Synthesis, thermal and antitumour studies of Th(IV) complexes with furan-2-aldehyde-N-phenyl thiosemicarbazone (original) (raw)
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Journal of Inorganic Biochemistry, 1988
Complexes of Mn(II), Fe(III), Fe(II), Co(II), Ni(II), Cu(II), Zn(II) and Pt(II) with 2,6-diacetylpyridine bis(N4-azacyclic thiosemicarbazones), abbreviated as H2L, have been prepared and characterized by elemental analysis, molar conductance, magnetic moments (300-78 K) and spectral studies. On the basis of these studies, a distorted six-coordinate structure for Fe(L)Cl and a distorted five-coordinate structure for M(L) (M = Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II), or Pt(II] are suggested. The ligands undergo deprotonation and appear to coordinate through the thione sulphur, the imine nitrogen and pyridyl nitrogen. All the ligands and metal complexes were screened for their antitumor activity against P 388 lymphocytic leukemia test system in mice, and it was found that a few of them possess significant activity at the dosages used.
Journal of the Iranian Chemical Society, 2005
In the present work, the authors describe the synthesis of some mixed ligand complexes of thorium(IV) derived from 4[N-(2'hydroxy-1'-naphthalidene)amino]antipyrine semicarbazone (HNAAPS) or 4[N-(cinnamalidene)amino]antipyrinesemicarbazone (CAAPS) as primary ligand and diphenyl sulfoxide (DPSO) as secondary ligand with the general composition ThX 4 .n(L).DPSO (n = 1, X = Cl, Br, NCS or NO 3 ; n = 2, X = I or ClO 4 , L = HNAAPS or CAAPS). All the compounds were characterized through elemental analysis, molar conductance, molecular weight, infrared data and thermogravimetric analysis. The infrared studies reveal that the semicarbazones behave as neutral tridentate (N,N,O) while DPSO coordinates through its oxygen atom. The nitrates are bicovalently bonded, while thiocyanates are N-coordinated in these compounds. In conclusion, the coordination number of the central metal ion displays coordination number 7, 8, 9 or 12 depending on the nature of the anionic ligands.
Interdisciplinary Journal of Chemistry, 2016
A series of half-sandwich ruthenium complexes, two containing an arene face-cap and the other a thiacrown ether face-cap were synthesized to investigate the necessity of the arene for anticancer activity in this class of compounds. The complexes are formulated as [(η 6-p-cymene)Ru(dmabTSC)Cl]PF 6 , [(η 6-benzene) Ru(dmabTSC)Cl]PF 6 (arene complexes), and [([9]aneS 3 (dmabTSC)Cl]PF 6 (dmabTSC = dimethylaminobenzaldehye thiosemicarbazone). It was observed that none of the complexes showed good anticancer activity in vitro against HCT-116 and Caco-2 (colon adenocarcinoma) cells. All three complexes can bind strongly to calfthymus DNA with binding constants on the order of 10 5 M-1. In addition they all bind strongly to human serum albumin with binding constants between 10 5 and 10 6 M-1. There appears to be a single binding site on the protein for these complexes. A computational investigation of these complexes and their hydrolysis products was carried out by molecular docking with DNA and topoisomerase II. From this analysis it is noted that the type of face-capping ligand had different effects on the two macromolecules. It is therefore noted that the knowledge gained from this study will be useful in identifying the type of complexes in this class that show useful metallodrug potential.
J Inorg Biochem, 1999
The reaction of [ReOCl 3 (PPh 3 ) 2 ] with N, N-bis(2-mercaptoethyl)benzylamine and 4bromobenzenethiol allowed for the isolation of [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 C 6 H 5 )}-(η 1 -C 6 H 4 Br-4-S)] (1). The reaction of [ReOCl 3 (PPh 3 ) 2 ] with [(HSCH 2 CH 2 ) 2 N(CH 2 C 5 H 4 N)] and the appropriate thiol in chloroform treated with triethylamine has led to the isolation of a series of neutral rhenium complexes of the type [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 X-4-S)] (X = Br (2), Cl (3), F (4), and OCH 3 (5)) and [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 OCH 3 -4-CH 2 S)] (6). Likewise, under similar reaction conditions, the use of the related tridentate ligand, [(HSCH 2 CH 2 ) 2 N(CH 2 CH 2 C 5 H 4 N)], has led to the isolation of a series of rhenium complexes of the type [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 X-4-S)] (X=Br , Cl (8), OCH 3 (9)), as well as [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 Cl-4-CH 2 S)]·0.5CH 3 (CH 2 ) 4 CH 3 (10). These compounds are extensions of the '3+1' approach to the synthesis of materials with the {MO} 3+ core (M=Tc and Re), which have applications in nuclear medicine. The ligands chosen allow systematic exploration of the consequences of para-substitution on the monodentate thiolate ligand [S] and of derivatization of the substituent R on the tridentate aminodithiol ligand [SNS] of the type (HSCH 2 CH 2 ) 2 NR. Such modifications can influence lipophilicity, charge, size and molecular weight of the complex and consequently the biodistribution.
