Salicylaldehyde Benzoylhydrazone Research Articles

Synthesis and Investigation of Mixed‐Ligand Transition Metal Complexes of Alkyl Dithiocarbonate and Benzoylhydrazine or Benzoylhydrazone Derivatives

Mixed‐ligand complexes of the types [Ni(Etdtcn)(BH)], [Ni(Budtcn) (BeBH)], and [M(Rdtcn)(salBH)], where M = Co(II), Ni(II), or Cu(II); R = methyl (Me), ethyl (Et), propyl (Prop) or butyl of the dithiocarbonate (Bu); dtcn = dithiocarbonate group; BH = benzoyl‐hydrazine anion, BeBH = benzaldehyde benzoylhydrazone anion, and salBH = salicylaldehyde benzoylhydrazone anion have been synthesised. Elemental analyses, molar conductivities, and spectral (IR, UV, and mass) studies have been used to elucidate the structure of the metal complexes. HBH and HBeBH coordinate in the enol form as bidentate ligands forming a square‐planar structure around Ni(II). Moreover, the HsalBH ligand behaves as tridentate anion with all metal ions and an octahedral structure for these complexes is proposed. The three ligands and some of their complexes were screened against three species of bacteria, namely B. cereus (G +ve), P. aeruginosa (G −ve), and S. aureus (G +ve) and five types of fungi, A. flavus, A. fumigatus var. albus, A. niger, F. oxysporum or C. tropicum. The HsalBH ligand has shown high activity against bacteria and fungi, probably due to the presence of a hydroxyl group in this ligand.

Structure of di(salicylaldehyde benzoylhydrazonato) zinc (II), an unusual staircase polymeric structure formed via E → Z isomerization on complexation

Abstract A bicomplex of salicylaldehyde benzoylhydrazone (SBH) with Zn(II) was synthesized in ethanol and single crystals were obtained in DMSO. The compound crystallizes in the orthorhombic system with the space group Pna21(33) and crystal data: a = 22.573(3)Å, b = 6.1208(5) Å, c = 17.881(2) Å, V = 2470.5(5) Å3, Z = 4, d(calc) = 1.462 g⋅cm–3, (2633 reflections with I > 2 σ(I); final R = 0.0509; R w = 0.1099). The asymmetric unit is a nearly planar bicomplex built up from one Zn atom linked to two monodeprotonated SBH ligands. The compound can be described as formed of chains extended along the b axis. This linear polymeric character results from the linking of each asymmetric unit to two neighbouring ones via four (2x2) covalent Zn-O bonds involving three Zn atoms and four phenolic oxygens. These covalent bonds are related to the very unusual Z configuration of the ligand. The three-dimensional cohesion of the compound is obtained by van der Waals forces be-tween the polymeric chains.

Synthesis, Characterization, Thermal and Electrical Properties of Yttrium(III) and Lanthanide(III) Complexes of Salicylaldehyde Benzoyl Hydrazone

Complexes of Y(III), La(III), Pr(III), Nd(III), Sm(III), Gd(III), Tb(III) and Dy(III) with salicylaldehyde benzoyl hydrazone, (C6H5CONHN˭CHC6H4OH), abbreviated as H2L, have been synthesized and characterized. The analytical data are suggestive of 2:3 metal: ligand stoichiometry in the complexes except in the case of Y(III), which is a 1:1 complex. A dehydration study at two temperatures, 110° C and 150° C, indicates water molecules both in the lattice and co-ordination sphere of the metal ions. Magnetic moments, IR spectra, electronic spectra and 1H NMR spectra have been recorded to establish the bonding sites of the ligand. The complexes are coloured, soluble in methanol, dimethyl sulfoxide, dimethyl formamide and insoluble in benzene, chloroform and acetonitrile. Solid state conductance at various frequencies shows the semiconducting nature of the complexes. Solution state conductance indicates their non-electrolyte nature. Optical band gap measurements on a representative complex, Dy2(L)3.12H2O show that the complex is a direct band gap material. X-ray analyses show that the structures of most of the complexes are orthorhombic.

