Self-assembly of extended Schiff base amino acetate skeletons, 2-{[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)]amino}phenylpropionate and 2-{[(E)-1-(2-hydroxyaryl)alkylidene]amino}phenylpropionate skeletons incorporating organotin(IV) moieties: Synthesis, spectroscopic characterization, crystal structures, and in vitro cytotoxic activity
نویسندگان
چکیده
The organotin(IV) compounds, [Ph3SnL H]n Æ nCCl4 (1), [Me2SnL (OH2)] (2), [ Bu2SnL ] (3), [Ph2SnL ]n (4), [Ph3SnL H]n (5) and [Ph3SnL H]n (7) (L 1 = 2-{[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)]amino}phenylpropionate and L 3 = 2-{[(E)-1-(2-hydroxyaryl)alkylidene]amino}phenylpropionate), were synthesized by treating the appropriate organotin(IV) chloride(s) with the potassium salt of the ligand in a suitable solvent, while [Bu2SnL (OH2)] (6) was obtained by reacting the acid form of L 3 (generated in situ) with Bu2SnO. These complexes have been characterized by H, C, Sn NMR, ESI-MS, IR and SnMössbauer spectroscopic techniques in combination with elemental analyses. The crystal structures of 1 and 4–7 were determined. The crystal structures of complexes 1, 5 and 7 reveal that the complexes exist as polymeric chains in which the L-bridged Sn-atoms adopt a trans-R3SnO2 trigonal bipyramidal configuration with R groups in the equatorial positions and the axial locations occupied by a carboxylate oxygen from the carboxylate ligand and the alcoholic or phenolic oxygen of the next carboxylate ligand in the chain. The carboxylate ligands coordinate in the zwitterionic form with the alcoholic/phenolic proton moved to the nearby nitrogen atom. A polymeric zig-zag cis-bridged chain structure is observed for 4, without considering the weak Sn O interaction, the Sn-atom having a slightly distorted trigonal bipyramidal coordination geometry with the two O atoms of the tridentate amino propionate ligand in axial positions. On the other hand, the structure of 6 reveals a monomeric molecule in which the Sn-atom has a distorted octahedral coordination geometry involving the tridentate carboxylate ligand, two n-butyl ligands occupying trans-positions and one water ligand. The in vitro cytotoxic activity of triphenyltin(IV) compounds, viz., 1, 5 and 7 against WIDR, M19 MEL, A498, IGROV, H226, MCF7 and EVSA-T human tumor cell lines are also reported. 2007 Elsevier B.V. All rights reserved.
منابع مشابه
Synthesis, characterization, cytotoxic activity and crystal structures of tri- and di-organotin(IV) complexes constructed from the b-{[(E)-1-(2- hydroxyaryl)alkylidene]amino}propionate and b-{[(2Z)-(3-hydroxy-1- methyl-2-butenylidene)]amino}propionate skeletons
Reactions of potassium b-{[(E)-1-(2-hydroxyaryl)alkylidene]amino}propionates (LHK-LHK) and potassium b-{[(2Z)-(3-hydroxy1-methyl-2butenylidene)]amino}propionate (LHK) with R3SnCl (R = Ph and Bu) and Bu2SnCl2 yielded complexes of composition Ph3SnL H (1), Ph3SnL H (2), Ph3SnL H (3), Bu3SnL H (4), and {[Bu2Sn(L H)]2O}2 (5) and {[ Bu2Sn(L H)]2O}2 (6), respectively. These complexes have been charac...
متن کاملSynthesis, Spectral, Biological and Theoretical Investigation of Some New Sn (IV) Complexes with Schiff Base Ligands Containing NNOS Coordination Sphere
New tin (IV) complexes of empirical formula, [Cl2 Me2 Sn(H2 L)1-3], where ((H2 L)1-3: Methyl-2- {[1-methyl-2-(2-hydroxy-3-methoxyphenyl)methylidynenitrilo]ethyl}amino-1-cyclopentenedithiocarboxylate [H2cd3OMesalMeen], Methyl-2-{[1-methyl-2-(2-hydroxy-4-methoxyphenyl)methylidynenitrilo]ethyl}amino-1-cyclopentenedithiocar-boxylate, [H2 cd4OMesalMeen], Methyl-2-{[1-methyl-2-(2-hydroxy-5-methoxyphe...
متن کاملSynthesis, characterization and crystal structure of a new azo-Schiff base "ethyl 2-((E)-(4-((E)-(4-ethylphenyl)diazenyl)-2-hydroxybenzylidene)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate"
A new azo-Schiff base"Ethyl 2-((E)-(4-((E)-(4-ethylphenyl)diazenyl)-2-hydroxybenzylidene)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate" was prepared by the reaction of "Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate" and "(E)-5-((4-ethylphenyl)diazenyl)-2-hydroxybenz aldehyde" (1:1 molar ratio) in MeOH under reflux condition. The structure of compound was studied by ...
متن کاملSynthesis, Spectroscopic, Molecular Structure, and Antibacterial Studies of Dibutyltin(IV) Schiff Base Complexes Derived from Phenylalanine, Isoleucine, and Glycine
New series of organotin(IV) complexes and Schiff bases derived from amino acids have been designed and synthesized from condensation of 1H-indole-2,3-dione, 5-chloro-1H-indole-2,3-dione, and α-amino acids (phenylalanine, isoleucine, and glycine). All compounds are characterized by elemental analyses, molar conductance measurements, and molecular weight determinations. Bonding of these complexes...
متن کاملTEMPLATE SYNTHESIS, CHARACTERIZATION OF HIGHLY UNSYMMETRICAL TETRADENTATE SCHIFF BASE COMPLEXES OF NICKEL (II) AND COPPER (II)
Nickel (II) and copper (II) complexes of highly unsymmetrical tetradentate Schiff base have been synthesized by the template reaction of half-units N-(1-hydroxy-2-acetonaphtone)-1-amino-2-phenyleneimine (HL) and N-(2-hydroxyacetophenone)-1-amino-2-phenyleneimine (HL1) with the glyoxalphenylhydrazone. The complexes have been characterized by elemental analyses, conductance, IR, 1H NMR and UV spe...
متن کامل