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Synthesis of 11-Phenyl-2, 3, 4, 5-tetrahydro-1 H-(1, 4)diazepino(1, 2-a)indoles and 1-(3-Aminopropyl)-2-hydroxymethyl-3-phenylindoles as 5-Hydroxytryptamine Antagonists

1990; Elsevier BV; Volume: 79; Issue: 2 Linguagem: Inglês

10.1002/jps.2600790218

1520-6017

Sharanabasava B. Rajur, A. Y. MERWADE, L. D. Basanagoudar,

Phenothiazines and Benzothiazines Synthesis and Activities

A series of novel 11-phenyl-2, 3, 4, 5-tetrahydro-1H-(1, 4)diazepino(1, 2-a)indoles (5a–f) and 1-(3-aminopropyl)-2-hydroxymethyl-3-phenylindoles (6a–f) are reported. The compounds (5a–f) were prepared by the lithium aluminum hydride (LAH) reduction of corresponding 11-phenyl-1H-1-oxo-2, 3, 4, 5-tetrahydro(1, 4)diazepino(1, 2-a)indoles (4a–f). The precursors (4a–f) were, in turn, prepared by the catalytic reduction of 1-(2-cyanpethyl)-3-phenylindole-2-carboxylates (2a–f) and cyclization of the resulting 1-(3-aminopropyl)-3-phenylindole-2-carboxylates (3a–f) with sodium hydride in xylene. The LAH reduction of 2a–f gave exclusively 1-(3-aminopropyl)-2-hydroxymethyl-3-phenylindoles (6a–f) and not the diazepinoindoles (5a–f) which were expected. The title compounds and the intermediates have been screened for their anti-5-hydroxytryptamine (anti-5-HT) activity. The most potent anti-5-HT compounds of this series, 6a and 6e, were found to be weak compared with cyproheptadiene, a standard anti-5-HT drug.