Synthetic experiments in the benzopyrone series. Part IX. Partial demethylation of chalkones: a synthesis of sakuranetin

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Synthetic experiments in the benzopyrone series. Part XXVII. A note on the synthesis of santal

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A new effect of hydrogen bond formation (chelation) Part VI. Synthesis of 5-hydroxy-2'-methoxy flavanone and 5:7-dihydroxy-2'-methoxy flavanone

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A new effect of hydrogen bond formation (chelation) Part IV. Abnormal behaviour of 2'-hydroxy flavanones

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A New Class of Monoamine Oxidase Inhibitors

Newly synthesized compounds have been found to inhibit mitochondrial monoamine oxidase (MAO) in mouse brain and rat liver. A series of 2-acylamino-3- tert -aminopropiophenones acted preferentially against MAO type B (2-phenylethylamine as substrate), apparently irreversibly. 2-Decanoylamino-3-morpholinopropiophenone acted similarly in vivo toward the cerebral MAO, producing a dose-related inhibition. At high dose levels, MAO type A was also severely inhibited. The effects were produced rapidly and restoration of enzyme activity also appeared rapidly. The half-life for MAO type A could be estimated from the rate of enzyme reappearance to be 13 h. It is suggested that the amino ketones undergo a Β-elimination reaction at the enzyme's active site, forming a reactive species (an Α,Β-unsaturated ketone), which reacts covalently with a nucleophilic group of the enzyme by a Michael addition. Some other related compounds, derivatives of phenylpropane, also showed inhibitory activity against MAO, particularly against type A (serotonin as substrate). The morpholino compound might have promise as a quickly effective, short-acting inhibitor of MAO type B.Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/66333/1/j.1471-4159.1980.tb06611.x.pd

Synthetic experiments in the benzopyrone series. Part XLII. A new synthesis of 5:6: 7-trihydroxy isoflavone derivatives

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Nuclear oxidation in flavones and related compounds. Part XXXVI. Oxidation of some hydroxy isoflavones

Using methods of nuclear oxidation 7 : 8-dihydroxy-2-methyl isoflavone, 5 : 7 : 8-trihydroxyisoflavone and 5 : 7 : 8-trihydroxy-2-methyl isoflavone and their derivatives have been prepared. Demethylation of the 5 : 7 : 8-trimethoxy isoflavones with or without a 2-methyl group does not produce isomeric change in the trihydroxy product. It could therefore be concluded that a phenyl group in the 3-position prevents this isomeric change just like a methoxyl (hydroxyl) in the same position and that substitution in the 2-position has no influence

Synthetic experiments in the benzopyrone series. Part X. Synthesis of carthamidin and iso-carthamidin

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