Synthesis and antitumour evaluation of benzopsoralen analogues

• Author(s): Oliveira, Ana M. A. G. ; Campos, Ana M. F. Oliveira ; Rodrigues, Lígia M. ; Raposo, M. Manuela M. ; Machado, António E. H. ; Nascimento, Maria São José ; Nazareth, N. ; Pinto, Madalena
• Date: 2007
• Persistent ID: http://hdl.handle.net/1822/8646
• Origin: RepositóriUM - Universidade do Minho
• Subject(s): Psoralens; Xanthen-9-one; Carbazole; Antitumour; Coumarin
• Document Type: Article
• Language: English

Description

The synthesis of five new analogues of benzopsoralens, derived from xanthen-9-one and carbazole is described. The preparation of the hydroxylated precursors, their formylation and the formation of the pyranone ring, by the reaction between ortho-formylated heterocycles and diethyl malonate in EtOH, will be discussed. The inhibitory effect on the growth of human tumour cell lines (MCF-7, SF-268 and NCI-460) of the final products was evaluated and is discussed in terms of the 3D-geometry and electronic density distribution. The compounds showing significant biological activity in this study were those having angular structures.