Synthesis, Characterization and Antitumour Activity of Di-n-Butyltin Salicyloxamate (original) (raw)
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Synthesis, Characterization and Antitumour Activity of Di-n-Butyl- and Dimethyltin D+ - Camphorates
1998
Metal complexes of 5-carboxy-2-thiouracil with Mn(ll), Co(ll), Ni(ll), Cu(ll), Zn(ll) and Cd(ll) ions were synthesized, characterized, and subjected to a screening system for evaluation of antitumour activity against Sarcoma-180 (S-180) tumour cells. The complexes were characterized by elemental analysis, infrared, electronic spectra, room temperature magnetic measurements and powder X-ray diffraction. The antitumour activity results indicate that some complexes have antitumour activity both in v_jx andj_q vitro against S-180 tumour cells.
Metal-Based Drugs, 1998
Chemotherapy is often the treatment of choice for many types of cancer and the search for new chemotherapeutic agents still plays a major role in the fight against cancer. A reasonable approach in this area deals with use of compounds interacting with DNA and/or inhibiting enzymes critical for cell survival and replication. Amsacrine is one such compound, a well-known antiproliferative agent used to treat some types of cancers including acute adult leukaemia [1]. The poisoning of topo II activity inhibits the relegation process and causes lethal double-strand breaks in DNA, leading to cell cycle arrest and apoptosis. The intercalative property was referred to the planar aromatic system of the acridine moiety [2]. In the same context, acridines have gained strong ground for various biological activities like antimicrobial [3] , antioxidant [4] , anticancer [5-8] , antimalarial [9] , antiinflammatory [10] , analgesic [11] , antileishmanial [12] , antinociceptive [13] , acetylcholinesterase inhibitory [14] and antiherpes [15]. Amsacrine is the best known compound of 9-anilinoacridines series. It was one of the first DNA-intercalating agents to be considered as a topoisomerase II inhibitor. The intercalation process is the strongest type of reversible binding to the double helical DNA in compounds with sufficiently large coplanar aromatic chromophore. Several detailed SAR studies of acridine-based DNA-intercalating agents suggest that the mode of binding is important and the chromophore intercalate with the DNA base
Applied Organometallic Chemistry, 2012
Since organotin complexes have been reported to show fewer side effects relative to other heavy metal anticancer compounds, in the present study we report for the first time four novel organotin(IV) derivatives with the general formula R 2 SnL 2 , where R = methyl (1), n-butyl (2), phenyl (3), benzyl (4) and L = morpholine-1-carbodithioate (MCDT). The newly synthesized ligand was monodentate or bidentate, coordinating through a sulfur atom. The complexes were synthesized by directly mixing, refluxing and stirring the ligand, with diorganotin(IV) dichlorides in a suitable solvent. The complexes were found to be pure and their solid and solution phase structural configuration was investigated by FT-IR, multinuclear NMR (1 H, 13 C, 119 Sn) and mass spectrometry. Complex 2 was also studied for its thermal decomposition by thermogravimetry and differential thermal analysis. The results obtained on the basis of these techniques are in full concurrence with the proposed 1:2 (Sn:L) stoichiometry. The cytotoxic activity of the MCDT and diorganotin(IV) complexes (1-4) was tested against tumor cell lineshuman cervix carcinoma HeLa and human myelogenous leukemia K562and normal immunocompetent cells: peripheral blood mononuclear cells PBMC. Results of bioassay demonstrated that organotin derivatives were in general more active than the anticancer drug cisplatin.
