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New trimethyltin(IV) derivatives of dipeptides: synthesis, characteristic spectral studies and biological activity
Author(s) -
Nath Mala,
Pokharia Sandeep,
Eng George,
Song Xueqing,
Kumar Ashok,
Gielen Marcel,
Willem Rudolph,
Biesemans Monique
Publication year - 2004
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.698
Subject(s) - chemistry , trigonal bipyramidal molecular geometry , intramolecular force , stereochemistry , monomer , molecule , medicinal chemistry , mössbauer spectroscopy , crystallography , denticity , tin , nuclear magnetic resonance spectroscopy , organic chemistry , crystal structure , polymer
New trimethyltin(IV) derivatives with general formulae Me 3 Sn(HL), where HL is the monoanion of glycyltyrosine (H 2 L‐1), glycylisoleucine (H 2 L‐2), leucylleucine (H 2 L‐3), leucyltyrosine (H 2 L‐4), alanylvaline (H 2 L‐5), and valylvaline (H 2 L‐6) have been synthesized by the reaction of Me 3 SnCl and the sodium salt of the respective dipeptide with filtration of the NaCl formed. The bonding and coordination behaviour in the compounds synthesized are discussed on the basis of IR and 119 Sn Mössbauer spectroscopic studies in the solid state and multinuclear 1 H, 13 C and 117 Sn magnetic resonance in solution. These investigations suggest that, in the solid state, all the ligands in Me 3 Sn(HL) act as monoanionic bidentates coordinating through the COO − and NH 2 groups. The 119 Sn Mössbauer studies indicate that, for these polymeric derivatives, the polyhedron around tin in Me 3 Sn(HL) is a trigonal‐bipyramid with the three methyl groups in the equatorial positions, while the axial positions are occupied by a carboxylic oxygen and the amino nitrogen atom from the adjacent molecule. The NMR data suggest that, in solution, an equilibrium between solvated and intramolecular coordinated monomeric species exists. The anti‐inflammatory and cardiovascular activities and toxicity of all these compounds have been determined. All the compounds have also been screened against Staphylococcus aureus Mau (29/58), S. aureus Mau (78/71), Bacillus subtilis (18/64), Escherichia coli (326/71), E. coli, Candida albicans (Pn‐10), Microsporum gypseum and Euglena gracillis . All the Me 3 Sn(IV) compounds exhibit good anti‐inflammatory activity. Me 3 Sn(GlyTyr) and Me 3 Sn(GlyIle) display a potent cardiovascular activity and Me 3 Sn(AlaVal) exhibits good antibacterial activity against all the strains chosen. Copyright © 2004 John Wiley & Sons, Ltd.