Benzotiyazol içeren Schiff bazı türevlerinin sentezi, karakterizasyonu, antioksidan ve enzim aktivitelerinin incelenmesi
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Dosyalar
Tarih
2023
Yazarlar
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Yayıncı
Bursa Teknik Üniversitesi, Lisansüstü Eğitim Enstitüsü
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Benzotiyazol, yapısında azot ve kükürt atomu bulunduran heterosiklik bir bileşiktir. Yapısında azot, kükürt, oksijen gibi heteroatom içeren yapıların farmakolojik aktivite gösterdiği bilinmektedir. Benzotiyazol bileşiğinin 2-konumundan türevlendirilmeleri ile biyolojik aktivitenin önemli ölçüde değiştiği yapılan yapı-aktivite çalışmaları sonucu ortaya konulmuştur. Bu sebeple benzotiyazol bileşiklerinin 2-konumundan türevlendirilmeleri ve biyolojik aktivitelerinin incelenmesi literatürde önemli bir yere sahiptir. Benzotiyazollerin 2-konumundan türevlendirilmelerinde amin türevi benzotiyazol bileşikleri kullanılarak, farklı aldehit ve ketonlarla reaksiyonları sonucunda Schiff bazı bileşikleri elde edilebilmektedir. Schiff bazları azometin fonksiyonel grubunu (-C=N) içerirler ve literatürde biyolojik aktiviteleri çokça çalışılan bileşikler arasında yer almaktadırlar. Azometin grubunun azot atomu üzerindeki ortaklanmamış elektronların, hücre bileşenlerinin aktif merkezleri arasında hidrojen bağı oluşturarak hücre süreçlerini etkilediği bilinmektedir. Bu sebeple benzotiyazol iskeleti içeren Schiff bazlarının biyolojik olarak etkin olacağı görülmektedir. Literatürde biyolojik olarak etkin olan bu iki birimin birleştirilmesiyle sentezlenen türevlerin antikanser, antimikrobiyal, antimalarial ve fungisidal gibi çok çeşitli biyolojik aktiviteler sergilediği bildirilmiştir. Bu tez çalışması kapsamında, 7 tanesi orijinal olan 12 hedef benzotiyazol-azometin bileşiği (3a-3l) sentezlenmiştir. Sentezlenen tüm yapıların spektroskopik karakterizasyonları FT-IR, UV-gör, 1H NMR ve 13C NMR spektroskopik yöntemleri ile yapılmıştır. Sentezlenen türevlerde enol-imin ve keto-amin tautomer dengesi gözlenmiş ve DMF organik çözücüsü içinde asidik ve bazik ortamlarda UV-gör spektroskopik yöntemi ile ölçümü yapılarak bu tautomer dengesi incelenmiştir. Bileşiklerin bazik ortamda keto-amin formunu , asidik ortamda ise enol-imin formunu tercih ettikleri belirlenmiştir. Sentezlenen tüm türevlerin antioksidan ve enzim aktiviteleri incelenmiştir. Antioksidan aktivite ölçümleri 2,2-difenil-1-pikrilhidrazil radikal süpürücü kapasite (DPPH) yöntemi ve demir(III) iyonu indirgeyici antioksidan gücü (FRAP) yöntemi olmak üzere iki farklı yöntem kullanılarak yapılmıştır. Her iki yöntemin de antioksidan aktivite sonuçları incelendiğinde en yüksek aktiviteyi (3j-3l) bileşiklerinin gösterdiği belirlenmiştir. Bileşiklerin enzim aktiviteleri de 4 farklı enzim türüne karşı çalışılmıştır. Bu enzimler α-glukozidaz, tirosinaz, asetilkolinesteraz ve bütirilkolinesteraz enzimleridir. Sentezlenen benzotiyazol-azometin türevlerinden sadece (3g-3ı) türevlerinin α-glukozidaz enzimine karşı iyi enzim inhibisyon aktivitesi gösterdiği belirlenmiştir. Diğer enzim türlerine aktivite göstermemesi, (3g-3ı) türevlerinin belli bir enzime karşı seçici olduğunu göstermektedir.