Cytotoxicity of salicylaldehyde benzoylhydrazone analogs and their transition metal complexes: quantitative structure–activity relationships

A series of salicylaldehyde benzoylhydrazone derivatives, their copper(II) complexes and a range of transition metal complexes of the unsubstituted ligand has been synthesized and evaluated for cytotoxicity against a human adenocarcinoma cell line. A QSAR analysis revealed ligand cytotoxicity is strongly correlated with electronic and transport factors and can be modeled by treating each `half' of the molecule as an isolated unit. Activity increases when substituents in the benzoyl ring were electron withdrawing whereas, for the salicylaldehyde ring, electron donation was required. The cytotoxicity of the Cu(II) complexes was greater than, and paralleled the ligands. Activity for the transition metal complexes of the unsubstituted ligand mirrored charge density on the metal.

Syntheses and characterization of four novel monooxovanadium(v) hydrazone complexes with hydroxamate or alkoxide ligand

Four novel monooxovanadium(V) hydrazone complexes, [VOL 1(Hshi)] (1), [VOL 1(bz)] (2), [VOL 2(bz)]·CH 2Cl 2 (3), and [VOL 2(OCH 3)(CH 3OH)]·CH 3OH (4) (H 2L 1=salicylaldehyde benzoylhydrazone, H 2L 2=o-vanillin benzoylhydrazone, H 2shi=salicylhydroxamic acid, Hbz=benzohydroxamic acid), were prepared and characterized by IR, Raman, UV, 1H NMR spectra, cyclic voltammetry measurements and X-ray diffraction. The geometry around the vanadium atoms is a distorted VO(ONO)(OO) octahedron in complexes 1, 2 and 3, while the geometry is a distorted VO(ONO)(O)(O) octahedron in 4. The VO bond distance is 1.574(4), 1.593(5), 1.594(4) and 1.577(4) Å for complexes 1, 2, 3 and 4, respectively. In complexes 1, 2 and 3, the O, N, O atoms of a tridentate hydrazone ligand and one oxime oxygen atom of a bidentate hydroxamate ligand are coordinated to the vanadium(V) atom, forming an equatorial plane. In complexes 1, 2 and 3, the axial position trans to the oxo group is occupied by the carbonyl oxygen atom of the hydroxamate ligand, but not by the oxime oxygen atom. The bond distances in the equatorial plane in the title complexes follow the order: alkoxide oxygen<phenoxide oxygen, oxime oxygen<enolic oxygen<imine nitrogen. The complexes 1, 2 and 3 represent the first structural examples of vanadium complexes containing both hydrazone and hydroxamate ligands.

Partition coefficients of the iron (III) complexes of pyridoxal isonicotinoyl hydrazone and its analogs and the correlation to iron chelation efficacy. Correction of some reported partition coefficients

Pyridoxal isonicotinoyl hydrazone (PIH), salicylaldehydebenzoyl hydrazone (SBH), and their analogschelate iron(III) and show promise asorally effective drugs for treating diseases of iron overload. Theirbiological activity isrelated to their lipophilicity, as measured by their partition coefficients P betweenn-octanoland water. However, the method of calculating log P described in an article in this journal(Edwardet al. 1995; BioMetals, 8, 209-217) is faulty for compounds such as PIH, SBH andtheir analogs whichcontain adjacent hydrophilic groups. Consequently, the calculations reportedin the article, based on erro-neouslog P values of the chelating molecules, giveerroneous log P values of the iron(III) complexes. Thechelators most effective inmobilizing 59 Fe from reticulocytes have log P < 2.8, not log P < 0 and theiron(III)complexes of the most effective chelators have log P < 3.1, not log P < 0.

Antitumour copper(II) salicylaldehyde benzoylhydrazone (H 2sb) complexes: physicochemical properties and the single-crystal X-ray structures of [{Cu(H 2sb)(CCl 3CO 2) 2} 2] and [{Cu(Hsb) (ClO 4) (C 2H 5OH)} 2] and the related salicylaldehyde acetylhydrazone (H 2sa) complex, [Cu(Hsa)Cl(H 2O)]·h 2O

