Synthesis, structural characterization, and evaluation of biological activity of organotin(IV) complexes with 2-hydroxy-5-methoxybenzaldehyde-N(4)-methylthiosemicarbazone
| Autor: | Md. Abdus Salam, Irmawati Ramli, Mouayed A. Hussein, Md. Saiful Islam |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Stereochemistry Ligand Organic Chemistry chemistry.chemical_element Molar conductivity Crystal structure 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Inorganic Chemistry Metal Trigonal bipyramidal molecular geometry chemistry visual_art Materials Chemistry visual_art.visual_art_medium Moiety 2-Hydroxy-5-methoxybenzaldehyde Physical and Theoretical Chemistry Tin |
| Zdroj: | Journal of Organometallic Chemistry. 813:71-77 |
| ISSN: | 0022-328X |
| DOI: | 10.1016/j.jorganchem.2016.04.007 |
| Popis: | The reaction of organotin(IV) chloride(s) with 2-hydroxy-5-methoxybenzaldehyde-N(4)-methylthiosemicarbazone [H2dmmt, (1)] in the presence of potassium hydroxide yielded four new stable complexes, namely, [MeSnCl(dmmt)] (2), [BuSnCl(dmmt)] (3), [PhSnCl(dmmt)] (4), and [Ph2Sn(dmmt)] (5). The new compounds were characterized using CHN analyses, molar conductivity, UV–Vis, FT–IR, and 1H, 13C, and 119Sn NMR spectral studies. The molecular structures of H2dmmt (1) and its complex 5 were determined using X-ray crystallography. The X-ray crystal studies of complex 5 showed the trigonal bipyramidal geometry around the tin(IV) atom. The solid-state structure of complex 5 revealed that the dinegative tridentate ligand (1) is coordinated with the tin(IV) moiety via phenolic-O, azomethine-N, and thiolate-S atoms. The biological activities of the organotin(IV) complexes were investigated against a human colorectal (HCT 116) cell line and exhibited strong cytotoxic activities in the following order: 5 > 4 > 2 > 3 > H2dmmt. The organotin(IV) complexes (2–5) showed significant activity when compared with the standard drug, 5-fluorouracil (IC50 = 7.58 μM), and the parent ligand (IC50 = 7.19 μM). These results show that organotin(IV) complexes may be designed as new metal-based drugs in the future. |
| Databáze: | OpenAIRE |
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