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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis, structural characterization and in vitro antitumour properties of triorganoantimony(V) disalicylates: Crystal and molecular structures of [5-Y-2-(ho)-C6H3COO]2SbMe3 (Y=H, Me, MeO) (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 9 (1995), S. 597-607 
    Details
    ISSN: 0268-2605
    Keywords: organoantimony ; carboxylate ; crystal structure ; antitumour ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Triorganoantimony(V) salicylates, [5-Y-2-(HO)-C6H3COO]2SbR3 (R=Me, Ph; Y=H, Me, MeO), were obtained by reacting R3SbCl2 with the appropriate sodium salt. The compounds have been characterized by IR, MS, 1H and 13C NMR spectroscopy. The molecular structure of the three substituted trimethylantimony(V) disalicylates has been determined by X-ray diffraction. The salicylate ligands are mono-coordinated to antimony through an oxygen atom of each carboxylate, leading to a trigonal bipyramidal geometry, with the antimony-methyl groups in equatorial positions and the oxygen atoms in axial positions. The trimethylantimony compounds tested in vitro against a series of human tumour cell lines were found to be inactive.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/aoc.590090715
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  • 2
    Electronic Resource
    Electronic Resource
    Di(n-butyl)tin bis(dihydroxybenzoate)s: Synthesis, spectroscopic characterization and in vitro antitumour activity (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 9 (1995), S. 251-257 
    Details
    ISSN: 0268-2605
    Keywords: butyltin ; hydroxybenzoate ligand ; synthesis ; anticancer ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Six di(n-butyl)tin(IV) and two dimethyltin(IV) bis-(dihydroxybenzoate)s were synthesized and characterized by 1H, 13C and 119Sn NMR and Mössbauer spectroscopy. Five of the di(n-butyl)tin compounds were screened in vitro against six human tumour cell lines, MCF-7, EVSA-T, WiDr, IGROV, M19 and A498. They are more active than carboplatin, cisplatin and 5-fluorouracil against all cell lines and of comparable activity or better than methotrexate. All dihydroxybenzoates with an ortho-bydroxyl group are more active against MCF-7 cells than substituted salicylates screened previously.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/aoc.590090308
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  • 3
    Electronic Resource
    Electronic Resource
    Organostannate derivatives of dicyclohexylammonium hydrogen 2,6-pyridinedicarboxylate: solution/solid-state 13C,119Sn NMR and in vitro antitumour activity of bis(dicyclohexylammonium) bis(2,6-pyridinedicarboxylato)dibutylstannate, and the crystal structure of its monohydrate (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 11 (1997), S. 39-45 
    Details
    ISSN: 0268-2605
    Keywords: organotin ; solid-state NMR ; crystal structure ; antitumor activity ; Chemistry ; Industrial Chemistry and Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bis(dicyclohexylammonium) bis(2,6-pyridinedicarboxylato)dibutylstannate is assigned seven-fold coordination at tin on the basis of its 119Sn CP/MAS NMR chemical shift (δ=-424.9 ppm). The assignment has been corroborated by a crystal structure determination of its monohydrate, whose tin atom has the trans-C2SnNO4 pentagonal bipyramidal [Sn-C=2.040(9), 2.067(8) Å; C-Sn-C =168.9(5)°] geometry. One 2,6-pyridine- dicarboxylato group chelates to the tin atom (Sn-O=2.234(4), 2.260(4); Sn-N =2.279(5) Å) whereas the other binds through only one carboxyl -CO2 end (Sn-O=2.416(5), 2.441(5) Å). Hydrogen bonds link the cation and the stannate into a linear chain parallel to the b-axis. The lattice water molecule is hydrogen-bonded to the free carboxyl end. The anhydrous compound showed higher in vitro antitumor activity than those of carboplatin and cisplatin when screened against breast (MCF-7, EVSAT), colonic (WiDr), ovarian (IGROV) and renal (A498) carcinoma, and melanoma (M19 MEL) cell lines. © 1997 by John Wiley & Sons, Ltd.
    Additional Material: 2 Ill.
