A new series of ferrocenyl selenoamides 7-11 (FcSeNH(CH(2))(n)CH(2)(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(CH(2))(2)OH] and 19 [PhSeNH(CH(2))(2)OH] 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 IC(50) 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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We report the synthesis of a new series of aryl-and heteroaryl (hydroxy)ethyl selenoamides, in a two-step, one-pot sequence based on the aminolysis/selenative demetalation of Fischer ethoxycarbene complexes, in good to excellent global yields, as small cytotoxic molecules. The molecular structure of a 2-thienyl based selenoamide was confirmed by single-crystal X-Ray diffraction analysis. In vitro analysis against different human cancer (HCT-15, U251 and PC-3) and human T-lymphocyte (MT2) cell lines revealed that the 2-thienyl based selenoamide can be considered a potent and selective compound against the human prostatic adenocarcinoma (PC-3) cell line with an IC50 value of 14.5 µM.