Q112372948
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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
- buňky K562 MeSH
- cytotoxiny chemická syntéza toxicita MeSH
- financování organizované MeSH
- lidé MeSH
- nádorové buněčné linie MeSH
- protinádorové látky chemická syntéza toxicita MeSH
- stereoizomerie MeSH
- uracil analogy a deriváty chemická syntéza toxicita MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- srovnávací studie MeSH
The preparation of 3-hydroxy-2-phenyl-4(1H)-quinolinones substituted in position 7 with a carboxyl group is described. The synthesis is based on the reaction of 2-aminoterephthalic acid with substituted alpha-bromoacetophenones and subsequent cyclization of the resulting bisphenacylesters in polyphosphoric acid. The reaction affords a mixture of substituted 3-hydroxy-2-phenyl-4(1H)-quinolinones 7-carboxylic acids as well as their phenacylesters. All quinolinones prepared (acids and phenacylesters) were tested for cytotoxic activity in vitro against five cancer cell lines and the results and a tentative structure-activity relationship are reported.
- MeSH
- biologická dostupnost MeSH
- chinoliny farmakologie chemická syntéza MeSH
- estery farmakologie chemická syntéza MeSH
- financování organizované MeSH
- indikátory a reagencie MeSH
- krystalografie rentgenová MeSH
- kyseliny karboxylové farmakologie chemická syntéza MeSH
- lidé MeSH
- magnetická rezonanční spektroskopie MeSH
- molekulární modely MeSH
- nádorové buněčné linie MeSH
- protinádorové látky farmakokinetika farmakologie chemická syntéza MeSH
- screeningové testy protinádorových léčiv MeSH
- tetrazoliové soli MeSH
- thiazoly MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
