SYNTHESIS OF SCHISTOSOMICIDAL COMPOUNDS: DIALKYLAMINOALKYLAMINO DERIVATIVES OF β-(5-NITRO-2-FURYL)-ACRYLAMIDE

In order to prove the possibility of increasing the schistosomicidal activity, a basic side chain was introduced to nitrofurylacrylamide. The key intermediates of various dialkylaminoalkylamines were prepared by known methods and condensed with β-(5-nitro-2-furyl)-acryloyl chloride to form the corresponding basic amides.In screening with mice infected with Schistosoma japonicum, fifty four out of seventy compounds were found to possess pronounced antischistosomal action. Among these, N-(2-piperidinoethylamino)-β-(5-nitro-2-furyl)acrylamide hydrochloride I₁₃ (F-30385) and its base I₁₄ (F-30642) were shown to be the most effective and tested clinically. The latter compound was shown to have lower adverse reaction with higher therapeutic efficacy than Furapromidium.