Synthesis, structural characterization and in vitro cytotoxicity of organotin(IV) derivatives of heterocyclic thioamides, 2-mercaptobenzothiazole, 5-chloro-2-mercaptobenzothiazole, 3-methyl-2-mercaptobenzothiazole and 2-mercaptonicotinic acid

摘要

Five new organotin(IV) molecules with the heterocyclic thioamides; 2-inereaptobenzothiazole (Hmbzt), 5-chloro-2-mercaptobenzothiazole (Hcmbzt), 3-methyl-2-mercaptobenzothiazole (mmbzt) and 2-mercaptonicotinic acid (H(2)mna) of formulae [(n-C4H9)(2)Sn(mbzt)(2)] (1), [(C6H5)(2)Sn(mbzt)(2)] (2), {(CH3)(2)Sn(cmbzt)(2)].1.7(H2O)} (3), [(n-C4H9)(2)SnCl2(mmbzt)(2).(CH2Cl2)] (4) and {[(C6H5)(3)Sn](2)(nma).[(CH3)(2)CO]} (5) have been synthesized and characterized by elemental analysis, H-1-, C-13-NMR, FT-IR and Mossbauer spectroscopic techniques. Crystal structures of molecules 1, 3 and 5 have been determined by X-ray diffraction at 173(l) K (I and 5) and 293(2) K (3). Compound 1 C22H26N2S4Sn, is monoclinic, space group C2/c, a =44.018(2), b = 8.8864(5), c = 12.8633(7) Angstrom, beta = 104.195(5)degrees, Z = 8. Compound 3 is also monoclinic, space group P2(1)/c and a = 17.128(2) Angstrom, b = 17.919(2) Angstrom, c = 7.3580(10) Angstrom, beta = 98.290(10)degrees, Z=4. In both molecules 1 and 3, two carbon atoms from aryl groups, two sulfur and two nitrogen atoms from thione ligands form a distorted octahedral geometry around tin(IV) with trans-C-2, cis-N-2, cis-S-2 configurations. Compound 5 C45H39NO3SSn2 is monoclinic, space group P2(1), a=9.1148(2) Angstrom, b=29.2819(6), c=15.5556(4) Angstrom, beta=106.285](9)degrees, Z=4. Complex 5 contains two I(C6H5)3Sn(IV)] moieties linked by a double deprotonated 2-mercaptonicotinic acid (H(2)mna). Both tin(IV) ions are five coordinated. This complex is the an example of a pentacoordinated Ph3SnXY system with an axial-equatorial arrangement of the phenyl groups at Sn(1) atom. Compounds 1, 3 and 5 were tested for in vitro cytotoxicity against the cancer cell line of sarcoma cells (mesenchymal tissue) from the Wistar rat, polycyclic aromatic hydrocarbons (benzo[a]pyrene) carcinogenesis. Compound 5 exhibits strong cytotoxic activity, while complexes 1 and 3 show less cytotoxic activity.