Neighbouring-group participation as the key step in the reactivity of acyclic and cyclic salicyl-derived O,O-acetals with 5-fluorouracil. Antiproliferative activity, cell cycle dysregulation and apoptotic induction of new O,N-acetals against breast cancer cells

Antiproliferative Activity, Cell‐Cycle Dysregulation, and Cellular Differentiation: Salicyl‐ and Catechol‐Derived Acyclic 5‐Fluorouracil O,N‐Acetals against Breast Cancer Cells

“…Also shown are the biological activities of 8 a, 8 d, and 8 e [8] (entries 3-5), in order to establish the primary structure-activity studies related to the regioisomerism of the compounds.…”

“…[8] These molecules are characterized by the presence of ether-linked phenoxy and hydroxymethyl groups in an ortho relationship. The cytotoxic activity of molecules 8 a-e was assessed against the MCF-7 human breast cancer cell line.…”

Benzo-Fused Seven- and Six-Membered Derivatives Linked to Pyrimidines or Purines Induce Apoptosis of Human Metastatic Breast Cancer MCF-7 Cells In Vitro

“…In this way we have reported the synthesis and anticancer activities of compounds 3 (Campos et al, 1997), 4-6 (Saniger et al, 2003a), 7 , 8-9 (Saniger et al, 2003a) and trans-10 (Saniger et al, 2003b) (Figure 1). In all cases, the linkage between the 5-FU moiety and the seven-membered ring was carried out through its N-1 atom.…”

Apoptosis as a Therapeutic Target in Cancer and Cancer Stem Cells: Novel Strategies and Futures Perspectives

“…We have reported the synthesis and anticancer activities of compounds 1-5 [16] and trans-6 [17] (Figure 1). In all cases, the linkage between the 5-FU moiety and the seven-membered ring was carried out through its N-1 atom.…”

“…Moreover, these strategies overcome the adverse effects associated with cytotoxic drugs and increase their anti-cancer activity. Novel antitumour drugs have been synthesised such as 5-FU O,N-acetals and benzo-fused seven-membered O,N-acetal in which the 5-FU moiety was changed for the naturallyoccurring pyrimidine base uracil, which induced cell cycle-mediated apoptosis in breast and colon cancer cells [16,17,18,19]. The mechanism of action of these drugs was mainly centred on positive apoptosis regulatory pathway genes, and the repression of genes involved in carcinogenesis, proliferation and tumour invasion.…”