The syntheses and biological activities of o-aminophenylalanine and related compounds

The general conditions and results of rearrangement studies of the 5‐, 6‐, 7‐, and 8‐chloro‐substituted 3‐amino‐3,4‐dihydro‐1‐hydroxycarbostyrils in concentrated hydrochloric and hydro‐bromic acids to the corresponding dihalosubstituted 3‐amino‐3,4‐dihydrocarbostyrils have been described. The 5‐, 7‐ and 8‐chlorocarbostyrilhydroxamic acids undergo nucleophilic displacement by either chloride or bromide ion preferentially at the 6‐position to form the respective 5,6‐, 6,7‐ and 6,8‐dihalolactams. However, with the 3‐amino‐6‐chloro‐3,4‐dihydro‐1‐hydroxycarbo‐styril where the 6‐position is blocked, nucleophilic displacement by halide ions occurs at the 8‐position to afford the 6,8‐dihalolactams. The 6,8‐dichloro‐ and 6,8‐dibromolactams were also prepared by alternative halogenation procedures for purposes of comparison with the rearrangement products.

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Benzolactams. A new class of converting enzyme inhibitors

Parsons

Davidson

Taub

et al. 1983

Biochemical and Biophysical Research Communications

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The syntheses and biological activities of o-aminophenylalanine and related compounds

Cited by 4 publications

References 6 publications

The rearrangement of 3‐amino‐3,4‐dihydro‐1‐hydroxycarbostyril to 3‐amino‐3,4‐dihydro‐6‐hydroxyearbostyril

The rearrangement of 3‐amino‐3,4‐dihydro‐1‐hydroxycarbostyril to 3‐amino‐3,4‐dihydro‐6‐hydroxyearbostyril

Rearrangement of some chlorosubstituted 3‐amino‐3,4‐dihydro‐1‐hydroxycarbostyrils in hydrogen halide acids

Benzolactams. A new class of converting enzyme inhibitors

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