Synthesis of amides of 2-(3,3,7-trimethyl-3,4-dihydroisoquinolyl-1)ethanoic acid and their effects on arterial blood pressure

Abstract

The reaction of 2-methyl-1-(p-tolyl)propanol-2 with N-alkyl-, N-benzyl-, and N-arylcyanacetamides was used to synthesize 2-(3,3,7-trimethyl-3,4-dihydroisoquinolyl-1)ethanoic acid amides. Investigations showed that tertiary amides formed from cyclic amines (morpholine, piperidine, etc.) had hypertensive actions, while all the other amides had hypotensive effects). The most active compound decreased arterial pressure by 46 mmHg and the duration of action was 90 min.

Thiocarbamoylation of 1,2,3,4-tetrahydroisoquinoline enamines with phenyl isothiocyanate

“…The strongly downfield position of the latter signal indicates formation of H-chelate ring which stabilizes the Z configuration. It should be noted that this signal is located in a weaker field (by 2.5-3 ppm) than the corresponding signal of amides [3,5,14], which may be due to higher polarizability of the sulfur atom.…”

“…Enamino ketones [1], enamino esters [2], enamino amides [3][4][5], and enamino nitriles [6] derived from 1,2,3,4-tetrahydroisoquinoline have been studied previously. Reactions of these compounds with isothiocyanates have been studied poorly.…”