Ferrocenylselenoamides: Synthesis, Characterization and Cytotoxic Properties

Abstract

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.

Selenoquinones Stabilized by Ruthenium(II) Arene Complexes: Synthesis, Structure, and Cytotoxicity

“…[6] These bond lengths are shorter than that reported for diselenocin with a CÀSe single bond of 1.924(8) [13] and are closer in value to the C=Se double bond of 1.857(9) reported for 2-selenoxoperhydro-1,3-selenazin-4-one. [14] The C=Se bond in 8 is slightly longer than that reported for seleno-acrylamide with a C=Se doublebond length of 1.837(4) , [15] selenobenzyl amide of length 1.830(2) , [16] and 4,4'-dimethoxy-selenobenzophenone with a C=Se bond length of 1.79 . [17] However, the reported bond length for a selenoaldehyde-tungsten complex is 1.854 , [18] which is comparable to that found in 8.…”

Organized Molecular Assemblies based on Ferrocenyl Derivatives

“…The new thioamide, with long alkyl side chain, was characterized by conventional spectroscopic techniques. The synthesis of ferrocenylselenoamide precursor, figure 6, was achieved using the same protocol previously described [9]. Hexadecylamine was used to add a 16-carbon aliphatic chain, figure 7.…”

“…For these ferrocene derivatives different elements as S, Se and Cr have been included, wherein a charge transfer donor group of ferrocene to these elements is possible by means of the conjugated bonds. For these LB films the photochemical behavior, semiconductor and their potential optical-electronic properties will be studied To obtain alkyl thioamides [8] and seleniumcarbonyl [9] compounds, ferrocenyl carbene complexes were used as precursors, figure 2, which were treated with NaBH4 to promote demetalation of ferrocenyl aminocarbene complexes with elemental sulfur or selenium to produce ferrocenylthioamide (1b) or ferrocenylselenoamide (1c) compounds. Finally, these nanostructures obtained from ferrocenyl derivatives were developed as Langmuir films (L) at the air-water interface.…”

Nanostructured LB Films Developed from Ferrocenylthioamide and Ferrocenylselenoamide Compounds

“…The new thioamide was characterized by conventional spectroscopic techniques. In general, the synthesis of ferrocenylselenoamide, figure 4, was achieved using the same protocol previuosly described [7]. Specifically, in this work we used hexadecylamine to add a 16-carbon aliphatic chain.…”

“…In a similar way, alkyl thioamides, new thiocarbonyl [6] and seleniumcarbonyl [7] moieties bonded to the ferrocene have been used as precursors of LB films. From ferrocenyl carbene complexes, previously synthesized [8], compounds were treated with NaBH 4 -promoted demetalation of ferrocenyl aminocarbene complexes with elemental sulfur or selenium as an alternative to obtain ferrocenylthioamide or ferrocenylselenoamide compounds.…”