Effect of chiral polyhydrochromenes on cannabinoid system

Enantiomeric Isopulegol as the Chiral Pool in the Total Synthesis of Bioactive Agents

“…At the same time, isopulegol-based derivative 14 f containing a 3bromothiophene substituent inhibits FAAH activity with an IC 50 value of 7.6 μM and thus, it may increase endocannabinoid system activity. [71] Taking into account that FAAH inhibition attenuates various types of pain, it can be assumed that analgesic effect of 14 f found earlier may be caused, at least partly, by FAAH inhibition. [71] Continuing to search for new structural types with analgesic activity, Il'ina et al in 2019 synthesised hydrogenated 2H-chromenes starting from (À )-isopulegol 2 and a number of symmetric aliphatic ketones in the presence of K10 clay as catalyst (Scheme 9).…”

“…[71] Taking into account that FAAH inhibition attenuates various types of pain, it can be assumed that analgesic effect of 14 f found earlier may be caused, at least partly, by FAAH inhibition. [71] Continuing to search for new structural types with analgesic activity, Il'ina et al in 2019 synthesised hydrogenated 2H-chromenes starting from (À )-isopulegol 2 and a number of symmetric aliphatic ketones in the presence of K10 clay as catalyst (Scheme 9). [72] The analgesic activity of heterocyclic compounds was studied in mice using standard models of experimental pain at a dose of 10 mg kg À 1 .…”

“…The effect of octahydrochromanes and their cannabinoid activities was also studied by Li-Zhulanov et al in 2019. [71] Chiral hydrochromenes were synthesised by clay-catalysed reactions of (À )-isopulegol 2 with aromatic and heteroaromatic aldehydes. Polyhydrochromenes containing amino groups were obtained through the interaction of (À )-2 with 5hydroxymethylfurfural, followed by substitution of hydroxy group with bromine and further reaction with amines (Scheme 11).…”