Copper(II) complexes of the antitumour ligand salicylaldehyde benzoylhydrazone (H 2sb) have been prepared. In the presence of strong acids, complexes of the neutral ligand were isolated: [{Cu(H 2sb)X 2} 2]· nH 2O (X = Br, n X = CCl 3CO 2, n = 0) and [Cu(H 2sb)Cl 2(H 2O)]. In weakly acid or neutral media, monoanionic compounds separated: Cu(HsB)X 2· nH 2O] (X = Cl,Br, NO 3, 0.3SO 4, n = 0; X = ClO 4, n = 1). With base only the highly insoluble dianionic complex [{Cu(sb)} 2] was isolated. Also prepared was the related anionic ligand complex [Cu(Hsa)Cl(H 2O)]·H 2O (H 2sa = salicylaldehyde acetylhydrazone). The complexes have been characterised by a range of physicochemical techniques and the crystal and molecular structures of [{Cu(H 2sb)(CCl 3CO 2) 2} 2], [{Cu(Hsb)ClO 4(C 2H 5OH)} 2] and [Cu(Hsa)Cl(H 2O)]·H 2O, determined by single-crystal X-ray diffraction studies. Crystals [{Cu(H 2sb)(CCl 3CO 2) 2} 2] are triclinic, space group P 1 , with = 10.130(2), b = 11.660(2), c = 11.876(2)r α = 67.07(2), β = 109-09(2) γ = 107.84(2)° and Z = 2. The complex is a centrosymmetric dimer, the monomeric units being bridged through the phenol oxygen. The copper coordination is tetragonal with the equatorial donor atoms coming from the tridentate ‘ONO’ donor ligand and the symmetry-related phenol oxygen. The more weakly bound axial donor oxygens are from the coordinated trichloroacetates. Crystals of [Cu(Hsb)ClO 4(C 2H 5OH) 2] are monoclinic, space group P2 1/ c, with a = 11.2281(8), b = 7.9129(4), c = 21.043(1) ;rA β = 98.560(6)°✓ and Z = 4. This complex is also a centrosymmetric dimer, the monomeric units being bridged through the phenoxy oxygen. The copper coordination is tetragonal with the equatorial donor atoms coming from the tridentate ‘ONO’ ligand and the symmetry related phenoxy oxygen. The more weakly bound axial donor oxygens are supplied by the ethanol and perchlorato moieties. Crystals of [Cu(Hsa)Cl(H 2O)]·H 2O are monoclinic, space group P2 1/ c, with a = 7.4877(4), b = 15.5806(7), c = 10.5208(3) A ̊ , β = 103.56(4)° and Z = 4 . The complex is monomeric with the copper(II) adopting a square-pyramidal coordination. The four in-plane donors are provided by the tridentate ‘ONO’ donor Hsa and an oxygen from a coordinated water molecule; the axial site is occupied by the chloride ion. Most of the complexes have low magnetic moments and are assigned dimeric side-by-side structures. Powder ESR spectra have g 1 and g ✓ resolved often with ΔM = 2 transitions present.

The Potential of Iron Chelators of the Pyridoxal Isonicotinoyl Hydrazone Class as Effective Antiproliferative Agents II: The Mechanism of Action of Ligands Derived From Salicylaldehyde Benzoyl Hydrazone and 2-Hydroxy-1-Naphthylaldehyde Benzoyl Hydrazone

AbstractWe have recently screened 36 analogues of the lipophilic iron (Fe) chelator, pyridoxal isonicotinoyl hydrazone (PIH), for their antiproliferative effect (Richardson et al, Blood 86:4295, 1995). Of these compounds, 1 chelator derived from salicylaldehyde benzoyl hydrazone (206) and 4 ligands derived from 2-hydroxy-1-naphthylaldehyde benzoyl hydrazone (308, 309, 311, and 315) showed pronounced antiproliferative activity, being far more effective than desferrioxamine (DFO). The present study was designed to investigate in detail the mechanism of action of these PIH analogues in a variety of neoplastic cell lines. This investigation showed that the analogues were far more active than DFO at inhibiting cellular proliferation and 3H-thymidine, 3H-leucine, and 3H-uridine incorporation. Additional experiments showed that, in contrast to DFO, the 5 analogues were potent at preventing 59Fe uptake from transferrin (Tf ) and increasing 59Fe release from cells at concentrations as low as 10 μmol/L. Examination of the distribution of 59Fe in neoplastic cells using native polyacrylamide gel electrophoresis (PAGE)/59Fe-autoradiography showed that most of the 59Fe taken up from Tf was incorporated into ferritin, although 3 other previously unrecognized components (bands A, B, and C) were also identified. Band C comigrated with 59Fe-citrate and was chelated on incubation of neuroblastoma cells with DFO, PIH, or the PIH analogues, with this compartment being the main intracellular target of these ligands. Further work showed that the effects of the chelators at inducing characteristics consistent with apoptosis or necrosis were cell line-specific, and while DFO increased the percentage of cells in the Go/G1 phases in all cell types, the effect of analogue 311 on the cell cycle was variable depending on the cell line. This study provides further evidence for the potential use of these Fe chelators as anticancer agents.

