Synthesis, Characterization, Biocide and Toxicological Activities of Di-n-butyl- and Diphenyl-tin^IV-Salicyliden-β-Amino Alcohol Derivatives

Abstract

The one pot reaction of salicylaldehyde 1, beta-amino alcohols 2a-2c, and di-n-butyltin(IV) oxide 3a or diphenyltin(IV) oxide 3b produced five diorganotin(IV) compounds, 4a-4c, 5a, and 5c, in good yields. All compounds were characterized by IR, (1)H, (13)C, and (119)Sn NMR spectroscopy, and elemental analysis; furthermore, compounds 4b, 4c, 5a, and 5c were characterized by X-ray diffraction analysis. After the structural characterization, all of the compounds were tested in vitro against Bacillus subtilis (Gram-positive, strain ATCC 6633), Escherichia coli (Gram-negative, strain DH5alpha), Pseudomonas aeruginosa (Gram-negative, strain BH3), Desulfovibrio longus (strain DSM 6739), and Desulfomicrobium aspheronum (strain DSM 5918) to assess their antimicrobial activity. Compounds 4 and 5 demonstrated a wide range of bactericidal activities against the tested aerobic (one Gram-positive and two Gram-negative subtypes) and anaerobic bacteria (two sulfate-reducing bacteria, SRB). Compound 5 had better bactericidal performances than compound 4. For all of the compounds, the acute toxicity was measured using luminescent bacteria toxicity (LBT-Microtox) tests to track their further environmental impact. According to these results and in order to fulfill environmental regulations, the toxicity of the compounds studied herein can be modulated through the proper selection of the disubstituted tin(IV) moiety.

Synthesis, characterization, and in vitro antimicrobial activities of organotin(IV) complexes of Schiff bases with ONO‐type donor atoms

“…The 1 H NMR spectra of all the ligands display a single signal for the azomethine proton (H-7) at 9.00-9.05 ppm, in a good agreement with the reported data for similar structures [15,19,20,33]. The H-7 NMR signal of tin(IV) complexes downshift to the range 8.61-8.74 ppm, reflecting the more electropositive nature of the tin atom relative to hydrogen.…”

Synthesis and characterization of di-phenyl-tinIV-salicyliden-ortho-aminophenols: Analysis of in vitro antitumor/antioxidant activities and molecular structures

“…In particular, the toxicity in mammals has been extensively proven for di-and tri-n-butyl-tin IV compounds and just recently has been underlined that di-aryl-tins IV could be even less toxic than most tin moieties since minimum damage at the lipidic membrane occurred in erythrocytes [11]. Because very new evidences support the study of such derivatives both the di-and tri-phenyl-tin IV 's have been studied pretty less [34,35].…”

“…All of them are important hypotheses from basic and applied research viewpoints. In this line we set together molecular motifs which resulted important for biological studies and close to our research lines: (i) Schiff bases and their tin and organotin derivatives [38][39][40][41][42][43] have been tested in vitro in antitumor assays showing moderate-good activity; (ii) di-n-butyl-tin IV compounds with ortho-aminophenols presented better antitumor activities and less damage in normal cells when compared against cis-platin [44]; (iii) the statements that di-phenyl-tin IV derivatives could result pretty less toxic than other di-organo-tin IV derivatives due to their interaction towards the cell membrane [10][11][12]37]; (iv) the advantage that in our group there have been prepared three different series of monomeric di-phenyl-tin IV derivatives [34,45,46] with Schiff bases (instead of mono-, di-or polymeric forms when di-n-butyl-tin IV fragments are employed) [34,46,47]; (v) it has been reported one di-phenyl-tin IV compound possessing this set of molecular variables [48], 3 X-ray structures were found in the CCDC, two were reported by our work group [49], and none of them has been biologically tested. Therefore, it merits studying a family of compounds based in this lead di-phenyl-tin IV derivative with single chemical modifications now with the premise of evaluating not one but two biological activities to determine specificity.…”

“…Concomitantly, it has been proposed that the cell oxidative stress has been directly related towards cancer disease [50][51][52] thus counterpart activities are going to be measured. To prepare the desired tin compounds we applied a one pot reaction of salicylaldehyde, ortho-aminophenols, and di-phenyl-tin IV oxide giving seven di-phenyl-tin IV compounds in a similar fashion as that previously reported [34,46,47]. The molecular variations through different substitutions were centered in the ortho-aminophenol moiety to track the resulting responses in biological activities and hence define relationships.…”

A Bis(di‐n‐butyltin)–Quinone Derivative as a Simultaneous Chemo‐ and Bioactive Corrosion Inhibitor

“…[6] The corrosion inhibition activity of these compounds provided efficiencies in the range 61-87 % at concentrations of 500 ppm, and it was proposed that the concave π-electrondelocalized nanocap morphology of these compounds may induce an effective adsorption on the steel surface. In addition, tin compounds are capable of acting as biocides and have relatively low toxicities, [7] thus making them an attractive object of research for the development of chemicals having combined anticorrosive and antibacterial properties. This is because anaerobic bacteria are able to catalyze the corrosion processes in oil plants and pipelines.…”