Potenciálisan biológiailag aktív pterokarpán származékok előállítása

Abstract

A Debreceni Egyetem Szerves Kémiai Tanszékén az O-heterociklusos vegyületek körében folyó kutatásokhoz kapcsolódva doktori munkám célja az Ipriflavonnal (8a) rokonszerkezetű potenciálisan csontritkulás ellenes hatású pterokarpánok és rokon vegyületeik szintézise, valamint sztereokémiai vizsgálata volt. A pterokarpánok enantioszelektív szintézise kapcsán pedig a flavanon gyűrűszűkülését részleteiben is tanulmányoztuk. Flavonoids are one of the largest and the most important group of naturally occurring O-heterocycles. According to the more general terminology, O-heterocyclic natural products possessing a diphenylpropane skeleton (C6-C3-C6) and their related open chain derivatives are considered to belong to this family of organic compounds. In the past few decades, numerous and diverse pharmacological investigations were carried out which confirmed that flavonoids possess antibacterial, antiviral, antifungal, antiinflammatory, diuretic, anti-tumor and antiosteoporotic activity above their well-known antioxidant activity. The aim of my dissertation was to synthetise 7-isopropyloxyisoflavone [Ipriflavone (8a)]’s analogues, such as pterocarpan (1b) and its related derivatives (1c,d) of potential antiosteoporotic activity in racemic and optically pure form and to study their stereochemistry. In relation to the enantioselective synthesis of pterocarpans, we studied the ring contraction of flavanone in details.