors.lastname: Bell
authors.forename: Malcolm F G
authors.initials: MF
authors.lastname: Stevens
authors.forename: Charles S
authors.initials: CS
authors.lastname: Matthews
authors.forename: Tracey D
authors.initials: TD
authors.lastname: Bradshaw
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Westwell
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D001943:Breast Neoplasms / Q000188:drug therapy; D002453:Cell Cycle / Q000187:drug effects; D045744:Cell Line, Tumor; D006801:Humans; D018336:Receptors, Aryl Hydrocarbon / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: C507816:2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole; D000970:Antineoplastic Agents; D001578:Benzopyrans; D052160:Benzothiazoles; D001583:Benzoxazoles; D018336:Receptors, Aryl Hydrocarbon