In solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the solid-phase synthesis of pyrrolidine-2,4-diones, which represent the core structure of several natural products, including tetramic acid. Base-triggered condensation of pyrrolidine-2,4-diones yielded 4-hydroxy-1,1',2',5-tetrahydro-2H,5'H-[3,3'-bipyrrole]-2,5'-diones.
- MeSH
- alkoholy * chemická syntéza chemie MeSH
- aminy chemie MeSH
- ketony * chemická syntéza chemie MeSH
- Publikační typ
- časopisecké články MeSH
The preparation of various 5-[alkoxy-(4-nitro-phenyl)-methyl]-uracils with alkyl chain lengths C(1)-C(12) is described. The synthesis is based on the preparation of 5-[chloro-(4-nitro-phenyl)-methyl]-uracil and subsequent substitution of chlorine with appropriate alcohols. The resulting ethers were tested for their cytotoxic activity in vitro against five cancer cell lines. The compounds were less active in lung resistance protein expressing cell lines, suggesting the involvement of this multidrug resistant protein in control of the biological activity. Cytotoxic substances induced rapid inhibition of DNA and modulation of RNA synthesis followed by induction of apoptosis. The data indicate that the biological activity of 5-[alkoxy-(4-nitro-phenyl)-methyl]-uracils depends on the alkyl chain length.
- MeSH
- alkoholy chemická syntéza toxicita MeSH
- antitumorózní látky chemická syntéza toxicita MeSH
- buňky K562 MeSH
- cytotoxiny chemická syntéza toxicita MeSH
- financování organizované MeSH
- lidé MeSH
- nádorové buněčné linie MeSH
- stereoizomerie MeSH
- uracil analogy a deriváty chemická syntéza toxicita MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- srovnávací studie MeSH