Benzothiazole is a heterocyclic compound containing nitrogen and sulfur atoms. It is known that structures containing heteroatoms such as nitrogen, sulfur and oxygen show pharmacological activity. Structure-activity studies have revealed that the biological activity of benzothiazole compounds changes significantly with their derivatization from the 2-position. For this reason, 2-position derivatizations of benzothiazole compounds and the investigation of their biological activities have an important place in the literature. In the derivatization of benzothiazoles from the 2- position, Schiff bases can be obtained by reactions of amine derived benzothiazole compounds with different aldehydes and ketones. Schiff bases contain the azomethine functional group (-C=N) and their biological activities are widely studied in the literature. It is known that the unshared electrons on the nitrogen atom of the azomethine group affect cell processes by forming hydrogen bonds between the active centers of cell components. For this reason, it is expected that Schiff bases containing a benzothiazole skeleton will be biologically active. It has been reported in the literature that the derivatives synthesized by combining these two biologically active units exhibit a wide variety of biological activities such as anticancer, antimicrobial, antimalarial and fungicidal. Within the scope of this thesis, 12 target benzothiazole-azomethine compounds (3a3l), 7 of which are original, were synthesized. Spectroscopic characterizations of all synthesized structures were carried out by FT-IR, UV-vis, 1H NMR and 13C NMR methods. The enol-imine and keto-amine tautomer equilibrium was observed in the synthesized derivatives and the tautomer equilibrium was investigated by UV-visible spectroscopic measurement in DMF organic solvent in acidic and basic media. It was determined that the compounds prefer keto-amine form in basic medium and enolimine form in acidic medium. Antioxidant and enzyme activities of all synthesized derivatives were investigated. Antioxidant activity measurements were carried out using two different methods: 2,2-diphenyl-1-picrylhydrazyl radical scavenging capacity (DPPH) and ferric reducing antioxidant power (FRAP) methods. When the antioxidant activity results of both methods were analyzed, it was determined that (3j-3l) compounds showed the highest activity. The enzyme activities of the compounds were also studied against 4 different enzyme types. These enzymes are α-glucosidase, tyrosinase, acetylcholinesterase and butyrylcholinesterase. Among the synthesized benzothiazole-azomethine derivatives, only (3g-3i) derivatives showed good enzyme inhibition activity against α-glucosidase enzyme. The lack of activity against other types of enzymes indicates that the (3g-3i) derivatives are selective for a certain enzyme.
Benzothiazole is a heterocyclic compound containing nitrogen and sulfur atoms. It is known that structures containing heteroatoms such as nitrogen, sulfur and oxygen show pharmacological activity. Structure-activity studies have revealed that the biological activity of benzothiazole compounds changes significantly with their derivatization from the 2-position. For this reason, 2-position derivatizations of benzothiazole compounds and the investigation of their biological activities have an important place in the literature. In the derivatization of benzothiazoles from the 2- position, Schiff bases can be obtained by reactions of amine derived benzothiazole compounds with different aldehydes and ketones. Schiff bases contain the azomethine functional group (-C=N) and their biological activities are widely studied in the literature. It is known that the unshared electrons on the nitrogen atom of the azomethine group affect cell processes by forming hydrogen bonds between the active centers of cell components. For this reason, it is expected that Schiff bases containing a benzothiazole skeleton will be biologically active. It has been reported in the literature that the derivatives synthesized by combining these two biologically active units exhibit a wide variety of biological activities such as anticancer, antimicrobial, antimalarial and fungicidal. Within the scope of this thesis, 12 target benzothiazole-azomethine compounds (3a3l), 7 of which are original, were synthesized. Spectroscopic characterizations of all synthesized structures were carried out by FT-IR, UV-vis, 1H NMR and 13C NMR methods. The enol-imine and keto-amine tautomer equilibrium was observed in the synthesized derivatives and the tautomer equilibrium was investigated by UV-visible spectroscopic measurement in DMF organic solvent in acidic and basic media. It was determined that the compounds prefer keto-amine form in basic medium and enolimine form in acidic medium. Antioxidant and enzyme activities of all synthesized derivatives were investigated. Antioxidant activity measurements were carried out using two different methods: 2,2-diphenyl-1-picrylhydrazyl radical scavenging capacity (DPPH) and ferric reducing antioxidant power (FRAP) methods. When the antioxidant activity results of both methods were analyzed, it was determined that (3j-3l) compounds showed the highest activity. The enzyme activities of the compounds were also studied against 4 different enzyme types. These enzymes are α-glucosidase, tyrosinase, acetylcholinesterase and butyrylcholinesterase. Among the synthesized benzothiazole-azomethine derivatives, only (3g-3i) derivatives showed good enzyme inhibition activity against α-glucosidase enzyme. The lack of activity against other types of enzymes indicates that the (3g-3i) derivatives are selective for a certain enzyme.
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Anahtar Kelimeler
Kimya, NATURAL SCIENCES::Chemistry
