Hulya AKINCIOGLU, Baris ANIL, Halise Inci GUL, Mehtap TUGRAK

Piperonal Artığı Taşıyan Şalkonların Dizaynı, Sentezi ve Biyolojik Aktiviteleri

Heterosiklik bileşikler, farmakolojik olarak aktif bileşikler arasında özel bir öneme sahiptir. Bu çalışmada, bazı piperonal bazlı şalkonlar (PC1-PC10), 3,4-metilendioksibenzaldehid ve birkaç asetofenon arasında Claisen-Schmidt Kondenzasyonu ile sentezlendi. Şalkonların inhibisyon potansiyelleri insan karbonik anhidraz I, II enzimlerine (hCA I ve hCA II) ve asetilkolinesteraz (AChE) enzimine karşı araştırıldı. Şalkon türevlerinin, hCA I için 5.11-109.70 μM, hCA II için 17.05-162.59 μM ve AChE için 18.52-98.69 μM aralığında IC50 değerlerine sahip olduğu görüldü. Tüm bileşikler referans bileşiklerden daha düşük inhibisyon potansiyeli gösterdi. PC3 (metoksi türevi) bileşiği hem hCA I hemde hCA II’ye karşı en etkili bileşik olurken, PC5 (flor türevi) AChE'ye karşı seri içinde en güçlü inhibitör etki göstermiştir. Sonuçlar, şalkon türevleri PC3 ve PC5'in hCA I, hCA II ve AChE izoenzimlerine karşı daha güçlü enzim inhibitörleri tasarlamada uygun adaylar olarak kabul edilebileceğini doğrulamıştır.

Design, Synthesis and Biological Activities of Chalcones with Piperonal Moiety

Heterocyclic compounds are of specific significance between pharmacologically active compounds. In this study, some piperonal-based chalcones (PC1-PC10) were synthesized with Claisen-Schmidt Condensation with the reaction between 3,4-methylenedioxybenzaldehyde and several acetophenones. Inhibition potency of the chalcones were evaluated toward human carbonic anhydrase I and II enzymes (hCA I and hCA II), and acetylcholinesterase (AChE). The chalcone derivatives were found to have IC50 values in the range of 5.11- 109.70 μM for hCA I, 17.05-162.59 μM for hCA II, and 18.52-98.69 μM for AChE. All compounds showed lower inhibition potential than reference compounds. While the PC3 (methoxy derivative) compound was the most effective compound against both hCA I and hCA II, PC5 (fluorine derivative) showed the strongest inhibition effect against AChE in the series. Results confirmed that the chalcone derivatives PC3 and PC5 can be considered as favorable candidates against hCA I, hCA II and AChE isoenzymes to design more potent enzyme inhibitors.

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