Synthesis of 2-(N-substituted amino)-6-hydroxy-1,2,3,4-tetrahydronaphthalen-1-ol derivatives

DOI: 10.1248/cpb.31.2329

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 2329 - 2348 (1983)

Update date:2022-08-04

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Authors:

Miyake Miyake

Itoh Itoh

Tada Tada

Tanabe Tanabe

Hirata Hirata

Oka Oka

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Article abstract of DOI:10.1248/cpb.31.2329

trans-6-Hydroxy-2-(1-methyl-3-phenylpropyl)amino-1,2,3,4-tetrahydronaphth alen-1-ol (8a), trans-6-hydroxy-2-(1-methyl-2-phenoxyethyl)amino-1,2,3,4-tetrahydronaphtha len-1-ol (8b) and trans-1,6-dihydroxy-2-(1-methyl-3-phenylpropyl)amino-1,2,3,4-tetrahydronap hthalene-5-carboxamide (9a) were synthesized as a part of our search for useful cardiovascular agents. 2-(N-Substituted amino)-6-alkoxy-1,2,3,4-tetrahydronaphthalen-1-ols (10-31) having various substituents at the 5-, 6- and 7-positions of the naphthalene ring were prepared by a five-step sequence of reactions starting from 3,4-dihydro-1(2H)-naphthalenone derivatives (36). Furthermore 2-(N-substituted amino)-1-indanol derivatives (33) and 6-(N-substituted amino)-2-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ols (34, 35) were obtained by the reductive alkylation of the corresponding amino alcohols with carbonyl compounds. These N-substituted amino alcohols (8-35) were tested for vasodilating activity in anesthetized dogs and for β-blocking activity using isolated guinea pig atrial preparations.

Full text of DOI:10.1248/cpb.31.2329

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