Synthesis and analgesic activity of new heterocyclic compounds derived from monoterpenoids

Prins cyclization: Synthesis of compounds with tetrahydropyran moiety over heterogeneous catalysts

“…It has been discovered that compounds with 6-membered oxygen-containing heterocycles with tetrahydropyran moiety are widely used for the synthesis of biologically active compounds with a potential for use in medicine [1]. These compounds can exhibit analgesic, anti-inflammatory or cytotoxic activity [1][2][3][4]. Synthesis of compounds with the desired tetrohydropyran structure can be realized by several important methods, including Prins cyclization onto oxocarbenium ions, oxy-Michael reactions, transition metal catalyzed cyclizations, reduction of cyclic hemi ketals and hetero-Diels-Alder cycloaddition [1].…”

A practical way to synthesize chiral fluoro-containing polyhydro-2H-chromenes from monoterpenoids

“…Previously, using the aldehyde as a reactant in a reaction with diol 1 catalyzed by K10 montmorillonite clay led to a sharp decrease in the yield of product 2e [2]. In our case, the yields of products containing a fluorine atom ( 8e ) and a hydroxy group ( 2e ) were 42% and 35%, respectively (Table 2).…”

“…Products of these reactions are of interest as many of them exhibit a significant analgesic activity in vivo [2–4]. …”

Formation of epoxychromeno[4,3-c]isoquinolines through diastereoselective one-pot IMDA reaction of 4-chloro-3-[(1E)-3-oxo-3-phenyl-1-propen-1-yl]-2H-chromen-2-one and furfurylamine

“…Among all these methods, few reports have been addressed about epoxychromenes due to their complex structure. Mikhalchenko group studied new bicyclic chromenes and investigated their analgesic activity [13].…”