Electron ionization mass spectral study of oxo- and thio derivatives of minor tobacco alkaloids.

The electron-ionization mass spectra (EI-MS) of oxo- and thio-derivatives of minor tobacco alkaloids and structurally similar piperidine alkaloids, i.e. thiocotinine (1), 2'-oxo-N-methylanabasine (2), 2'-thio-N- methylanabasine (3), 2'-oxoanabasamine (4) and 2'-thioanabasamine (5) are discussed and general fragmentation routes of their molecular cations are proposed. Comparison of the data obtained for 1 with the EI-MS data of metameric metabolites of nicotine: 3'-hydroxycotinine, (A) and 5'-hydroxycotinine, (B) allows a differentiation between these metamers. The data will be useful for the identification of metabolites of alkaloids of these types in biological matrices.

Mass Spectrometry of Bis-Quinolizidine Alkaloids: FAB-MS of Oxo-Substituted Sparteines.

The unpublished in the literature FAB mass spectral fragmentation of seven oxosparteines (i.e., 2-oxosparteine, 15-oxosparteine, 17-oxosparteine, 2,17-dioxosparteine, 2,13-dioxosparteine, 2-oxo-13-hydroxysparteine, and 2-oxo-17-hydroxysparteine) is investigated. Fragmentation pathways, elucidation of which was assisted by FAB/collision-induced dissociation (CID) mass spectra measurements, are discussed. The data obtained create the basis for distinguishing positional isomers.

Thio Analogs of Pyrimidine Bases: Synthesis, Spectroscopic Study, and In Silico Biological Activity Evaluation of New 2-o-(m- and p-)Chlorobenzylthio-6-Methyl-5-Piperidino-(Morpholino-)Methyluracils.

Six new 2-o-(m- and p-)chlorobenzylthio-6-methyl-5-piperidino-(or morpholino-) methyluracils have been prepared. The structures of these compounds were confirmed by spectroscopic (FT-IR, UV-Vis, (1)H NMR, (13)C NMR, and HMBC) and elemental analyses. Estimation of pharmacotherapeutic potential has been made for synthesized compounds on the basis of prediction of activity spectra for substances (PASS).

Electron ionization-induced mass spectral study of 5-methylenecarboxy (5-methylenecarbonylalkoxy)-2-thio-(2-alkoxycarbonylalkylthio)uracils and 3-oxothiazolo-[3,2-a]-pyrimidin-6-methylenecarbonylalkoxy-5-ones.

Electron ionization (EI) mass spectral fragmentation of 2-thio-5-methylenecarboxy (5- methylenecarbonylalkoxy)uracils and their derivatives, five new 2-alkoxycarbonylalkylthio-5-methylenecarboxy (5- methylenecarbonylalkoxy)uracils and three new 3-oxo-thiazolo-[3,2-a]-pyrimidine-6-methylenecarbonylalkoxy-5-ones are investigated. Fragmentation pathways whose elucidation is assisted by accurate mass measurements and metastable transitions are established. The correlations between the abundances of the selected fragment ions and the molecular ions of investigated compounds are discussed. The data obtained create the basis for differentiating structural isomers and can be used for distinction of the compounds investigated from the series of 2- (or 4-) alkoxycarbonylalkylthiouracils, 2-alkoxycarbonylalkylthio-6-carboxyuracils and 1-alkoxycarbonylalkyluracils from their isomers and metamers.

Mass spectrometry of metal complexes of bis-quinolizidine alkaloids: electron ionization and fast atom bombardment mass spectral study of copper(II) (-)-sparteine and (-)-alpha- isosparteine complexes.

