Trihalogenomethyl compounds of potential therapeutic interest. Part VII. Some selective reductions

Bishop, D. C.; Williamson, W. R. N.

doi:10.1039/j39670001827

Cited by 2 publications

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“…(E) -4,4,4-Trichlovobut-2-en-1 -oZ ( 7) .-Ethyl 4,4,4-trichlorobutenoate (10.85 g) was dissolved in dry ether (160 ml). A slurry of lithium aluminium hydride (0.38 g) and aluminium trichloride (13.3 g) in ether was added with cooling and vigorous stirring during 0.5 h, the temperature being maintained between 15 and 20 "C. After the addition was complete, stirring was continued for 0.5 h and then aqueous methanol (50%, 20 ml) was added during 0.5 h followed by 6~ sulphuric acid (50 nil).…”

Section: Ex Per1 M E N Talmentioning

confidence: 99%

Latent inhibitors. Part 2. Allylic inhibitors of alcohol dehydrogenase

MacInnes¹,

Schorstein²,

Suckling³

et al. 1981

J. Chem. Soc., Perkin Trans. 1

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The syntheses of a number of 3-substituted prop-2-en-l -ols and -1 -als, required for studying the latent inhibition of horse liver alcohol dehydrogenase (E.C. 1.1.1 .I ), are described. Substituents were chosen to cover a range of alkoxide, phenolate, thiolate, and halide leaving groups. Of the compounds studied, only 3-ethylthioprop-2-en-l-01 proved to be a latent inhibitor through oxidation to the corresponding aldehyde, catalysed by the enzyme. The persistence of inhibition caused by this inhibitor is shown, by product studies and kinetic measurements, to be due to ethanethiol, formed by an enzyme-catalysed hydrolysis of the aldehyde. TABLE 1 Inhibition properties of the compounds studied a Krn IM Kl I M Inhibition propcrties Competitive, b slow inactivation 1.54 x 10-4 1.25 x lea 6.4 x 10-4 5.0 x los6 1 . 3 x 10-6 5.2 x 1 0 -4 Perkin I Competitive; no time-dependent inactiva-Neither substrate nor inhibitor No time-dependent inactivation tion, forms malonic dialdehyde No time-dependent inactivation Competitive, no time-dependent inactiva-Rapid covalent inhibition at 1 0 -s ~, 4 = 2 tion, forms malonic dialdehyde min Rapid covalent inhibition at 1 0 -6 ~, ti = 30s No time-dependent inactivation Competitive, reversible No time-dcycndciit inactivation 6.2 x lo-' Competitive, reversible Compounds were assayed at pH 9 in the presence of NAL) (1.5 x l P 3 ~) , using 3.76 x l0-'-1.5 x 1 W 6 ~ lIL.4DH. Q ' Conipetitive refers to competition with ethanol.[0/1182 Received, 28th JuZy, 108OJ

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Section: Ex Per1 M E N Talmentioning

confidence: 99%

Latent inhibitors. Part 2. Allylic inhibitors of alcohol dehydrogenase

MacInnes¹,

Schorstein²,

Suckling³

et al. 1981

J. Chem. Soc., Perkin Trans. 1

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“…Bishop und Williamson [9] haben die Darstellung von 2 b X = OH durch Reduktion des y,y,yTrichlorcrotonsäuremethylesters beschrieben, jedoch sprechen die IR-Daten nach Le Coq [6] eher dafür, daß das Produkt 7 a ist. ClaC-CHa-CHBr-CHa-O-Ts…”

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Die Synthese von 1-substituierten 4.4.4-Trichlor-Δ² -trans-butenen / The Synthesis of 1-Substituted 4,4,4-Trichloro-Δ² -trans-butenes

Seidel

Ugi

1982

Zeitschrift Für Naturforschung B

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Trihalogenomethyl compounds of potential therapeutic interest. Part VII. Some selective reductions

Abstract: The ester groups in methyl 3-trichloromethylacrylate and ethyl trichloromethylglycidate have been selectively reduced to the corresponding primary alcohols.

Cited by 2 publications

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Latent inhibitors. Part 2. Allylic inhibitors of alcohol dehydrogenase

Latent inhibitors. Part 2. Allylic inhibitors of alcohol dehydrogenase

Die Synthese von 1-substituierten 4.4.4-Trichlor-Δ² -trans-butenen / The Synthesis of 1-Substituted 4,4,4-Trichloro-Δ² -trans-butenes

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Trihalogenomethyl compounds of potential therapeutic interest. Part VII. Some selective reductions

Abstract: The ester groups in methyl 3-trichloromethylacrylate and ethyl trichloromethylglycidate have been selectively reduced to the corresponding primary alcohols.

Cited by 2 publications

References 0 publications

Latent inhibitors. Part 2. Allylic inhibitors of alcohol dehydrogenase

Latent inhibitors. Part 2. Allylic inhibitors of alcohol dehydrogenase

Die Synthese von 1-substituierten 4.4.4-Trichlor-Δ2 -trans-butenen / The Synthesis of 1-Substituted 4,4,4-Trichloro-Δ2 -trans-butenes

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Die Synthese von 1-substituierten 4.4.4-Trichlor-Δ² -trans-butenen / The Synthesis of 1-Substituted 4,4,4-Trichloro-Δ² -trans-butenes