Synthesis and photochemistry of new 1,2,3-triazole stilbenes with potential anti-inflammatory activity

Cilj ovog rada bila je sinteza novih 1,2,3-triazolnih stiblena s potencijalnom protuupalnom aktivnosti. Za sintezu triazolnih derivata stilbena korištena je Wittigova reakcija. Općenito se ona koristi za pripravu alkena pri čemu aldehidi ili ketoni reagiraju s fosforovim ilidom. U ovom slučaju korišteni su različiti 1-supstituirani 4-formil-1,2,3-triazoli koji su reakcijom s odgovarajućim fosforovim ilidom dali 1,2,3-triazolne stilbene. Tako dobiveni produkti, zbog konjugirane dvostruke veze koju sadrže, podvrgnuti su fotokemijskim reakcijama. Prilikom osvjetljavanja sintetiziranih derivata došlo je do ciklizacije odnosno zatvaranja prstena. Elektrociklizacijski produkti testirani su na protuupalnu aktivnost. Najbolju protuupalnu aktivnost pokazao je 8-metoksi-1-(3-metoksibenzil)-1H-nafto[1,2-d][1,2,3]triazol čija IC50 vrijednost iznosi 1,9 μM. Što je IC50 vrijednost manja, spoj je aktivniji.The aim of this work was the synthesis of new 1,2,3-triazole stilbenes with potential anti-inflammatory activity. For the synthesis of triazole derivatives of stilbenes Wittig reaction is used. It is generally used to prepare alkenes in which aldehydes or ketones react with phosphorus ylide. In this case, different 1-substitued 4-formyl-1,2,3-triazoles were used, which by reaction with the corresponding phosphorus ylide gave 1,2,3-triazole stilbenes. Products obtained in this way, because of the presence of conjugated double bond they contain, are subjected to photochemical reactions. When illuminating triazole stilbenes cyclization or closure of the ring occurred. Electrocyclization products have been tested for anti-inflammatory activity. The best anti-inflammatory activity was shown by 8-methoxy-1-(3-methoxybenzyl)-1H-nafto[1,2-d][1,2,3]triazole with IC50 value of 1.9 μM. The compound is more active when the IC50 value is lower