1999
The reaction of [ReOCl 3 (PPh 3 ) 2 ] with N, N-bis(2-mercaptoethyl)benzylamine and 4bromobenzenethiol allowed for the isolation of [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 C 6 H 5 )}-(η 1 -C 6 H 4 Br-4-S)] (1). The reaction of [ReOCl 3 (PPh 3 ) 2 ] with [(HSCH 2 CH 2 ) 2 N(CH 2 C 5 H 4 N)] and the appropriate thiol in chloroform treated with triethylamine has led to the isolation of a series of neutral rhenium complexes of the type [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 X-4-S)] (X = Br (2), Cl (3), F (4), and OCH 3 (5)) and [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 OCH 3 -4-CH 2 S)] (6). Likewise, under similar reaction conditions, the use of the related tridentate ligand, [(HSCH 2 CH 2 ) 2 N(CH 2 CH 2 C 5 H 4 N)], has led to the isolation of a series of rhenium complexes of the type [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 X-4-S)] (X=Br , Cl (8), OCH 3 (9)), as well as [ReO{η 3 -(SCH 2 CH 2 ) 2 N(CH 2 CH 2 C 5 H 4 N)}(η 1 -C 6 H 4 Cl-4-CH 2 S)]·0.5CH 3 (CH 2 ) 4 CH 3 (10). These compounds are extensions of the '3+1' approach to the synthesis of materials with the {MO} 3+ core (M=Tc and Re), which have applications in nuclear medicine. The ligands chosen allow systematic exploration of the consequences of para-substitution on the monodentate thiolate ligand [S] and of derivatization of the substituent R on the tridentate aminodithiol ligand [SNS] of the type (HSCH 2 CH 2 ) 2 NR. Such modifications can influence lipophilicity, charge, size and molecular weight of the complex and consequently the biodistribution.
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 145 (2015) 155–164
A series of two biologically active Schiff base ligands L1 , L2 have been synthesized in equimolar reaction of 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol with thiophene-2-carbaldehyde and furan-2-carbaldehyde. The synthesized Schiff bases were used for complexation with different metal ions like Co(II), Ni(II) and Cu(II) by using a molar ratio of ligand: metal as 1:1 and 2:1. The characterization of Schiff bases and metal complexes was done by 1 H NMR, UV–Vis, TGA, IR, mass spectrometry and molar conductivity studies. The in DFT studies the geometries of Schiff bases and metal complexes were fully optimized with respect to the energy using the 6-31+g(d,p) basis set. On the basis of the spectral studies an octahedral geometry has been assigned for Co(II), Ni(II) and Cu(II) complexes. The effect of these complexes on proliferation of human breast cancer cell line (MCF-7) and human hepatocellular liver carcinoma cell line (Hep-G2) were studied and compared with those of free ligand. The anticancer cell line results reveal that all metal complexes show moderate to significant % cytotoxicity on cell line HepG2 and MCF-7.
European Journal of Medicinal Chemistry
The synthesis, structure, physico-chemical investigation and biological studies of some metal complexes of thiocarbohydrazone ligands are described. The ligand is obtained by condensation of N,N 0-thiocarbohydrazide with 3-acetylcoumarin. The metal complexes of Co(II), Ni(II) and Cu(II) with bis(3-acetylcoumarin)thiocarbohydrazone were synthesized and isolated as solid products and characterized by analytical means as well as by spectral techniques such as FT-IR, 1 H NMR and EPR and UV spectrometry. The ligand acts as bidentate, through NO or NN, neutral in coordinating the M(II) ions. The bonding sites are the azomethine nitrogen, lactone carbonyl oxygen and respective anion counterparts. The metal complexes exhibit either octahedral or distorted octahedral structures. The complexes are found to be soluble in dimethylformamide and dimethylsulphoxide. Molar conductance values in dimethylsulphoxide indicate the non-electrolytic nature of the complexes. The compounds tested in present study have shown promising cytotoxic activity when screened using the in vitro method and at the same time were shown to have good activity when tested using the Ehrlich Ascites Carcinoma model. Preliminary antimicrobial screening shows the promising results against both bacterial and fungal strains.
