The N(4)-methylthiosemicarbazone derivatives H2DDMT (1) and H2DMMT (2) have been prepared from the reaction of 4-methylthiosemicarbazide with 2,3-dihydroxybenzaldehyde and 2-hydroxy-5-methylbenzaldehyde, respectively. Six new organotin(IV) complexes, [MeSnCl(DDMT)] (3), [BuSnCl(DDMT)] (4), [PhSnCl(DDMT)] (5), [MeSnCl(DMMT)] (6), [BuSnCl(DMMT)] (7), and [PhSnCl(DMMT)] (8) have been synthesized by direct reaction of corresponding organotin(IV) chloride(s) with these ligands. The ligands and their compounds have been characterized by elemental analysis, molar conductivity, UV–Vis, FT-IR, and NMR (1H, 13C, and 119Sn) spectroscopy. The molecular structures of 1 and 2 were determined by X-ray crystallography. Spectroscopic data suggested that the ligands were coordinated to tin(IV) as dinegative tridentate via phenoxide-O, azomethine-N, and thiolate-S atoms. The crystal structures revealed that the ligands exist in thione form in the solid state. In vitro cytotoxicity assays were carried out for all the...

New organotin(IV) complexes with N(4)-methylthiosemicarbazone derivatives prepared from 2,3-dihydroxybenzaldehyde and 2-hydroxy-5-methylbenzaldehyde: synthesis, characterization, and cytotoxic activity

Abstract Five new triphenyltin complexes of N-(5-bromosalicylidene)-α-amino acids, 5-Br-2-HOC6H3C(H)=NCH(R)COOSnPh3 (where R=H, 1; Me, 2; i-Pr, 3; i-Bu, 4; s-Bu, 5), were synthesized by one-step reactions of triphenyltin hydroxide, 5-bromosalicylaldehyde, and α-amino acid in 1:1:1 molar ratios and characterized by elemental analysis, IR, and NMR (1H, 13C, and 119Sn) spectra. The crystal structures of 5-Br-2-HOC6H3C(H)=NCH(i-Pr)COOSnPh3 (3) and 5-Br-2-HOC6H3C(H)=NCH(s-Bu)COOSnPh3 (5) were determined and showed that the tin atom is five-coordinated and adopts a polymeric trans-O2SnC3 trigonal bipyramidal configuration with the axial positions occupied by a carboxylate oxygen from the ligand and the phenolic oxygen of the ligand in an adjacent complex. Bioassay results indicated that these compounds have stronger cytotoxic activity against three human tumor cell lines, HeLa, CoLo205 and MCF-7, than that of cis-platin used clinically.

Synthesis, characterization, and cytotoxic activity of triphenyltin complexes of N-(5-bromosalicylidene)-α-amino acids

Two new bis(tricyclohexyltin)benzenedioxyacetates, 1,x-C6H4[OCH2CO2Sn(c-C6H11)3]2 (1: x = 3; 2: x = 4), have been synthesized and characterized by means of elemental analysis, infrared and NMR (1H, 13C and 119Sn) spectra and single-crystal X-ray diffraction. Compound 1⋅H2O⋅CH3OH is a binuclear tin complex containing a four-coordinated tin and a five-coordinated tin and linked by an R33(16) hydrogen bond into a one-dimensional supramolecular chain. Compound 2 is a two-dimensional coordination polymer which is formed as a result of anisobidentate bridging coordination action of the two carboxylate units of the ligand. Interestingly the two-dimensional coordination polymer contains 34-membered macrocycles each of which is comprised of four tricyclohexyltin units. Both compounds have potent in vitro cytotoxic activity against three human tumor cell lines: HeLa, MCF-7 and CoLo 205. Copyright © 2015 John Wiley & Sons, Ltd.

Synthesis, crystal structure and cytotoxic activity of tricyclohexyltin complexes of benzenedioxyacetic acids: Tricyclohexyltin complexes of benzenedioxyacetic acids

Cancer cases are alarmingly increasing worldwide, and newer chemotherapeutic agents are needed. Recent analogs of cisplatin (carboplatin, lobaplatin, nedaplatin and oxaliplatin) and their marketing as advanced chemotherapeutic drugs have furthered the interest in metal-based anti-cancer drugs. In the current study, two new polymeric organotin(IV) carboxylate complexes (1 and 2) have been synthesized and characterized. Spectroscopic studies showed that coordination took place via carboxylates. Furthermore, X-ray crystallographic study on 1 indicated that it possesses a monomeric structure and exists in polymeric formation due to additional Sn–N coordination, assigning seven coordinations to each metal ion. Both the complexes were tested against three cancerous (human colon cancer, HCT 116; breast cancer, MCF-7; and leukemia, K562) and one non-cancerous (3T3-L1) cell lines. Complex 1 showed exceptional cytotoxicity against cancerous cell lines (IC50 = 1.0 μM for HCT 116; 258.7 nM for MCF-7; and 46.7 nM K562...

Polymeric seven-coordinated organotin(IV) complexes derived from 5-amino-2-chlorobenzoic acid and in vitro anti-cancer studies

A series of organotin(IV) complexes has been synthesized by reacting 4-piperidine carboxamide with CS2 and R2SnCl2/R3SnCl in 1 : 1 M/L ratio at room temperature. The synthesized complexes were further treated with benzaldehyde to synthesize Schiff bases under stirring. All the complexes were characterized by elemental analysis, FT-IR, 1H and 13C NMR. FT-IR and semi-empirical study confirm the bidentate nature of ligand. The complexes exhibit four-coordinate geometry in solution. Thermodynamic parameters and molecular descriptors were calculated by using semi-empirical PM3 method. HOMO–LUMO calculations show that chlorodiorganotin complexes are more susceptible to nucleophilic attack when compared with triorganotin complexes. Negative heats of formation at 298 K demonstrate that 1, 4, and 7 are thermodynamically stable. The antimicrobial results have shown that complexes containing Schiff base exhibit significantly better activity compared to complexes with carboxamide derivatives.

Synthesis, characterization, HOMO–LUMO study, and antimicrobial activity of organotin(IV) complexes of 4-piperidine carboxamide and its Schiff base

Some tricyclohexyltin(IV) carboxylates, HOOC–R–COOSn(c-C6H11)3 (1) and (c-C6H11)3SnOOC–R–COOSn(c-C6H11)3 (2) [R = 1,2-C6H4 (a), 1,2-C6F4 (b), (Z)-CH=CH (c), CH2CH2 (d)], have been synthesized from reaction of tricyclohexyltin hydroxide with cyclic dicarboxylic anhydrides under microwave irradiation in 1 : 1 and 2 : 1 M ratio, respectively, and characterized by elemental analysis, IR and NMR (1H, 13C, and 119Sn) spectra. Crystal structures of 1a–1c and 2d are determined by X-ray single crystal diffraction. The carboxylate in each compound is monodentate to tin. Compounds 1a and 1c possess a trans-C3SnO2 trigonal bipyramidal geometry with axial positions occupied by carboxylate and carbonyl oxygen of carboxylate of an adjacent molecule forming a one-dimensional chain. Compound 1b is tetrahedral and forms R 2 2(8) hydrogen-bonded dimers by pairs of intermolecular O–H O hydrogen bonds between two carboxylic acid groups. Compound 2d is dinuclear with tin possessing distorted tetrahedral geometry; a trimer supr...

Zhi Liu

Papers

Synthesis, characterization, and cytotoxic activity of tricyclohexyltin(IV) carboxylates derived from cyclic dicarboxylic anhydrides