600708-84-7Relevant academic research and scientific papers
Medium benzene-fused oxacycles with the 5-fluorouracil moiety: Synthesis, antiproliferative activities and apoptosis induction in breast cancer cells
Saniger, Estrella,Campos, Joaquín M.,Entrena, Antonio,Marchal, Juan A.,Suárez, Inés,Aránega, Antonia,Choquesillo, Duane,Niclós, Juán,Gallo, Miguel á.,Espinosa, Antonio
, p. 5457 - 5467 (2007/10/03)
On the basis of the increase in lipophilicity, novel benzannelated six- and seven-membered derivatives have been synthesized, starting from 2-hydroxybenzyl alcohols, 2-hydroxybenzaldehydes, and catechol. The X-ray structure of (RS)-1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-5-fluorouracil (5) is presented and compared with its conformational analysis at the semiempirical (AM1) and ab initio (6-31G*) levels and NOE effects. A good agreement between both experimental and theoretical data was found showing a chair conformation for the 2,3-dihydro-5H-1,4-dioxepin ring and an axial orientation of the 5-FU moiety on the C3 position. Compounds 5 and (RS)-1-(7-methoxy-2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-5-fluorouracil (6) were found to be the most potent inhibitor of MCF-7 cells growth. (RS)-1-(2,3-Dihydrobenzoxepin-2-yl)-5-fluorouracil (8) induced apoptosis up to 57.33% of cell population after 24 h.
