Abstract
Organotin(IV) thiocarboxylates R2SnL2 (R = Me: 1: Ph: 2)/R2(Cl)SnL (R = n-Bu: 3; Ph: 4)/R3SnL (R = Me: 5; n-Bu: 6; Ph: 7), where L = 4-(2-hydroxyethyl)piperazine-1-carbodithioate, have been synthesized by stirring together 1,2-hydroxyethylpiperazine and CS2 in methanol, and then refluxing with a di-/triorganotin chloride. The synthesized products have been characterized by various spectroscopic (IR, 1H NMR, 13C NMR, EI-MS) techniques and single crystal XRD. FT-IR data indicate bidentate binding of the ligand. The magnitude of 2J(119Sn–1H) demonstrated a skew trapezoidal environment around tin(IV) in 1, whereas the metal geometry in 5 was between distorted tetrahedral and trigonal bipyramidal in solution. 13C NMR revealed four- and five-coordinate environments in 6 and 7, respectively, in non-coordinating solvent. EI-MS data agreed very well with the structural skeleton of the products. Single crystal XRD study has shown skew trapezoidal- and trigonal-bipyramidal Sn(IV) in 1 and 7, respectively. Compound 6 interacted with salmon sperm DNA (SS-DNA) with significant hypochromic effect and an intercalating mode of binding. Diorganotin(IV) derivatives (2 and 3) generally exhibited poor antibacterial/antifungal potential as compared to their trialkyltin(IV)/triaryltin(IV) counterparts (5 and 6). The in vitro hemolytic activities show that average lysis of human red blood cells caused by 1–7 was significantly lower compared to triton X-100 (positive control, 100% lysis) and not very much higher than PBS (negative control, 0% lysis).
Published Version
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