Tributyltin(IV) Schiff base complexes with amino acid derivatives: synthesis, characterization and biological activity

• Published in: Applied organometallic chemistry 2016-04, Vol.30 (4), p.199-207
• Main Authors: Camacho-Camacho, Carlos, Rojas-Oviedo, Irma, Garza-Ortiz, Ariadna, Toscano, Rubén Alfredo, Sánchez-Sánchez, Luis, Cardenas, Jorge, López-Muñoz, Hugo
• Format: Article
• Language: English
• Subjects: amino acids; anti-proliferative activity; Biotechnology; Derivatives; In vitro testing; Nuclear magnetic resonance; Schiff bases; Strain; Structural analysis; Synthesis (chemistry); tributyltin(IV); X-ray diffraction
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.3417

The synthesis in one‐pot reactions and structural characterization of six new tri‐n‐butyltin(IV) derivatives of Schiff bases are reported. The compounds are derived from a condensation reaction between l‐alanine, l‐valine, l‐isoleucine, l‐methionine, l‐phenylalanine or l‐tryptophan and 3,5‐di‐tert‐butyl‐2‐hydroxybenzaldehyde. Characterization was completed using elemental analysis, infrared spectroscopy, mass spectrometry, one‐ and two‐dimensional solution NMR (1H, 13C and 119Sn) as well as solid‐state 119Sn NMR. In addition, the crystal structures of three of the compounds were confirmed using single‐crystal X‐ray diffraction. Although five‐coordinated and polymeric in the solid state, the tin compounds are four‐coordinated and monomeric in solution. The coordination environment around the triorganotin units comprises three carbon atoms and two oxygen atoms from two ligands in a trigonal bipyramidal geometry. The anti‐proliferative effect of these compounds on the cervical carcinoma cell lines HeLa, CaSki and ViBo was screened in vitro, the compounds showing cytotoxic activity against all three strains and null or low cytotoxic activity (necrotic) as well. Copyright © 2016 John Wiley & Sons, Ltd. The synthesis in one‐pot reactions and structural characterization of six new tri‐n‐butyltin(IV) derivatives of Schiff bases are reported. The anti‐proliferative effect of these compounds on HeLa, CaSki and ViBo cell lines was screened in vitro, the compounds showing cytotoxic activity against all three strains and null or low cytotoxic activity (necrotic) as well.