ChemInform Abstract: Synthesis and Anthelmintic Activity of a Series of Pyrazino(2,1‐a)(2)benzazepine Derivatives.

Abstract

185ChemInform Abstract The octahydropyrazino(2,1-a)benzazepin-4-one (VI), synthesized from 3-phenyl-1-propylamine (I) as shown in the reaction scheme, is treated with various acyl chlorides such as (VII) to give N-acylated derivatives such as (VIII). Coupling of the N-trityl derivative (X), obtained from (VI) and trityl chloride (IX), with Lawesson's reagent and subsequent detritylation produces the octahydropyrazinobenzazepine-4-thione (XI) which forms the 2-cyclohexanoyl derivative (XII) by acylation with (VIIb). (XII) is also prepared by sulfuration of (VIIIb) with Lawesson's reagent. Reaction of (VI) with methyl cyclohexanecarbodithioate (XIII) yields the cyclohexylthiocarbonyl derivative (XIV). The cestocidal activity of the compounds (VIII), (XII), and (XIV) is evaluated in an in vitro Taenia crassiceps test. The compound (VIIIb) shows the highest activity in this test and in an in vivo test against Taenia pisiformis. Structure-activity relationships are discussed.