Organotin(IV) derivatives based on 2-((2-methoxyphenyl)carbamoyl)benzoic acid: Synthesis, spectroscopic characterization, assessment of antibacterial, DNA interaction, anticancer and antileishmanial potentials

Abstract

A series of ten organotin(IV) carboxylate derivatives of 2-((2-methoxyphenyl)carbamoyl)benzoic acid were prepared and confirmed by FTIR, CHN analysis and single crystal XRD (SCXRD) as well as by NMR and mass spectrometry. The microelemental CHN analysis results give a close matching with those of the theoretical values of CHN atoms. The results of the solid state SCXRD for the complex 3 reveals a trigonal bipyramidal geometry (TBG) with slight distortion for the R3SnL derivatives. Further confirmation about the 5-coordinated TBG may also be achieved from the τ value which is 0.87 for the complex 3. It is obvious from the crystal structure of the complex 3 that the involvement of the O1 of the carboxylate moiety and O3 of the amide moiety with Sn atom are responsible for formation of the polymeric structure having 5-coordinated TBG. The comparison of SCXRD value (124.8°) and that of 13C NMR value (123°) for C-Sn-C angle in complex 3 is the best confirmation of 5-coordinated TBG for the R3SnL derivatives. The evaluated compounds interact with DNA by an intercalative type of binding as displayed by the results obtained from UV-vis. and viscosity measurements. The results of the antimicrobial activity of the evaluated compounds in comparison to the standard drugs demonstrate that the tested compounds possess good antimicrobial potentials. The cytotoxicity results obtained against H-157 and BHK-21 cell lines using Sulforhodamine B based method show that compound 1 has the maximum activity among the studied compounds and its activity is comparable to that of the vincristine. The small IC50 value for the compound 1 as compared to the standard antileishmanial drug, Amphotericin B, proves the efficiency of the tested compounds for the treatment of leishmania disease.