Thioether Compounds Research Articles

Studies of the inhibition of dopamine β hydroxylase by thiono-sulfur containing compounds

The inhibitory effect of several thione and thioether compounds on dopamine β hydroxylase has been examined. Carbon disulfide and propylthioracil inhibited the enzyme competitively and showed a Ki of 1.1 × 10 −4 and 1.0 × 10 −4M, respectively. Dialysis reversed the inhibition but N-ethylmaleimide did not. The thioethers methionine, benzylmethyl sulfide, thiazole and 2-amino-thiazole had no inhibotory effect on enzymatic activity. No evidence of oxidative metabolism of the thione inhibitors by dopamine β hydroxylase could be detected.

Copolymerization of Butadiene and Styrene with n-Butyllithium-Polar Organic Compound Mixture and n-Butyllithium-Alkaline Metal Complex

Copolymerizations of butadiene and styrene were investigated with n-buthllithium (BuLi)polar organic compound mixture and BuLi-alkaline metal complexes which were used as catalyst at 40°C or 50°C in n-hexane. The weight ratio of butadiene to styrene was 75: 25 and that of the monomer to solvent was 1: 4 in all cases.The polar organic compounds used were classified as follows: i) ether compounds, ii) acetallike compounds, iii) tertiary amine compouns, iv) thioether compounds and v) hetero ring compounds. When the styrene content of copolymers obtained by initiating with BuLi and polar organic compounds of group i), ii) or iii) and by terminating at 20∼60% conversion, was correlated with 1, 2-addition content of butadiene units, a fairly good linear relationship was observed among 24 compounds. While, an addition of any compound similar to thioether or hetero ring compounds to BuLi exhibited little or no effect on both the polymerization rate and the course of copolymerization.It was found that the complexes obtained by the reaction of BuLi with alkaline metals(except Na) in aromatic solvent gave random copolymers of butadiene and styrene. Copolymerizations were carried out by using the following combined catalysts with various mole ratio to BuLi: (a) BuLi-K complex, (b) BuLi-tetrahydrofuran (or diethylether) and (c) BuLi-o-dimethoxybenzene. A good linear relationship was also observed between 1, 2-addition content and styrene content of copolymers obtained, whose slopes were in the order: (a)>>(b) (cf. Fig.2).The styrene sequence distribution for a random copolymer obtained by (a) was discussed on the basis of NMR and far-infrared spectroscopic measurements. The molecular weight distribution of this copolymer was measured by gel-permeation chromatography.

Synthesis of the furan derivatives. XLIX. Wittig reaction of organosulfurphosphoranes with some aromatic aldehydes

Wittig reaction was carried out under usual reaction conditions on sulfur-containing complex ylides, α-(para-substituted phenylthio)ethoxycarbonyl-(III), -cyano-(V), -benzoyl-(VII), and-furoylmethylenetriphenylphosphoranes (IX), with 5-nitro-2-furfural (XI). It was found that, of these complex ylides, IIIa-d and Va-d afforded the corresponding vinyl thioethers. With IIIa-d, reaction was carried out on p-nitrobenzaldehyde (XVIII) and 5-nitro-2-thiophenecarboxaldehyde (XXIII), and the corresponding vinyl thioether compounds were obtained. Each of these thioethers was separated into two kinds of stereoisomers, and their steric configuration was determined from their IR and NMR spectra. The vinyl thioethers were oxidized with hydrogen peroxide to the corresponding vinyl sulfones.

Fluorometric estimation of GSH-OPT

Cohn and Lyle (1) have reported that under certain conditions reduced glutathione (GSH) and o-phthalaldehyde (OPT) react to produce a highly fluorescent compound, and that no other compound tested, including GSSG and 16 other sulfhydryl, disulfide, or thioether compounds, yields fluorescence with OPT under those conditions. They have also described (2) a procedure whereby this reaction may be used to determine GSH content of liver and blood samples. Described here are experiments carried out to examine in some detail the GSH-OPT reaction and to confirm the usefulness of Cohn and Lyle's method. It was found in this laboratory that some material present in both HClO 4 and HPO 3 extracts of whole blood, washed erythrocytes, and liver from rats and mice, and of washed erythrocytes from humans, gave appreciable quenching of fluorescence developed by OPT. It was also found that the concomitant error in the tissue GSH content indicated by such quenched fluorescence could be minimized or eliminated by diluting the tissue extracts in the reaction mixtures 75,000 times for liver or 15,000 times for erythrocytes, at which point the quenching was no longer evident. At such dilutions it was found necessary to use a special attachment on the fluorometer employed in this laboratory to attain sensitivity sufficient to allow reliable measurement of the low levels of fluorescence resulting from the dilutions. Under these circumstances satisfactory results could be achieved.

含硫黄ピリミジン誘導体の研究 (第3報)

The properties of the alicyclic portion of a new fused heterocyclic compound, 7-methyl-4H-pyrimido [4, 5-d]-m-thiazin-2(1H)-one (I) was examined. Application of lithium aluminum hydride results in the reduction of carbonyl to methylene and not cleavage of the ring. Oxidation with hydrogen peroxide in glacial acetic acid results in the formation of 2-methyl-4-amino-5-pyrimidinylmethanesulfonic acid (XII) and not pyrimidine N-oxide. Heating with alkali hydroxide effects decarboxylation to form 2-methyl-4-amino-5-pyrimidinylmethanethiol hydrochloride (XV).The previously reported disulfide compound (III) and the isothiuronium hydrogen carbonate (IV) also form sulfonic acid compound (XII) on oxidation with hydrogen peroxide in glacial acetic acid, while the thioether compound (VI) is oxidized first to a sulfone (VII) and then the pyrimidine ring is cleaved to form acetylurea.

細菌によるthioether化合物の分解に關する研究Methylmercaptan形成に就て (第1報)

細菌によるthioether化合物の分解に關する研究Methylmercaptan形成に就て (第1報)

49. The structure of the thio-ether compounds of platinous and palladous chlorides

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