2014

Yeni Azakalkon-Şeker Hibrit Bileşiklerinin Sentezi

Doğada bulunan ve bitkilerin sentezledikleri biyoaktif bileşiklerin pek çoğu flavonoid türü bileşiklerdir. Flavonoid ailesinin önemli üyelerinden olan kalkon sınıfı bileşikler ve bunların alternatif türevleri olan azakalkon bileşikleri sahip oldukları geniş biyolojik, farmakolojik (antibakteriyal, sitotoksik, antimalaryal, enzim inhibisyonu, antitüberklostatik, antioksidan vb.) ve boya özelliklerinden ötürü son yılların ilgi odağı haline gelmişlerdir. Diğer taraftan karbohidrat bileşiklerinin biyolojik sistemlerde bağışıklık sistemi, iltihap oluşumu, hücre büyümesi ve adezyon üzerine etkileri bilinmektedir. Şekerlerin heterosikliklerle bir araya geldiği glikohibrit bileşikler ise antikanser ve antitümör ilaçlarında önemli etkiye sahiptirler ve enzim aktivitesinin inhibisyonunda iyi bir glikozil verici olarak davranmaktadırlar. Bu çalışmada amino sübstitüe azakalkon bileşiklerinden (1-3) N-β-D-glikopiranosit (4-6) ve N-glikozidik 2,3,4,6-tetra-O-asetil-β-D-glikopiranosit (7-9) türevlerinin sentezi gerçekleştirilmiştir.

Anahtar Kelimeler:

Azakalkon, β-Anomer, Glikohibrit, N-Glikozidik bağ

Synthesis of Novel Azachalcone-Sugar Hybrid Compounds

Many of the bioactive compounds found in nature and synthesized by plants are flavonoid-type compounds. Chalcones and their alternative derivatives azachalcones, which are important members of the flavonoid family, have become the focus of attention in recent years due to their wide range of biological, pharmacological (antibacterial, cytotoxic, antimalarial, enzyme inhibition, antitubercostatic, antioxidant etc.) and dye properties. On the other hand, it is known that carbohydrate compounds in biological systems have effects on inflammation, immune responses, cell growth, and adhesion. Glycohybrid heterocyclic compounds, a heterocyclic and sugar combination, have significant effect in anticancer and antitumor drugs, and behave as a good glycosyl donor on the inhibition of enzyme activity. In this study, synthesis of N-β-D-glucopyranoside (4-6) and N-glycosidic 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7-9) derivatives were performed via amino substituted azachalcones.

Keywords:

Azachalcone, β-Anomer, Glycohybrid, N-Glycosidic bond,

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