Benzoksazolon Türevi Şalkon Bileşiklerinin Sentezi ve Biyoaktivitelerinin Araştırılması

Year 2020, , 334 - 347, 20.03.2020

Sinan Bilginer

https://doi.org/10.18185/erzifbed.672163

Cited By: 2

Abstract

Bu
çalışmada, genel kimyasal yapısı 6-(3-Aril-2-propen-1-oil)-2(3H)-benzoksazolon olan ve aril kısmı
benzen, furan veya tiyofen olarak tasarlanan üç adet bileşik başarıyla
sentezlenmiş ve yapıları ¹H NMR, ¹³C NMR ve HRMS
spektrumları ile aydınlatılmıştır. Bileşik 2,
6-[3-(Furan-2-il)-2-propen-1-oil]-2(3H)-benzoksazolon,
sentezi ile ilk kez bu çalışmada rapor edilmiştir. Sentezlenen bileşiklerin
sitotoksik aktiviteleri (bileşik 1 hariç), karbonik anhidraz inhibitör
aktiviteleri (1-3) ve asetilkolin esteraz inhibitör aktiviteleri (1-3) ise ilk
kez bu çalışma ile rapor edilmiştir. Bileşiklerin tümünün AChE enzim inhibitör
aktiviteleri referans bileşikten yüksekken, sitotoksik ve hCA I/II inhibitör
aktiviteleri referans bileşiklerden düşüktür. Yalnızca bileşik 2, referans
bileşik AZA’ya benzer hCA I inhibisyon göstermiştir. Ayrıca, bileşiklerin aril
kısmına fenil halkasının getirilmesinin, tiyofen veya furan halkasına göre,
sitotoksik ve AChE enzim inhibitör aktiviteleri açısından daha faydalı bir
modifikasyon olduğu bu çalışma ile ortaya konulmuştur. Bundan başka,
sentezlenen bileşiklerin yüksek AChE inhibitör aktiviteleri nedeniyle ileriki
çalışmalar için uygun öncü bileşikler oldukları görülmüştür. 

Keywords

Asetilkolin esteraz, benzoksazolon, karbonik anhidraz, şalkon, sitotoksisite

Supporting Institution

Atatürk Üniversitesi

Project Number

2016/118

Thanks

Çalışma sırasında, bileşiklerin sentezlenmesindeki katkılarından dolayı Prof. Dr. Halise İnci GÜL’e, NMR spektrumlarının yorumlanmasındaki katkılarından dolayı Prof. Dr. Cavit KAZAZ’a, sentezlenen bileşiklerin karbonik anhidraz ve asetilkolin esteraz inhibisyon aktivite çalışmalarındaki katkılarından dolayı Prof. Dr. İlhami GÜLÇİN'e, sitotoksik aktivite çalışmalarındaki katkılarından dolayı Prof. Dr. Hiroshi Sakagami’ye ve çalışmayı destekleyen Atatürk Üniversitesi Araştırma Fon Saymanlığı’na (BAP Proje No: 2016/118) teşekkürlerimi sunarım.

Synthesis and Bioactivities of Benzoxazolone Derivative Chalcone Compounds

Abstract

In
this study, three compounds, 6-(3-aryl-2-propen-1-oyl)-2(3H)-benzoxazolones, whose aryl part is designed as benzene, furan
or thiophene were synthesized successfully and their chemical structures were
confirmed by ¹H NMR, ¹³C NMR, and HRMS spectra. Compound
2, 6-[3-(Furan-2-yl)-2-propen-1-oyl]-2(3H)-benzoxazolone,
was reported for the first time with its synthesis in this study. Cytotoxic
activities (except compound 1), carbonic anhydrase inhibitory activities (1-3)
and acetylcholine esterase (AChE) inhibitory activities (1-3) of synthesized
compounds were reported for the first time in this study. The AChE enzyme
inhibitory activities of all compounds were higher than the reference compound,
while the cytotoxicities and hCA I/II inhibitory activities of the compounds
were lower than the reference compounds. Only compound 2 showed similar
inhibitory activity with reference drug AZA against hCA I. Furthermore, in this
study, it was shown that introducing the phenyl ring as the aryl moiety of the
compounds was a more useful modification than the thiophene or furan rings in
terms of the cytotoxic and AChE enzyme inhibitory activities. On the other
hand, all synthesized compounds were found to be as candidate molecules for
further studies due to their high AChE inhibitory activities.

Keywords

Acetylcholinesterase, benzoxazolone, carbonic anhydrase, chalcone, cytotoxicity

Project Number

2016/118

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