Synthesis, characterization and carbonic anhydrase studies of some new sulfonamido thiazole compounds
Küçük Resim Yok
Tarih
2023
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Bolu Abant İzzet Baysal Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Tiyazoller halka yapısı gereği geniş bir biyolojik aktiviteye sahip olduklarından heterosiklik bileşikler sınıfında önemli bir yere sahiptir ve tıbbi kimya ve farmasötik araştırmalarda yaygın olarak kullanılırlar. Sülfonamidler de önemli biyolojik aktivitelere sahip sülfa-ilaçları olarak bilirinler ve son yıllarda karbonik anhidraz inhibitör özellikleri yoğun şekilde araştırılmaktadır. Bu çalışmada tiyazol bazlı benzensülfonamid moleküllerini içeren otuz farklı yeni molekülün sentezini gerçekleştirdik. İlk çalışmada 2-((4-sülfamoilfenil)amino)tiyazol-4-karboksilik asit ve karşılık gelen alkolleri (çözücü olarak) reflüx koşullarında reaksiyona sokulması ile istenilen moleküller elde edildi. İkinci çalışmada, 4-((4-hidrazinkarbonil)tiyazol-2-il)amino)benzensülfonamid ve siklik aldehitlerin etanol ve reflüx koşullarında reaksiyona girmesiyle yeni molekülleri sentezledik. Spektroskopik yöntemlerle (IR, 1H, 13C NMR, MALDI-TOF MS ve HRMS) yeni bileşiklerin yapıları doğrulandı. Biyolojik olarak aktif yeni bileşikler keşfetme arayışında, 1,3-tiyazol sülfonamid molekülleri, potansiyel karbonik anhidraz inhibitörleri özellikleri sergileyecek şekilde tasarlandı ve sentezlendi. Tüm bileşikler, standart karbonik anhidraz inhibitörüne (AAZ) karşı hCAI, hCAII, hCAIX ve hCAXII izoformlarını inhibe etme yetenekleri açısından test edildi.
Thiazoles have an important place in the class of heterocyclic compounds since they have a wide biological activity due to their ring structure and are widely used in medicinal chemistry and pharmaceutical research. Sulfonamides are also known as sulfa-drugs with important biological activities and their carbonic anhydrase inhibitory properties have been extensively studied in recent years. In this work, we have accomplished a synthesis of thirty different novel molecules containing thiazole based benzenesulfonamide molecules. In the first study, we obtained the desired molecules by the reaction of 2-((4-sulfamoylphenyl)amino)thiazole-4-carboxylic acid and corresponding alcohols (as a solvent) at reflux conditions. In the second study, we sythesized the novel molecules by the reaction of 4-((4-hydrazinecarbonyl)thiazol-2-yl)amino)benzenesulfonamide and cyclic aldehydes in ethanol and reflux condition. The structures of the newly synthesized compounds were confirmed using spectroscopic methods, including IR, 1H NMR, 13C NMR, MALDI TOF-MS and HRMS. In search of discovering novel biologically active compounds, we designed and synthesized 1,3-thiazole sulfonamide molecules, which exhibit potential as carbonic anhydrase inhibitors. All compounds underwent testing to evaluate their ability to inhibit hCAI, hCAII, hCAIX, and hCAXII isoforms in comparison to the standard carbonic anhydrase inhibitor (AAZ).
Thiazoles have an important place in the class of heterocyclic compounds since they have a wide biological activity due to their ring structure and are widely used in medicinal chemistry and pharmaceutical research. Sulfonamides are also known as sulfa-drugs with important biological activities and their carbonic anhydrase inhibitory properties have been extensively studied in recent years. In this work, we have accomplished a synthesis of thirty different novel molecules containing thiazole based benzenesulfonamide molecules. In the first study, we obtained the desired molecules by the reaction of 2-((4-sulfamoylphenyl)amino)thiazole-4-carboxylic acid and corresponding alcohols (as a solvent) at reflux conditions. In the second study, we sythesized the novel molecules by the reaction of 4-((4-hydrazinecarbonyl)thiazol-2-yl)amino)benzenesulfonamide and cyclic aldehydes in ethanol and reflux condition. The structures of the newly synthesized compounds were confirmed using spectroscopic methods, including IR, 1H NMR, 13C NMR, MALDI TOF-MS and HRMS. In search of discovering novel biologically active compounds, we designed and synthesized 1,3-thiazole sulfonamide molecules, which exhibit potential as carbonic anhydrase inhibitors. All compounds underwent testing to evaluate their ability to inhibit hCAI, hCAII, hCAIX, and hCAXII isoforms in comparison to the standard carbonic anhydrase inhibitor (AAZ).
Açıklama
Lisansüstü Eğitim Enstitüsü, Kimya Ana Bilim Dalı
Anahtar Kelimeler
Kimya, Chemistry
