Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity.

A number of new octahydro-2H-chromene acetamide derivatives based on the monoterpenoid (−)-isopulegol were synthesized using a one-pot three-component Prins—Ritter reaction. The structure of the target compounds was determined using ¹H and ¹³C NMR spectroscopy, high resolution mass spectrometry, and X-ray diffraction analysis. Most of the products exhibited high analgesic activity in in vivo tests. The highest analgesic activity was found for spirocyclic compound (4S)-2d, the effect of which is apparently mediated through the dopamine system. It was shown that compound (4S)-2d has a low acute toxicity. [ABSTRACT FROM AUTHOR]