Synthesis and anticancer activity studies of novel 1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)uracil and (6′-substituted)-7- or 9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-7H- or 9H-purines

On the basis of a molecular variation on an isosteric replacement (F -> H) from the prototype (RS)-1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-5-fluorouracil, the derivative (RS)-1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)uracil 4 was prepared. Later on, the pyrimidine base was substituted by the purine moiety with the objective of increasing both the lipophilicity and the structural diversity of the target molecules. The 6'-halogen substituent of the (RS)-9- or 7-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-9H- or 7H-purines shows an interesting reactivity, which is presented and discussed. The anticarcinogenic potential of the target molecules is reported against the MCF-7 cancer cell line. (c) 2006 Elsevier Ltd. All rights reserved.