Structural Chemistry, 2020
The current work reports the synthesis and structural investigation of three novel complexes with 2-acetyl-pyridine-N(4)phenylthiosemicarbazone (HL 1), [Ni(L 1)Cl] (1), [Pd(L 1)Cl] (2) and [Pt(L 1)PPh 3 ]Cl•2MeOH (3). The compounds were structurally characterized by means of single-crystal X-ray crystallography and spectroscopic techniques. All three complexes exhibit tetracoordinated metal centers in a square planar fashion with the thiosemicarbazone acting as a tridentate NNS-donor atoms. Intermolecular hydrogen bonds and π•••π stacking interactions, building supramolecular assemblies in the complexes, were analyzed using the Hirshfeld surface. Mass spectrometry data showed the presence in solution of the characteristic fragmentation with the [M+H] + molecular ion for all complexes. The thermochemical data, estimated by computational chemistry, allowed elucidate the relative intensity of the peaks present in the mass spectrum of the compounds investigated. The antitumor activity and selectivity of the free thiosemicarbazone ligand and their M(II) complexes (M = Ni, Pd, Pt) were evaluated against MCF-7, PBMC, and healthy cells. All compounds studied showed the death of cancer cells observing a great selectivity for the Ni(II) complex.
Journal of the Korean Chemical Society, 2012
New series of metal complexes of Co(II), Ni(II), Cu(II), Zn(II), Pd(II) and Pt(II) with 4-(p-chlorophenyl)-1-(pyridin-2-yl)thiosemicarbazide (HCPTS) have been synthesized and characterized by elemental analyses, magnetic moment, spectra (IR, UV-Vis, 1 H NMR, mass and ESR) and thermal studies. The IR data suggest different coordination modes for HCPTS which behaves as a monobasic bidentate with all metal ions except Cu(II) and Zn(II) which acts as a monobasic tridentate. Based on the electronic and magnetic studies, Co(II), Cu(II), Pd(II) and Pt(II) complexes have square-planner, Ni(II) has mixed stereochemistry (tetrahedral + square planar), while Zn(II) is tetrahedral. Molar conductance in DMF solution indicates the non-ionic nature of the complexes. The ESR spectra of solid copper(II) complex show g|| (2.2221) >g⊥ (2.0899) > 2.0023 indicating square-planar structure and the presence of the unpaired electron in the dx2−y2 orbital with significant covalent bond character. The thermal stability and degradation kinetics of the ligand and its metal complexes were studied by TGA and DTA and the kinetic parameters were calculated using Coats-Redfern and Horowitz-Metzger methods. The complexes have more antibacterial activity against some bacteria than the free ligand. However, the ligand has high anticancer activities against HCT116 (human colon carcinoma cell line) and HEPG2 (human liver hepatocellular carcinoma cell line) compared with its complexes.
Dissymmetric thiosemicarbazone ligands containing substituted.pdf
A serious of new dissymmetric ruthenium(II) carbonyl complexes of the type [Ru(CO)(EPh 3 )(L1e2)] (1e4), [E ¼ P or As; L1 ¼ N 4 -(2-Hydroxy-5-chlorobenzylidene)-2-amino-5-chlorobenzophenone thiosemicarbazone; L2 ¼ N 4 -(2-Hydroxynaphthalene-1-carbaldehyde)-2-amino-5-chlorobenzophenone thiosemicarbazone] have been synthesized and characterized by several spectroscopic studies. The molecular structure of the ligand L1 and the ruthenium(II) carbonyl complexes (2, 4) have been analyzed by single crystal X-ray studies, and found that the ruthenium(II) complexes possess a distorted octahedral geometry. The DNA binding studies such as emissive titration, Ethidium bromide/Methylene blue (EB/MB) displacement assay and viscometry measurements revealed that the ruthenium(II) complexes bound with calf thymus DNA through intercalative mode with relatively high binding constant values. Further, the interactions of the complexes with bovine serum albumin (BSA) were also investigated using fluorescence spectroscopic methods, which showed that the new complexes could bind strongly with BSA. The complexes (1e4) were tested for DNA and BSA cleavage activities, and the results showed that the complexes exhibited good cleavage properties. In addition, the newly synthesized ruthenium(II) complexes possess better in vitro cytotoxic activities against various cell lines (MCF-7, Hop62, MDA-MB-435) and AO/EB staining method showed that these complexes induced apoptosis of MCF-7 cell lines.