Synthesis and cytotoxic activity of various 5-[alkoxy-(4-nitro-phenyl)-methyl]-uracils in their racemic form
Language English Country Great Britain, England Media print-electronic
Document type Comparative Study, Journal Article, Research Support, Non-U.S. Gov't
PubMed
17935983
DOI
10.1016/j.bmcl.2007.09.022
PII: S0960-894X(07)01059-1
Knihovny.cz E-resources
- MeSH
- Alcohols chemical synthesis toxicity MeSH
- K562 Cells MeSH
- Cytotoxins chemical synthesis toxicity MeSH
- Humans MeSH
- Cell Line, Tumor MeSH
- Antineoplastic Agents chemical synthesis toxicity MeSH
- Stereoisomerism MeSH
- Uracil analogs & derivatives chemical synthesis toxicity MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Comparative Study MeSH
- Names of Substances
- Alcohols MeSH
- alkoxyl radical MeSH Browser
- Cytotoxins MeSH
- Antineoplastic Agents MeSH
- Uracil 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.
References provided by Crossref.org
Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues
