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.

• Authors: Alejandro I Gutiérrez-Hernández, José G López-Cortés, M Carmen Ortega-Alfaro, M Teresa Ramírez-Apan, José de Jesús Cázares-Marinero, Rubén A Toscano
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 55 Issue 10 Pg. 4652-63 (May 24 2012) ISSN: 1520-4804 [Electronic] United States
• PMID: 22524555 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Amides
• Antineoplastic Agents
• Coordination Complexes
• Ferrous Compounds
• Metallocenes
• Organoselenium Compounds
• ferrocene

Topics

• Amides (chemical synthesis, chemistry, pharmacology)
• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Coordination Complexes (chemical synthesis, chemistry, pharmacology)
• Crystallography, X-Ray
• Drug Screening Assays, Antitumor
• Ferrous Compounds (chemical synthesis, chemistry, pharmacology)
• Humans
• Inhibitory Concentration 50
• Metallocenes
• Organoselenium Compounds (chemical synthesis, chemistry, pharmacology)
• Structure-Activity Relationship