title: Exploration of the SAR of anti-invasive chalcones: synthesis and biological evaluation of conformationally restricted analogues.
abstract: In order to get a clearer view on the active geometry of anti-invasive chalcones, we have prepared a number of isoxazoles and related substances as conformationally restrained mimics of 1,3-diarylpropenones, and also of (Z)-stilbenes. In vitro anti-invasive activity data for 3,5-isoxazoles and 4,5-isoxazoles, together with an in silico geometrical comparison, point towards an active conformation for chalcones more resembling their s-trans geometry than the s-cis counterpart.
authors: Research Group SynBioC, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors: Bart I
authors: BI
authors: Roman
authors: Tine De
authors: TD
authors: Ryck
authors: Laura
authors: L
authors: Dierickx
authors: Barbara W A
authors: BW
authors: Vanhoecke
authors: Alan R
authors: AR
authors: Katritzky
authors: Marc
authors: M
authors: Bracke
authors: Christian V
authors: CV
authors: Stevens
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy* / Q000473:pathology; D045744:Cell Line, Tumor; D047188:Chalcones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002642:Chick Embryo; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006321:Heart; D006801:Humans; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D008968:Molecular Conformation; D009361:Neoplasm Invasiveness / Q000473:pathology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D047188:Chalcones; D007555:Isoxazoles