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Organotin meclofenamic complexes: Synthesis, crystal structures and antiproliferative activity of the first complexes of meclofenamic acid – Novel anti-tuberculosis agents
Ist Teil von
Journal of inorganic biochemistry, 2009-05, Vol.103 (5), p.738-744
Ort / Verlag
United States: Elsevier Inc
Erscheinungsjahr
2009
Quelle
Access via ScienceDirect (Elsevier)
Beschreibungen/Notizen
The complexes [Me
2(Meclo)SnOSn(Meclo)Me
2]
2 (
2) and [Ph
3Sn(Meclo)] (
3) where HMeclo is meclofenamic acid,
N-(2,6-dichloro-
m-tolylanthranilic acid)], have been prepared and structurally characterized by means of vibrational,
1H and
13C NMR spectroscopies. The crystal structure of complexes (
2) and (
3) have been determined by X-ray crystallography. Three distannoxane rings are present to the dimeric tetraorganodistannoxane of planar ladder arrangement of (
2). The structure is centro symmetric and features a central rhombus Sn
2O
2 unit two additional tin atoms linked at the oxygen atoms. Five- and six-coordinated tin centers are present in the dimer distannoxane. X-ray analysis of (
3) revealed a penta-coordinated structure containing Ph
3Sn coordinated to the chelated carboxylato group. The polar imino hydrogen atom participates in intra-molecular hydrogen bonds. Complexes (
2) and (
3) are self-assembled
via π
→
π, C–H–π, stacking interactions and intra-molecular hydrogen bonds. Meclofenamic acid and [Ph
3Sn(Meclo)] have been evaluated for antiproliferative activity
in vitro against three human cancer cell lines: MCF-7 (human breast cancer cell line), T24 (bladder cancer cell line), A-549 (non-small cell lung carcinoma) and a mouse L-929 (a fibroblast-like cell line cloned from strain L). The [Ph
3Sn(Meclo)] complex exhibited high cytotoxic activity against all the cancer cell lines. Meclofenamic and [Ph
3Sn(Meclo)] were tested for anti-mycobacterial activity against
Mycobacterium tuberculosis H37Rv. The [Ph
3Sn(Meclo)] complex was found to be a promising anti-mycobacterial lead compound, displaying high activity against
M. tuberculosis H37Rv.