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- Title
Synthesis and characterization of tributyltin derivatives from 4-oxo-4-(arylamino)butanoic acids and their in vitro.
- Authors
Rojas ‐ Oviedo, Irma; Camacho ‐ Camacho, Carlos; Sánchez ‐ Sánchez, Luis; Cárdenas, Jorge; López ‐ Muñoz, Hugo; Eugenio ‐ Robledo, Hugo; Velázquez, Israel; Toscano, Rubén Alfredo
- Abstract
Uterine (cervix and corpus) cancer is one of the major causes of mortality in women in Mexico. Organotin carboxylated derivatives have shown high cytotoxic activity against various cell lines of human origin. We describe the synthesis of three new tri- n-butyltin derivatives from 4-oxo-4-(arylamino)butanoic acids; their structures were confirmed using spectral data (1H NMR, 13C NMR, 119Sn NMR and infrared), elemental analyses, and X-ray diffraction. All the tri- n-butyltin carboxylates exhibit 1 J (119/117Sn-13C) coupling satellites in solution and lie in the range 357 to 339 Hz, suggesting a tetrahedral geometry around the tin atom. The polymeric structures of two of the derivatives and the monomeric structure of another were confirmed using X-ray crystallography. Using succinic anhydride as raw material, five N-substituted succinamic acid compounds were synthesized by the reaction with aniline, 4-nitroaniline, 4-nitro-3-(trifluoromethyl)aniline, 2-amino-5-nitrothiazole and 4-aminoantipyrine. From these compounds, five tin derivatives were prepared and their in vitro anti-proliferative effect on HeLa, CaSki and ViBo cell lines was screened. All of the compounds showed potency against all three strains and null or low cytotoxic activity (necrotic) as well. The most potent of our derivatives as an anti-proliferative agent against the three cell lines was tributylstannyl 4-oxo-4-[(3-trifluoromethyl-4-nitrophen-1-yl)amino]butanoate, exhibiting an IC50 value of 0.43 μM against the HeLa cell line. Copyright © 2014 John Wiley & Sons, Ltd.
- Subjects
UTERINE diseases; CERVICAL cancer; CELL lines; ORGANOTIN compounds; ORGANOMETALLIC compounds; ORGANIC synthesis; NUCLEAR magnetic resonance
- Publication
Applied Organometallic Chemistry, 2014, Vol 28, Issue 12, p884
- ISSN
0268-2605
- Publication type
Academic Journal
- DOI
10.1002/aoc.3231