The electron ionization (EI) and fast atom bombardment (FAB) mass spectral fragmentations of ten copper(II) dichloride (dibromide, diformate, diacetate and dithiocyanate) complexes of (-)-sparteine and (-)-alpha-isosparteine were investigated. Fragmentation pathways, elucidation of which was assisted by accurate mass measurements and metastable transitions (EI-MS), as well as FAB/collision-induced dissociation (CID) mass spectral measurements are discussed. The data obtained create the basis for the differentiation of the ligand (sparteine or alpha-isosparteine) in the investigated complexes. The comparison of the results with those obtained previously for corresponding zinc(II) complexes forms the basis for the differentiation of metals in these compounds. The results show that both EI-MS and FAB-MS are very useful tools for the differentiation of ligands, as well as metals in the series of Zn(II) and Cu(II) dichloride (dibromide, diacetate, diformate, dithioacetate) complexes of (-)-sparteine and (-)-alpha-isosparteine.

Differentiation of the isomeric o-(m- and p-)nitro-(chloro- and bromo-)benzyl-2,4-(and 2,1-) disubstituted 2-thiocytosinium halides by electron impact ionisation and fast atom bombardment mass spectrometry.

Electron ionisation (EI) and fast atom bombardment (FAB) mass spectral fragmentations of nine 2,4-(and 2,1-) disubstituted o-(m- and p-)nitro-(chloro- and bromo-)-2-thiocytosinium halides are investigated. Fragmentation pathways, whose elucidation is assisted by accurate mass measurements and metastable transitions [EI-mass spectrometry (MS)], as well as FAB/collision-induced dissociation (CID) mass spectra measurements are discussed. The correlations between the abundances of the (C(11)H(10)N(4)SO(2))(+) 1-3; (C(11)H(10)N(3)SCl)(+) 4-6 and (C(11)H(10)N(3)SBr)(+) 7-9 ions and the selected fragment ions (EI- MS), as well as (C(18)H(16)N(5)SO(4))(+) 1-3; (C(18)H(16)N(3)SCl(2))(+) 4-6 and (C(18)H(16)N(3)SBr(2))(+) 7-9 ions and the selected ions (C(7)H(6)NO(2))(+) 1-3; (C(7)H(6)Cl)(+) 4-6; (C(7)H(6)Br)(+) 7-9 (FAB-MS) are discussed. The data obtained can be used for distinguishing isomers.

Synthesis and antimicrobial activity of new (E)-4-[piperidino (4'-methylpiperidino-, morpholino-) N-alkoxy]stilbenes.

The synthesis of twenty-one new (E)-4-[piperidino-(4;-methylpiperidino-, morpholino-)N-alkoxy] stilbenes is reported. The compounds were tested for antimicrobial activities against Gram-negative, Gram-positive bacteria, and fungi. In particular, compounds 3b, 3c, 3f, 3g, 3h, 3k, 3l showed good antibacterial activity against Staphylococcus aureus and 3h, 3k, 3m, 3n also against Bacillus subtilis, as well as 3h, 3n also against Streptococcus faecalis.

Mass spectrometry of bisquinolizidine alkaloids: 2- and 17-cyano-substituted derivatives of sparteine and lupanine.

The mass spectral fragmentations of 2-cyano-2-methylsparteine (1), 2-cyano-2-phenylsparteine (2), 2-cyano-2-(p-tolyl)sparteine (3), 17-cyanosparteine (4) and 17-cyanolupanine (5) were investigated. Fragmentation pathways, whose identification was assisted by accurate mass measurements and a correlation between the abundances of the M(+*) and the selected fragment ions of the investigated compounds, are discussed. The data obtained create the basis for distinguishing the structural metamers.

Antimicrobial activity of some N-alkyl substituted of (E)-4-azachalconium and (E)-3'-hydroxy-4-azachalconium bromides.

Twelve new N-substituted (E)-azachalconium bromides were synthesized and tested for antimicrobial and antifungal activities. Compounds 5c, 5d and 5h-5l showed very good antimicrobial activity against Staphylococcus aureus, Enterococcusfaecalis as well as Bacillus subtilis and 5h-5j showed moderate activity against Escherichia coli. In particular, (E)-N-dodecyl-4-azachalconium bromide (5i) and (E)-N-tetradecyl-4-azachalconium bromide (5j) showed the most intensive activity against all tested microorganisms.