2-Amino-3-acyl-1,4-naphthoquinones

Amino-substituted naphthoquinones and heterocyclic variants have been disclosed in the patent literature as 5-LO inhibitors. Compounds represented by (80) (X = C, N) from Lilly inhibited SRS-A release from sensitized guinea-pig lung tissue [218]. Similar compounds such as (81) (R = carboxylic ester, acyl, or aryl) and related naphthalene derivatives, from American Cyanamid, gave good inhibition in guinea-pig ISN (at 10 //g/ml) and in passive cutaneous anaphylaxis in mice (25-60 /zM i.p.) [219,220]. 

Alternative intramolecular hydrogen abstractions are possible in a, 3-unsaturated carbonyl compounds. Irradiation of the 2-(N-acyl-N-alkyl-amino)cyclohex-2-enones (115), for example, gave the lV-alkyl-1-azaspiro[3.5]nonane-2,5-diones (116), presumably via 1,4-biradical intermediates (117), The 2-(dialkylamino)-3-acetylenyl-1,4-naphthoquinones... 

Amino-3-acyl-l,4-naphthoquinones. The redox transformation of 2-azido-3-alkenyl-1,4-naphthoquinones by PhjP is quite unexpected (4 examples, 45-60%). ... 

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