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Synthesis and characterization of tributyltin derivatives from 4‐oxo‐4‐(arylamino)butanoic acids and their in vitro biological activity against cervical cancer cell lines
Author(s) -
RojasOviedo Irma,
CamachoCamacho Carlos,
SánchezSánchez Luis,
Cárdenas Jorge,
LópezMuñoz Hugo,
EugenioRobledo Hugo,
Velázquez Israel,
Toscano Rubén Alfredo
Publication year - 2014
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3231
Subject(s) - chemistry , hela , aniline , stereochemistry , proton nmr , carbon 13 nmr , trifluoromethyl , thiazole , tributyltin , acetic anhydride , acylation , in vitro , organic chemistry , biochemistry , alkyl , catalysis
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 ( 1 H NMR, 13 C NMR, 119 Sn NMR and infrared), elemental analyses, mass spectrometry and X‐ray diffraction. All the tri‐ n ‐butyltin carboxylates exhibit 1 J ( 119/117 Sn– 13 C) 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 acylation 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 IC 50 value of 0.43 μM against the HeLa cell line. Copyright © 2014 John Wiley & Sons, Ltd.