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Ferrocenylselenoamides: Synthesis, Characterization and Cytotoxic Properties

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posted on 24.05.2012, 00:00 by Alejandro I. Gutiérrez-Hernández, José G. López-Cortés, M. Carmen Ortega-Alfaro, M. Teresa Ramírez-Apan, José de Jesús Cázares-Marinero, Rubén A. Toscano
A new series of ferrocenyl selenoamides 711 (FcSeNH­(CH2)nCH2(R)­OH, n = 1, 2, 3, R = H, Me, Ph) were prepared in good yields by selenative demetalation of Fischer aminocarbene complexes. The crystal structures of 7 [FcSeNH­(CH2)2OH] and 19 [PhSeNH­(CH2)2OH] reveal their capability to form intermolecular hydrogen bonding in solid state. Results of SRB assays show that these new selenium compounds have a good anticancer potency superior to tamoxifen and cisplatin, with IC50 values ranging from 4.5 to 13.32 μM against human breast cancer cell lines. A preliminary model to explain the structure–cytotoxic activity relation is proposed where different structural parameters such as the alkyl chain length, the presence of bulky groups in the same chain, the effect of hydroxyl group, and also the role of ferrocene moiety are included as being responsible for the cytotoxic response.

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