Synthesis and antimicrobial activity of 3d-element coordination compounds with salicylaldehyde benzoylhydrazone

Synthesis and antimicrobial activity of 3d-element coordination compounds with salicylaldehyde benzoylhydrazone

Salicylaldehyde Benzoyl Hydrazone

The crystallographic characterization of N-(2-hydroxybenzylideneamino)benzamide, C 14 H 12 N 2 O 2 , reveals quasi coplanarity of the whole molecular skeleton, localization of the double bonds in the central -C=N-N-C=O chain, which has an E configuration with respect to the double bond of the hydrazone bridge, and an amide trans,s-cis configuration around the single N-N bond. The molecules are held together by hydrogen bonds linking them into layers along the [100] direction.

Infrared study of complexes between iron, salicylaldehyde benzoyl hydrazone and seven analogous derivatives

An i.r. study of Fe complexes prepared from salicylaldehyde benzoyl hydrazone and seven similar chelating agents allowed the assignment of some iron-ligand bands. The amide I and Φ—O band shifts indicate that the ligand O atoms are directly linked to Fe. The analogy between FeII and FeIII complexes in the mid-i.r. range and the chiefly identical frequencies in the far-i.r. range provide evidence that oxidation of FeIIhas occurred. The bands directly involved in complexation are shifted compared to the free hydrazones, and all are medium or weak.

Hexafluorosilicate coordination to the antitumour copper(II) salicylaldehyde benzoylhydrazone (H 2L) system: single-crystal X-ray structure of [{Cu(HL)H 2O} 2SiF 6]·2H 2O

The complex [{Cu(HL)H 2O} 2SiF 6]·2H 2O (H 2L = salicylaldehyde benzoylhydrazone) has been prepared from the reaction of CuF 2·2H 2O in concentrated HF with ethanolic solution of H 2L. SiF 6 2− was generated by the in situ reaction of fluoride on silica. The complex has been characterized by a range of physicochemical techniques and the crystal and molecular structure determined by single-crystal X-ray diffraction. The crystals of [{Cu(HL)H 2O} 2SiF 6]·2H 2O are monocliic, space group C2/ c, with a = 13.677(5), b = 11.876(3), c = 20.3 A ̊ , β = 105.92(3)° and Z = 4. The complex is a discrete centrosymmetric dimer, the monomeric units being bridged by the coordinated SiF 6 2− anion with the Si lying on the inversion centre. The copper atom has a distorted square-pyramidal geometry with three donor atoms (ONO) from the tridentate monoanionic HL − ligand and the fourth in-plane donor (O), from a water molecule. The fifth position is occupied by a less strongly bound fluorine from the bridging SiF 6 2− anion. Alternate stacking of the dimeric units which would allow overlap of π electron density as well as H bonding involving all of the hexafluorosilicato F atoms appears to be important for the stability of the complex in the solid.

Infrared Study of Seven Potential Siderophores Analogous to Salicylaldehyde Benzoyl Hydrazone (SBH)

Abstract Seven siderophores which differ from salicylaldehyde benzoyl hydrazone by only one substituent on the benzoyl moiety are studied with infrared Spectroscopy between 2000 and 1100 cm−1. The shift of the amide-I band and the intensity variations of cycle stretching bands are specially discussed according to the nature of the substituents.

ChemInform Abstract: Synthesis and Structural Characterization of Cobalt(II) Complexes of Some Salicylaldehyde Benzoylhydrazones.

