27148-03-4Relevant academic research and scientific papers
Zn thiosacharinates: From ionic to polymeric structures. Synthesis, characterization and cell proliferation inhibition studies
Delgado, Fermín,Freire, Eleonora,Baggio, Ricardo,González Pardo, Verónica,Dorn, Viviana,Dennehy, Mariana
, p. 266 - 274 (2018)
A series of Zn thiosacharinates complexes with nitrogen donor co-ligands were synthesized: [Zn(tsac)2(o-phen)], [Zn(tsac)2(TMDP)]n, [(4,4′-bipy)H2][Zn(tsac)4] [Zn(tsac)2(2,2′-bipy)], [Zn(tsac)2(2,2′-bquin)], (tsac, thiosaccharinate anion: 1,1-dioxo-1,2-benzisothiazole-3-thiolato, C7H4NO2S2?, o-phen: 1,10′-phenantroline, TMDP: trimethylenedipyridine, 2,2′-bipy: 2,2′-bipyridine, 4,4′-bipy: 4,4′-bipyridine, 2,2′-bquin: 2,2′-biquinoline). They were fully characterized by means of FTIR, 13C and 1H NMR, elemental analysis and conductivity measurements. Three of them, [Zn(tsac)2(o-phen)], [(4,4′-bipy)H2][Zn(tsac)4], [Zn(tsac)2(TMDP)]n were also characterized by X-ray single crystal diffractometry and their crystal structures are described herein. DFT geometry optimization for the [Zn(tsac)2(o-phen)] complex was performed and its vibrational spectra was predicted. Moreover, we studied the effects of the five complexes on cell proliferation, thus providing preliminary evidence for their therapeutic potential as anti-cancer drugs.
A new supramolecular assembly obtained by reaction between thiosaccharin and hexamethylenediamine
Baran, Enrique J.,Piro, Oscar E.,Zinczuk, Juan
, p. 1530 - 1534 (2007)
The crystal structure of hexamethylenediammonium bis(thiosaccharinate) dihydrate, [H3N-(CH2)6-NH3](tsac) 2 · 2 H2O (tsac = C7H4NO 2S2, the anion of thiosaccharin), was determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group P21/a with Z = 4. The thiosaccharinate moiety is planar and shows small but significant modifications in the bonding of the thioamide functional group as compared with the protonated neutral molecule. The ionic crystal is further stabilized by an extensive H-bonding network, which links the anions and cations into an infinite three-dimensional supramolecular assembly. The FTIR spectrum of the compound is briefly discussed in comparison with those of the neutral constituent molecules.
Structural study of thiosaccharin by single crystal X-ray diffraction and infrared spectroscopy
Grupce, O.,Penavic, M.,Jovanovski, G.
, p. 581 - 586 (1994)
The structure of thiosaccharin (1,2-benzisothiazol-3(2H)-thione 1,1-dioxide) has been investigated by X-ray diffraction and infrared spectroscopic methods.The compound crystallizes in the orthorhombic space group Fdd2 with a = 26.591(3), b = 25.058(3), c = 4.934(5) Angstroem, Z = 16.The structure consists of thiosaccharin molecules bonded to each other through N-HO intermolecular hydrogen bonds.The infrared spectra of the thiosaccharin at room and liquid-nitrogen temperature were recorded.The spectral features in the N-H stretching region were correlated with the crystallographic data on the geometry of the N-HO hydrogen bonding.In an attempt to assign the bands due to the SO2 stretching modes, the spectrum of thiosaccharin was compared with that of saccharin (1,2-benzoisothiazole-3(2H)-one, 1,1-dioxide.KEY WORDS: Thiosaccharin, infrared spectra, crystal structure polymorphs.
A new supramolecular assembly obtained by reaction between thiosaccharin and pyridine
Piro, Oscar E.,Zinczuk, Juan,Baran, Enrique J.
experimental part, p. 877 - 879 (2009/03/11)
The crystal structure of pyridinium thiosaccharinate thiosaccharin, [HNC5H5]+ [(tsac)(Htsac)]- (Htsac = C7H5NO2S2, the thiosaccharin molecule), was determined by single-crystal X-ray diffraction. Both, the thiosaccharinate anion, the corresponding neutral molecule and the pyridinium cation are nearly planar and arranged in the solid state in an almost parallel fashion, hence giving rise to a layered supramolecular structure. The anion shows small but significant modifications in the bonding of the thioamide group as compared with the neutral molecule. The crystal is further stabilized by an extensive H-bonding network. The FTIR spectrum of the compound is briefly commented.
Pseudosaccharin amine derivatives: Synthesis and elastase inhibitory activity
Rode, Haridas B.,Sprang,Besch,Loose,Otto, Hans-Hartwig
, p. 723 - 731 (2007/10/03)
Pseudosaccharin amines were synthesized from saccharin either by the reaction of pseudosaccharin chloride with amines, or via thiosaccharin which was treated with amines yielding thiosaccharinates, and their reaction with glacial acetic acid. This route gave lower yields than the first way. The synthesis of alkyl [(1,1-dioxo-benzo[d]isothiazol-3-yl)amino]alkanoates as possible Human Leukocyte Elastase (HLE) inhibitors was realized by the reaction between amino acid esters and pseudosaccharin chloride. Hydrolysis of the esters was possible under aqueous basic conditions. Selected compounds were screened for elastase inhibitory activity. Compounds 4k and 4m were found to be reversible inhibitors of HLE with Ki values of 45 μM and 60 μM.
