Synthesis of 2-(N-substituted amino)-6-hydroxy-1,2,3,4-tetrahydronaphthalen-1-ol derivatives.
Year: 1983
Type: article
Abstract: trans-6-Hydroxy-2-(1-methyl-3-phenylpropyl) amino-1, 2, 3, 4-tetrahydronaphthalen-1-ol (8a), trans-6-hydroxy-2-(1-methyl-2-phenoxyethyl) amino-1, 2, 3, 4-tetrahydronaphthalen-1-ol (8b) and trans-1, 6-dihydroxy-2-(1-methyl-3-phenylpropyl) amino-1, 2, 3, 4-tetrahydronaphthalene-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.
DOI: 10.1248/cpb.31.2329
Authors: AKIO MIYAKE, KATSUMI ITOH, NORIO TADA, MASAO TANABE, MINORU HIRATA, YOSHIKAZU OKA
Institution: Takeda (Japan)
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W1521312907