Study On The Optimized Synthesis Conditions Of Flavonolignan5-MHC And Its Drug Resistance

Lots of physiological activity researches showed that flavonolignan5-MHC couldhelp drug active ingredient enter the cell smoothly, was a potent NorA MDR pumpinhibitor and had good synergy auxiliary function for many drugs and excellentbiological activities, so5-MHC was choosed as research target, studying on the totalsynthesis and drug resistance.1. The different synthesis methods and strategies in recent years of flavonolignansand their key intermediates were reviewed.2. The simple and effective total synthesis route of5-MHC was designed. Readilyavailable and inexpensive vanilline as starting materials,3,4-bis-methoxymethoxy-5-methoxybenzaldehyde had been synthesized though bromination, hydrolhydrolysis andhydroxy protection.2-hydroxy-4,6-bis(methoxymethoxy)acetophenone was synthesiz-ed by hydroxy groups selective protected from2,4,6-trihydroxyacetophone, thencondensated by3,4-bis-methoxymethoxy-5-methoxybenzaldehyde with2-hydroxy-4,6-bis(methoxymethoxy)acetophenone in alkaline environment to get chalconederivatives. vanilline as starting materials, with β-dicarbonyl condensation and thenreduction, coniferyl alcohol had been synthesized. The5-MHC was synthesizedthough oxidative cyclization, deprotection and oxidative coupling between chalconeand coni-feryl alcohol.3. The synthesis conditions of intermediates of5-bromovanilline,5-hydroxyvanilline, chalcone derivatives and Flavone derivatives had been optimized. Thevariety bromination conditions of aromatic hydrocarbon derivatives, the effect factorshydroxylation reaction of aromatic hydrocarbon derivatives were discussed. Thesynthesis methods of chalcone were optimized. The preparation methods of flavonoidcompounds in different conditions had been studied.4.1H NMR and13C NMR analysis were used to firm the structures of the target and intermediates.