title: Synthesis of Aromatic Retinoids and Curcuminoids and Evaluation of their Antiproliferative, Antiradical, and Anti-inflammatory Activities.
abstract: Natural retinoids and curcuminoids are known for their broad spectrum of biological properties, such as antioxidant, anti-inflammatory, antitumor, and so forth. In this work, a convenient synthesis of aromatic retinoids and curcuminoids from vinyl or allyl ketones, and the corresponding alcohols, using olefin metathesis as a key reaction, was elaborated. The best yields and diastereoselectivities were obtained from allylic or homoallylic alcohols by employing the two-step cross-metathesis/oxidation procedure. The synthesized analogues were tested for their antiproliferative activity on human cancer cell lines of various origin (leukemia CEM, adenocarcinoma MCF7, cervical carcinoma HeLa) as well as for their antioxidant and anti-inflammatory activity in vitro. All examined derivatives exhibited strong anti-inflammatory activity in vitro without affecting cell viability. They also showed strong cytotoxicity against leukemia cell line CEM, except for 18 and 35. The antioxidant activity of the tested compounds was rather weak.
authors.affiliation: Institute of Chemistry University of Białystok ul. K. Ciołkowskiego 1K 15-245 Białystok Poland.
authors.forename: Jacek W
authors.initials: JW
authors.lastname: Morzycki
authors.affiliation: Department of Chemical Biology and Genetics Centre of the Region Haná for Biotechnological and Agricultural Research Palacký University Šlechtitelů 27 783 71 Olomouc Czech Republic.
authors.forename: Lucie
authors.initials: L
authors.lastname: Rárová
authors.affiliation: Department of Chemical Biology and Genetics Centre of the Region Haná for Biotechnological and Agricultural Research Palacký University Šlechtitelů 27 783 71 Olomouc Czech Republic.
authors.forename: Jiři
authors.initials: J
authors.lastname: Grúz
authors.affiliation: Institute of Chemistry University of Białystok ul. K. Ciołkowskiego 1K 15-245 Białystok Poland.
authors.forename: Tomasz
authors.initials: T
authors.lastname: Sawczuk
authors.affiliation: Institute of Chemistry University of Białystok ul. K. Ciołkowskiego 1K 15-245 Białystok Poland.
authors.forename: Urszula
authors.initials: U
authors.lastname: Kiełczewska
authors.affiliation: Institute of Chemistry University of Białystok ul. K. Ciołkowskiego 1K 15-245 Białystok Poland.
authors.forename: Leszek
authors.initials: L
authors.lastname: Siergiejczyk
authors.affiliation: Institute of Chemistry University of Białystok ul. K. Ciołkowskiego 1K 15-245 Białystok Poland.
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Wojtkielewicz
keywords: anti-inflammatory activity; antitumor agents; curcuminoids; metathesis; retinoids