Di‐ and Triorganotin(IV) Esters of 3,4‐Methylenedioxyphenylpropenoic Acid: Synthesis, Spectroscopic Characterization and Biological Screening for Antimicrobial, Cytotoxic and Antitumor Activities

Abstract

Nine biologically significant organotin(IV) esters of 3,4-Methylenedioxyphenylpropenoic acid (L) were synthesized with the general formulae [R2SnL2], where R includes Me(1), Et(3), But(4), Oct(5), Ph(8), and [R3SnL], in which R is Me(2), Cy(6), Ph(7), and But(9). The acid and its compounds were characterized by basic analytical techniques comprising elemental analysis, FTIR and mass spectrometry in solid state and by Multinuclear (1H, 13C and 119Sn) NMR in solution form, which provides some important information about the different coordination behaviors of metal in both solid and solution. Methylenedioxy moiety in these compounds enhances the biological activity of these compounds. These compounds were screened for a range of biological activities. Antibacterial activities were determined against six pathogenic bacterial strains, three gram-positive and three gram-negative, the activities were measured in terms of inhibition zones (mm). Results demonstrate that diorganotin derivatives are more active than triorganotin derivatives and ligand acid. Antifungal activity was determined against six pathogenic fungal strains, cytotoxicity by the brine shrimp lethality assay, and antitumor activity by crown gall tumor inhibition (potato disc) assay. Results for antifungal activity, cytotoxicity, and antitumor activity of these compounds demonstrate that triorganotin derivatives are more active than diorganotin derivatives and ligand. Finally, the results were compared with similar reports in the literature.

Fluoro Substituted Monomeric and Uni-Dimensional Polymeric Organotin(IV) Esters of (E)-4-oxo-4-((3-trifluoromethyl)phenyl)amino)but-2-enoic acid; Synthesis, Characterization and Their In vitro Inhibitory Studies

“…In the 119 Sn NMR spectra of complexes 1-3, sharp peaks at 129.2, 135.6 and 115.3 ppm suggest four-coordinate tin as previously reported [27][28][29][30][31]. The signals for complexes 4-8 at -134.5, -158.4, 183.7, -179.2 and -150.5 ppm, imply penta-coordination around tin [32,33].…”

<i>In vitro</i> antimicrobial evaluation of pyrazolone derivatives

“…These plates were incubated at 37°C for 24 hours. The range of antimicrobial activity more than 30 mm shows potent activity, for 21-30 mm inhibition activity is strong activity, 16-20 mm is moderate activity, 10-15 mm is weak activity and below 10 mm is little or no activity (Jeon et al, 2014) or Inhibition zone more than 12 mm shows significant activity, for 10-12 mm inhibition activity is good, 7-9 mm is low, and below 7 mm is non-significant activity (Ahmad et al, 2008).…”

On the bioreactivity of triorganotin aminobenzoates. Investigation of trialkyl and triarylyltin(IV) esters of 3-amino and 4-aminobenzoic acids

“…Appreciable in vitro antitumor activity of triorganotin(IV) derivatives has also been reported [39,41,42]. Some of these compounds displayed high in vitro antitumor activity, which was comparable or even more potent than the clinically widely used cis-platin [40].…”

“…The antibacterial activities of triorganotin(IV) derivatives have been reported in several studies [39,40]. The prepared organotin complexes were tested against E. coli (XL-1) Gram-negative bacteria.…”