Journal of Applied Toxicology, 2008
SnCl 2 are often tetrahedral, and structurally resemble the active platinum compounds, i.e. cisplatin, and consequently a large number of such complexes have been tested for antitumor activity. A structural correlation with biological activity for diorganotin(IV) complexes has shown that active species are associated with complexes having Sn-N bonds longer than 2.39 Å which in turn determines the formation of a tin-DNA complex. In view of these, a series of diorganotin(IV) dichloride complexes of N-(2-pyridylmethylene)arylamine (nitrogen-chelating ligands) has been synthesized and characterized on the basis of IR, NMR and 119 Sn-Mössbauer studies. In the present study, an attempt was made to determine the comparative antiproliferative and antitumor effect of diorganotin(IV) complexes with different alkyl groups [Me 2 SnCl 2 •L 1 (OTC-1), Et 2 SnCl 2 •L 2 (OTC-2) and n Bu 2 SnCl 2 •L 2 (OTC-3)]. The present study in human lymphocytes demonstrated that these diorganotin(IV) complexes could block the cell cycle progression and induce sister chromatid exchanges (SCEs) significantly, however, with respect to the induction of chromosome aberrations (CAs) it was very mild. Both the levels of p53 and p16 proteins were raised after diorganotin(IV) treatment and such induction was maximum in the OTC-3 treated samples. The antitumor activity was determined in accordance with the US National Cancer Institute (NCI) standard protocol for primary screening in Dalton's lymphoma that was maintained by serial intraperitoneal transplantation. The T/C (treated/control) value was increased (186% with OTC-3) when diorganotin(IV) was given after transplantation. The data suggest that the OTC-3 has better antiproliferative and antitumor activity and endogenous glutathione level has no influence on the effect of OTC-3.
Polyhedron, 2015
Six new organotin(IV) dithiocarbamate complexes of the type R 2 SnL 2 , where (L = p-bromo-N-methylbenzylaminedithiocarbamate and p-fluoro-N-methylbenzylaminedithiocarbamate, and R = dimethyl-, dibutyl-and diphenyl-) have been synthesized in good yields. The isolated ligands and their respective diorganotin complexes were suitably characterized by elemental analysis, FT-IR, 1 H, 13 C and 119 Sn NMR spectroscopies. The crystal structures of three diorganotin(IV) complexes have been determined by X-ray crystallography. The spectroscopic and single crystal X-ray diffraction data illustrate that the dithiocarbamato ligands in the dimethyltin(IV) and diphenyltin(IV) derivatives 1, 2 and 6 are monodentate and the geometry at tin is best described as a distorted tetrahedron. The dimethyltin(IV) and dibutyltin(IV) compounds were evaluated for their in vitro antiproliferative activities. The dibutyltin(IV) complexes showed moderate cytotoxicities toward human leukemic lymphoblastoma Jurkat cells, lymphoblastoma K-562 cells, hepatoblastoma HepG2 cells and mouse fibroblast L929 cells.
European Journal of Medicinal Chemistry, 2010
Six new diorganotin(IV) derivatives of N 0 -(2-hydroxybenzylidene)formohydrazide (H 2 L) with general formula R 2 SnL, where R ¼ Ph (1), Me (2), Bu (3), Oct (4), t-Bu (5), Et (6), and L ¼ [OC 6 H 4 CHNNCHO] have been synthesized and characterized by different analytical techniques. Crystal structure of Me 2 SnL (2) authenticated distorted square-pyramidal geometry around the Sn atom. The CV and UVeVis spectroscopic data indicated intercalation of complexes into DNA with binding affinity varying in the sequence: 3 (1.69 Â 10 4 M À1 ) > 1 (1.10 Â 10 4 M À1 ) > 2 (9.61 Â 10 3 M À1 ). Some of these compounds were found to be good antibacterial, antifungal and leishmanicidal agents.
Natural Product Research, 2017
Simple one-pot syntheses of indenopyrrolopyrimidines and indolopyrrolopyrimidines were achieved via the cyclocondensation of 6-aminouracils and, respectively, ninhydrin and isatin in the presence of catalytic amounts of glacial acetic acid. Similarly, 5,6-diaminouracil derivatives were used as starting materials for the synthesis of indenopteridines and indolopteridines via their reaction with ninhydrin and isatin, respectively. The synthesised compounds were evaluated for antitumour activity against a human hepatocellular carcinoma cell line (HepG2), some showing antitumour activity comparable with 5-fluorouracil and imatinib.
Applied Organometallic Chemistry, 2005
-5methoxy-2-methyl-1H-indole-3-acetate (4) are described. These compounds have been characterized by 1 H, 13 C and 119 Sn NMR spectroscopy in solution and 119 Sn NMR in the solid state, infrared spectroscopy, elemental analysis and X-ray diffraction for compound 1. The growth inhibition effects of compounds 1-4 against the lung adenocarcinoma cell line SK-LU-1 as well as the cervical cancer cell line HeLa were determined. Compounds 1 and 2 exhibit cytotoxic activity, whereas compounds 3 and 4 are inactive.