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis, characterization and in-vitro antitumour activity of dibutyltin carboxylates involving the perfluorophenyl moiety: Crystal structure of the dimeric bis[(4-fluoro- and pentafluoro-benzoato)di-n-butyltin] oxides (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 9 (1995), S. 639-648 
    Details
    ISSN: 0268-2605
    Keywords: organotin ; carboxylate ; crystal structure ; distannoxane ; antitumour ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Crystal structure determinations of {[(F5C6COO)Bu2Sn]2O}2 and {[(4-F-C6H4COO)-Bu2Sn]2O}2 show that the structures are similar and feature central Bu4Sn2O2 units with two Bu2Sn groups connected by bridging oxygen atoms. Each pair of exo- and endo-cyclic tin atoms is linked by an almost symmetrically bridging carboxylate group, with the two remaining groups attached to the exocyclic tin atom only. Crystals of {[(F5C6COO)Bu2Sn]2O}2 are triclinic, space group P1, with unit cell dimensions a = 12.425(3) Å, b = 13.090(5) Å, c = 11.697(3) Å, α = 95.31(3)°, β = 93.28(2)°, γ = 113.01(2)°, V = 1734(1) Å3, Z = 1. Crystals of {[(4-F-C6H4COO)Bu2Sn]2O}2, are also triclinic, space group PI, a = 12.599(6) Å, b= 25.359(4) Å, c = 11.480(4) Å, α = 91.44(3)°, β = 114.77(3)°, γ=97.43(3)°, V=3289(2) Å3, Z=2. The structures were refined to final R= 0.046, Rw = 0.046 for 4312 reflections with I≥ 3.0 σ(l) for {[(F5C6COO)Bu2Sn]2O}2 and R=0.061, Rw=0.068 for 4112 reflections with l≥3.0 σ(l for {[(4-F-C6H4COO)Bu2Sn]2O}2.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/aoc.590090720
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis, characteristic spectral studies and in vitro antimicrobial and antitumour activities of organotin(IV) complexes of Schiff bases derived from amino-acids (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 11 (1997), S. 727-736 
    Details
    ISSN: 0268-2605
    Keywords: organotin(IV) ; Schiff base ; amino-acid ; antimicrobial activity ; antitumour activity ; Chemistry ; Industrial Chemistry and Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Equimolar reactions of dibutyltin(IV) oxide with Schiff bases derived from amino-acids led to the formation of a new series of dibutyltin(IV) complexes of general formula, Bu2SnL [L=dianion of tridentate Schiff bases derived from the condensation of 2-hydroxy-1-naphthaldehyde or acetyl acetone with glycine (L-1), L-β-alanine (L-2), DL-valine (L-3), DL-4-aminobutyric acid (L-4), L-methionine (L-5), L-leucine (L-6) and phenylglycine (L-7)]. An attempt has been made to prove the structures of the resulting complexes on the basis of elemental analyses, conductance measurements and electronic, IR, multinuclear magnetic resonance (1H, 13C and 117Sn) and 119Sn Mössbauer spectral studies. The complexes have been tested against various bacteria [Streptococcus faecalis, Klebsiella pneumoniae, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus penicillin resistance (2500 units)] and fungi (Candida albicans, Cryptococcus neoformans, Sporotrichum schenckii,Trichophyton mentagrophytes and Aspergillus fumigatus). All the complexes showed moderate activity. The cytotoxicity of a few compounds has been screened in vitro against seven human tumour cell lines, viz. MCF-7, EVSA-T, WiDr, IGROV, M19 MEL, A498 and H226. The activities found experimentally were better than those obtained for cisplatin and carboplatin © 1997 John Wiley & Sons, Ltd.
    Additional Material: 2 Ill.
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  • 6
    Electronic Resource
    Electronic Resource
    Organotin gibberellates: Synthesis, spectroscopic characterization and antitumour activity (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 12 (1998), S. 855-859 
    Details
    ISSN: 0268-2605
    Keywords: butyltin ; phenyltin ; gibberellates ; antitumour ; Chemistry ; Industrial Chemistry and Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis and characterization of di-n-butyl-, tri-n-butyl- and triphenyltin gibberellates are reported. Their antitumour activities in vitro against a panel of seven human tumour cell lines are given and compared with those of drugs used clinically. Copyright © 1998 John Wiley & Sons, Ltd.
    Additional Material: 2 Ill.
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  • 7
    Electronic Resource
    Electronic Resource
    Gradient-Enhanced 2D Multinuclear NMR and X-ray Diffraction Studies of Reaction Products of Dimethyltin(IV) Salicylaldoximate with Chiral Alcohols (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 1467-1472 
    Details
    ISSN: 1434-1948
    Keywords: Dimethyltin salicylaldoximates ; Chiral ligands ; Proton-tin HMQC NMR ; X-ray structure ; Trinuclear microclusters ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The complex {[(CH3)2Sn]2[(CH3)2SnO](OCH3)(HONZO)(ONZO)} (3) [ONZOH is the oximate residue, o-(-ON=CH-C6H4-OH), HONZO the corresponding phenolate residue, o-(HON=CH-C6H4-O-), and ONZO the dibasic species o-(-ON=CH-C6H4-O-), all derived from salicylaldoxime, o-(HON=CH-C6H4-OH)] reacts with an excess of racemic (d,l)-2-methyl-1-butanol to afford the μ2-substitution product 5a {[(CH3)2Sn]2[(CH3)2SnO][OCH2CH(CH3)CH2CH3](HONZO)(ONZO)]}. Crystallographic characterisation of the trinuclear microcluster 5a shows the presence of the monobasic HONZO ligand in a tridentate μ2-O,N mode and of the dibasic ONZO ligand in a tridentate O,N,O mode. This coordination mode leads to one seven-coordinate and two five-coordinate tin centers that are linked by a μ3-oxo function. The coordination geometries are distorted pentagonal bipyramidal and trigonal bipyramidal, respectively. The two low-coordinate tin atoms are linked by the alkoxide ion. The corresponding chiral (S)-2-methyl-1-butanol reacts analogously to yield 5b. By contrast, reaction of 3 with chiral secondary alcohols (2-butanol or 1-phenyl-1-ethanol), in various molar ratios, failed to provide the corresponding μ2-alkoxy complex. Instead, pure crystals of {[(CH3)2Sn]2[(CH3)2SnO](OH)(HONZO)(ONZO)} (2a) were isolated.
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