Synthesis, characterization, and biological evaluation of eight new organotin(IV) complexes derived from (1R, 2S) ephedrinedithiocarbamate ligand

[Display omitted] •Synthesis of new organotin (IV) complexes derived from (1R, 2S) ephedrinedithiocarbamate ligand.•Antibacterial activity of organotin(IV) ephedrinedithiocarbamate.•Structure of organotin(IV) ephedrinedithiocarbamate is in an anisobidentate coordination. The synthesis of eight new o...

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Published in:Inorganica Chimica Acta 2022-05, Vol.534, p.120810, Article 120810
Main Authors: Ariza-Roldán, Aldo, López-Cardoso, Marcela, Tlahuext, Hugo, Vargas-Pineda, Gabriela, Román-Bravo, Perla, Acevedo-Quiroz, Macdiel, Alvarez-Fitz, Patricia, Cea-Olivares, Raymundo
Format: Article
Language:English
Subjects:
Chemical analysis
Complex biological activity
Coordination numbers
Crystals
Dichlorides
Ephedrine
Ephedrine dithiocarbamate
Infrared analysis
Infrared spectra
Infrared spectroscopy
Ligands
NMR spectroscopy
Organotin dithiocarbamate
Single crystals
Sodium
Spectrum analysis
Synthesis
X-ray single-crystal
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Summary:[Display omitted] •Synthesis of new organotin (IV) complexes derived from (1R, 2S) ephedrinedithiocarbamate ligand.•Antibacterial activity of organotin(IV) ephedrinedithiocarbamate.•Structure of organotin(IV) ephedrinedithiocarbamate is in an anisobidentate coordination. The synthesis of eight new organotin derivatives containing ephedrine-substituted dithiocarbamate ligands [R3Sn(ephedtc)] 2–5. 2: R = Me; 3: R = Bu; 4: R = Cy; 5: R = Ph and [R2Sn(ephdtc)2] 6–9. 6: R = Me; 7: R = Bu; 8: R = t-Bu; 9: R = Ph is reported. The complexes were obtained from sodium ephedrinedithiocarbamate [Na(ephedtc)] 1 and the corresponding tri-organotin(IV) chlorides, R3SnCl 2–5 or di-organotin(IV) dichlorides, R2SnCl26–9. They were characterized by elemental analysis, IR, and NMR spectroscopy (1H, 13C, and 119Sn). The infrared spectra (solid-state) suggest that the Sn(IV) is coordinated to the ligand ephedtc, through the two sulfur atoms in an anisobidentate coordination mode. In solution, the 119Sn NMR indicates the coordination numbers: tetracoordinated for 2–4, pentacoordinate for 5, and hexacoordinated for 6–9. The single-crystal X-ray diffraction analysis of 4 reveals an anisobidentate coordination mode with a trigonal bipyramid distorted geometry around the Sn(IV). All compounds except 2, show inhibition in at least one bacterial strain, and 7 and 9 have the best antibacterial activity, mainly in the clinically isolated strains.
ISSN:0020-1693
1873-3255
DOI:10.1016/j.ica.2022.120810