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Synthesis and Structural Characterization OP Cobalt (II) Complexes of Some Salicylaldehyde Benzoylhydrazones

Abstract The following hydrazones derived from substituted benzoylhydrazides and salicylaldehyde have been synthesized and used in preparing some cobalt (II) complexes: salicylaldehyde-4-chlorobenzoylhydrazone (ChsH), 4-nitrobenzoylhydrazone (NhsH), 2-hydroxybenzoylhydra-zone (ShsH), and isonicotinoyl (or 4-pyridinoyl) hydrazone (IhsH). The ligands undergo deprotonation in ethanolic alkaline solution to form monomeric or dimeric complexes. In neutral solution, they form adduct complexes. Complexes with the following stoichiometry have been isolated and characterized by elemental analyses, i.r., electronic spectra, conductance, molecular mass and magnetic susceptibility measurements: [Co(XhsH)Br] nH2O (X = C, I, N or S; n = 0, 2 or 5), [Co(Xhs)2(X = C or S), [Co(Xhs)]2.nH2O (X = C or I; n = 0 or 6). The bonding and probable structures of the complexes are discussed on the basis of the spectral and magnetic data.

Mixed-Ligand Uranyl(VI) Complexes of Multidentate Hydrazones and Bidentate (N,N′) Chelating Ligands

Abstract Uranyl(VI) complexes of the mixed ligands of benzoylhydrazide, salicylaldehyde benzoylhydrazone and the neutral bidentate ligands, a,a′-bipyridyl, 1,10-phenanthroline, o and m-phenylene-diamine having the general formulas [(UO2)(BAH)2(N,N′)X2] and [(UO2)(SB)(N,N′)X]X, where X = Cl, Ac or NO3, BAH and SB stands for benzoyl hydrazide and salicylaldehyde benzoylhydrazone and N,N′ stands for the bidentate ligands. The complexes have been characterized on the basis of elemental analyses, electrical conductance, IR and electronic spectra.

Étude Infrarouge du Pyridoxal Isonicotinoyle Hydrazone Et de Composes Analogues

AbstractInfrared spectra have been obtained for pyridoxal isonicotinoyl hydrazone, pyridoxal benzoyl hydrazone, salicylaldehyde isonicotinoyl hydrazone and salicylaldehyde benzoyl hydrazone. Vibrational assignments are proposed mainly in the 2000‐1200 cm−1 region. Evidence is given that a intramolecular bond exists between the phenolic hydroxyl and the nitrogen of imine group. Trans amide III band located near 1550 cm−1 presents a drastic shift from usual results (more than 50 cm−1). Conformational equilibrium is discussed with AM1 and ab‐initio methods. IR and NMR (NOE measurements) studies show that one conformation seems to be predominant.

Kinetic and thermodynamic study of complex formation between iron(II) and pyridoxal isonicotinoylhydrazone and other synthetic chelating agents

In neutral aqueous media pyridoxal isonicotinoylhydrazone (PIH), pyridoxal benzoylhydrazone (PBH), salicylaldehyde isonicotinoylhydrazone (SIH), and salicylaldehyde benzoylhydrazone (SBH), which show interesting potential for iron mobilization in living cells, form bicomplexes with Fe(II) in two kinetically distinguishable steps. the first is fast and is ascribed to complex formation with a single ligand

An ion-pair reversed-phase HPLC-fluorimetric system for ultratrace determination of aluminium with salicylaldehydebenzoylhydrazone

An ion-pair HPLC fluorimetric determination of Al(III) at trace level has been developed, with salicylaldehydebenzoylhydrazone (SAB) as a precolumn reagent. The highly fluorescent AlSAB chelate (λ ex 390.8 nm, λ em 458.1 nm) is separated on a LiChroCART RP-18 column with an eluent consisting of 3.1 × 10 − m tetrabutylammonium bromide, 1 × 10 4̄ m disodium EDTA and 5 × 10 −3 m sodium acetate in aqueous 42% w/w acetonitrile solution. The detection limit for Al is 1.5n M (40 pg/ml) in a 100-μl injection. The spectrophotometric detection limit at 390 nm is 0.3 ng/ml for 0.005 full-scale absorbance range. The selectivity is excellent and the method is useful for routine quality-control applications, such as determination of Al in tap water and in alkali pellets (LiOH, NaOH and KOH).

ChemInform Abstract: Synthesis, Characterization and Antitumor Activity of Iron(II) and Iron(III) Complexes of 3‐ and 5‐Substituted Salicylaldehyde Benzoyl Hydrazones.

AbstractThe tridentate Schiff base ligands, prepared by condensation of benzoylhydrazide with the various substituted salicylaldehydes, react in ethanol under reflux with FeSO4·7 H2O or FeCl3 to yield the Fe(II) and Fe(III) complexes (I)‐(III) (no yields given).