Design, synthesis, and structure elucidation of novel 3-aralkyl/arylamino-1-pyridin-3-ylpropenones and 3-adamantyl-5-nicotinoyl-1,2,3,4-tetrahydropyrimidine hybrids with promising anti-inflammatory activities

Abstract

Aiming for the synthesis of unreported molecular hybrids of 1,2,3,4-tetrahydropyrimidine and adamantane moiety containing nicotinoyl group in position 5 of the tetrahydropyrimidine ring suitable for use as anti-inflammatory agents, the precursor enaminones (3a–h) were reacted with 1-adamantanamine (4) and formaldehyde under thermal conditions producing the desired products 5a–h. The enaminone derivatives (3a–h) were obtained by reacting formylated 3-acetylpyrine (2) with various primary amines. The structures of (3-((3s,5s,7s)-adamantan-1-yl)-1-aralkyl/aryl-1,2,3,4-tetrahydropyrimidin-5-yl)(pyridin-3-yl)methanones (5a–h) prepared in this investigation were determined by various analytical and spectroscopic methods, in addition to the X-ray crystallographic analysis. The anti-inflammatory study of the synthesized compounds demonstrated promising activity.