7505-91-1Relevant academic research and scientific papers
Synthesis of Aromatic Retinoids and Curcuminoids and Evaluation of their Antiproliferative, Antiradical, and Anti-inflammatory Activities
Morzycki, Jacek W.,Rárová, Lucie,Grúz, Ji?i,Sawczuk, Tomasz,Kie?czewska, Urszula,Siergiejczyk, Leszek,Wojtkielewicz, Agnieszka
, p. 339 - 350 (2016/08/19)
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.
Nucleophilic Attack on a Carbonyl Group Conjugated to a Chiral Centre: A Search For a Vinylogous Cram's Rule
Fleming, Ian,Kuehne, Hardy,Takai, Ken
, p. 725 - 728 (2007/10/02)
In a search for a vinylogous version of Cram's rule, 1,4-diphenylbut-2-ene-1,4-dione (5), 4-methoxy-1,4-diphenylbut-2-en-1-one (9), and hex-3-ene-2,5-dione (13) are found to be reduced with low or negligible diastereoselectivity.Similarly, the phenyl Grignard reagent showed no diastereoselectivity in its reaction with 4-methoxy-4-phenylbut-2-enal (12)
