A synthetic route to C(4/5)-bis(phosphinoyl)imidazole-2-thiones (7d,e) (d: R(1) = (n)Bu, R(2) = Me; e: R(1) = n-dodecyl, R(2) = Me) and C(4/5)-bis(thio/selenophosphinoyl)imidazole-2-thiones (8b,c), (9a,b,e) and 10a (a: R(1) = R(2) = Me; b: R(1) = R(2) = Ph, c: R(1) = (i)Pr, R(2) = Me) is presented that employs initial C(5) lithiation of mono-phosphinoyl/thiophosphinoyl substituted imidazole-2-t...

Two small cell lung cancer (SCLC) cell lines were established from pericardial and pleural effusions of a patient with histopathologically proven SCLC of the oat cell type. Chemotherapy was administered without response during the 148-day period prior to the establishment of the first cell line, SCLC-22H, and some of the same drugs were administered in the 15 days prior to the establishment of ...

Non-fused 3,6-dihydro-2H-1,3-thiazine-2-thiones constitute a so far rather unexplored class of compounds, with the latest report dating back more than two decades. Thiazine-2-thiones contain an endocyclic dithiocarbamate group, which is often found in pesticides, in substrates for radical chemistry and in synthetic intermediates towards thioureas and amidines. We now report the multicomponent r...

The catalysis by S, 1 0, IS,20-tetrakis(pentafluorophenyl)-21H,23H-porphyrin iron(III) chloride (F20 TPPFeCl) of alkene epoxidation by H20 2 has been investigated. Extensive catalyst decomposition was observed during the reaction. A kinetics and product yield analysis has shown that this decomposition does not occur via either the oxoperferryl intermediate (F 20 TPP·+)F e =0 or the oxoferryl in...

Driven by the shortage of known effective possibilities for the synthesis of 4-hydroxy-3,4-dihydro-2H-1,3-thiazine-2-thiones on the one hand and the promising potential of these structures as novel drug candidates on the other hand, synthetic access to 4-hydroxy-3,4-dihydro-2H-1,3-thiazine-2-thiones was developed. The desired products could be synthesized effectively and facilely starting from ...

We have developed a liquid-phase route for combinatorial synthesis of novel substituted 5-(1,2,4-oxadiazol-5-yl)-3,4-dihydropyrimidine-2(1H)-thiones. Biginelli-type three-component condensation of 1-(3-aryl-1,2,4-oxadiazol-5-yl)acetones, thiourea, and benzaldehydes is shown to result in new 5-(1,2,4-oxadiazol-5-yl)-3,4-dihydropyrimidine-2(1H)-thione heterocyclic system. If salicylaldehydes are ...

We report the unexpected formation of a 1-azadiene dimer from 4,6-diphenyl-3,6-dihydro-2H-1,3-thiazine-2-thiones under prolonged microwave irradiation. In this manner, thiazine-2-thiones act as "masked" 1-azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed dias...

Mammalian flavin-containing monooxygenase (FMO) is active towards many drugs with a heteroatom having the properties of a soft nucleophile. Thiocarbamides and thiones are S-oxygenated to the sulfenic acid which can either react with glutathione and initiate a redox-cycle or be oxygenated a second time to the unstable sulfinic acid. In this study, we utilized LC-MS/MS to demonstrate that the oxy...

New 5-(2-thienyl)-1,2,4-triazoles and 5-(2-thienyl)-1,3,4-oxadiazoles namely, N-[3-mercapto-5-(2-thienyl)-1,2,4-triazol-4-yl]-N'-arylthioureas 4a-e, 2-arylamino-5-(2-thienyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 5a-e, 3-arylaminomethyl-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 7a-e, 3-(N-substituted anilinomethyl)-5-(2-thienyl)-1,3,4-oxadiazoline-2-thiones 8a, b and 3-(4-substituted-1-pipe...

1,2-Dithiole-3-thiones are an important class of anticarcinogens that selectively induce cellular production of chemoprotective phase II detoxification enzymes. It is important to identify chemical properties of anticarcinogens that are responsible for this enzyme induction. Previously, the ability of 1,2-dithiole-3-thiones to induce phase II enzymes has been attributed to their electrophilic c...