Mononuclear homoleptic organotin(IV) dithiocarbamates: Syntheses, structures and antimicrobial activities

Four new macrocyclic dinuclear dibutyltin(IV) dithiocarbamate complexes of the type [Bu2Sn(dtc)]2, where dtc = hexane‐1,6‐diylbis(4‐fluorobenzyldithiocarbamate) anion (1), hexane‐1,6‐diylbis(4‐chlorobenzyldithiocarbamate) anion (2), hexane‐1,6‐diylbis(furfuryldithiocarbamate) anion (3) and hexane‐1,6‐diylbis(pyrrole‐2‐ylmethyldithiocarbamate) anion (4), have been prepared. The dithiocarbamate ligands efficiently self‐assemble with Bu2Sn(IV) to form bimetallic 26‐membered macrocycles. All the complexes have been characterized using elemental analysis, infrared and NMR (1H and 13C) spectroscopies and X‐ray crystallography. Single‐crystal X‐ray diffraction analysis of all the complexes confirms the formation of the dinuclear metallomacrocycles in which dithiocarbamate ligands are asymmetrically bound to the tin atoms. The coordination sphere around the tin atom in 1–4 can be described as a skew trapezoidal bipyramid. The dimensions of the cavity of the macrocycles of 1–4 are ca 8.0 × 9.0 Å2. Complexes 1–4 were evaluated for their in vitro anticancer activity against MCF‐7 and HL‐60 cells. Complexes 1 and 2 are more active against MCF‐7 and HL‐60. Thermal decomposition of 1 and 4 yielded tin sulfides. They were characterized using powder X‐ray diffraction (PXRD), high‐resolution transmission electron microscopy and UV diffuse reflectance and energy‐dispersive X‐ray spectroscopies. PXRD studies reveal that the as‐prepared tin sulfides are composed of orthorhombic phase of SnS.

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“…TGA studies of similar [Bu 2 Sn(dtc) 2 ] were carried out under air and nitrogen atmosphere. In these cases also, the final residue is SnS …”

Section: Resultsmentioning

confidence: 99%

Synthesis, spectra, crystal structures and anticancer studies of 26‐membered macrocyclic dibutyltin(IV) dithiocarbamate complexes: Single‐source precursors for tin sulfide nanoparticles

Selvaganapathi

Thirumaran

Ciattini³

2019

Applied Organom Chemis

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“…In the FT-IR spectra of these complexes, a strong thioureide ν(C-N) band was found in the region of 1489 cm -1 , 1485 cm -1 , respectively. 23 A sharp band assigned to the ѵ asym (C-S) stretching is observed at 1097 and 1093 cm -1 for (C2L1) and (C4L2), respectively. The v(Sn-S) bands (found in the far-infrared region) were observed around 411-459 cm −1 .…”

Section: Infrared Spectroscopymentioning

confidence: 95%

Synthesis, Characterization and Antibacterial Activity of Sn(II) and Sn(IV) Ions Complexes Containing N-Alkyl-N-Phenyl Dithiocarbamate Ligands

Abbas Ali,

Mihsen,

Guzar

2023

ChChT

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In the current study, ligands S2 donor atoms, sodium N-methyl-N-phenyldithiocarbamate [L1], and sodium N-ethyl-N-phenyldithiocarbamate [L2] are prepared from carbon disulfide with N-methyl aniline and N-ethyl aniline, respectively. Sn(II) and Sn(IV) ions complexes containing N-alkyl-N-Phenyl dithiocarbamateare prepared and characterized by CHNS elemental analysis, infrared spectroscopy (FT-IR), 1HNMR-spectroscopy, mass spectroscopy, UV-visible spectroscopy, magnetic susceptibility and conductivity measurements. The analytical and spectral data show that the stoichiometry for all complexes is 1 : 2 metal to ligand. The spectral data confirm good coordination of dithiocarbamate ligand with the metal through sulfur atoms of dithiocarbamate moiety. Molar conductivity of complexes are measured using DMF as a solvent and indicated that the complexes of Sn(II) are non-ionic whereas Sn(IV) complexes are ionic. The ligands L1 and L2 and their complexes are examined against Staphylococcus aureus bacteria and Escherichia coli bacteria.

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“…The triorganotin(IV) congeners displayed better antimicrobial potency towards the eight microbials tested (S. aureus, E. coli, B. subtilis, P. multocida, A. niger, A. flavus, R. solani, and A. alternata). Antimicrobial studies on Ph 3 Sn(L 71,77 ), Ph 2 Sn(L 71 )Cl, R 2 Sn(L 71 ) 2 with R = n-Bu and Ph, and Ph 2 Sn(L 77 ) 2 [105] indicated all compounds were effective against E. coli with Ph 3 Sn(L 71 ) being the most effective and Ph 3 Sn(L 77 ) being the least. This shows that in determining antibacterial activity both the tin and dithiocarbamate bound substituents must be taken into consideration.…”

Section: Main Group Element Dithiocarbamatesmentioning

confidence: 99%

Insights into the Antimicrobial Potential of Dithiocarbamate Anions and Metal-Based Species

2021

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Bacterial infection remains a worldwide problem that requires urgent addressing. Overuse and poor disposal of antibacterial agents abet the emergence of bacterial resistance mechanisms. There is a clear need for new approaches for the development of antibacterial therapeutics. Herein, the antibacterial potential of molecules based on dithiocarbamate anions, of general formula R(R’)NCS2(−), and metal salts of transition metals and main group elements, is summarized. Preclinical studies show a broad range of antibacterial potential, and these investigations are supported by appraisals of possible biological targets and mechanisms of action to guide chemical syntheses. This bibliographic review of the literature points to the exciting potential of dithiocarbamate-based therapeutics in the crucial battle against bacteria. Additionally, included in this overview, for the sake of completeness, is mention of the far fewer studies on the antifungal potential of dithiocarbamates and even less work conducted on antiparasitic behavior.

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Mononuclear homoleptic organotin(IV) dithiocarbamates: Syntheses, structures and antimicrobial activities

Cited by 12 publications

References 40 publications

Synthesis, spectra, crystal structures and anticancer studies of 26‐membered macrocyclic dibutyltin(IV) dithiocarbamate complexes: Single‐source precursors for tin sulfide nanoparticles

Synthesis, spectra, crystal structures and anticancer studies of 26‐membered macrocyclic dibutyltin(IV) dithiocarbamate complexes: Single‐source precursors for tin sulfide nanoparticles

Synthesis, Characterization and Antibacterial Activity of Sn(II) and Sn(IV) Ions Complexes Containing N-Alkyl-N-Phenyl Dithiocarbamate Ligands

Insights into the Antimicrobial Potential of Dithiocarbamate Anions and Metal-Based Species

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