The synthesıs of thıourea derıvatıve of benzımıdazole compounds and the ınvestıgatıon of theır catalytıc and bıologıcal actıvıtıes
Küçük Resim Yok
Tarih
2013
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Ege Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Bu çalışmada L-metiyonin, L-izolösin, D-fenilglisin ve L-fenilalanin başlangıç amino asitleri olarak kullanıldı. Deneysel çalışmalar, bu basit amino asitlerin benzimidazol türevi tiyoüre bileşiklerin sentezleri üzerinde oluşturuldu. L-metiyonin?in koruyucu ditersiyer bütil dikarbonat tepkimesi sonucu sırasıyla N-Boc-L-metiyonin hazırlandı. N-Boc-L-metiyonin ile o-fenilendiamin DCC (N,N-disikloheksilkarbodiimit) varlığında tepkimeye sokulmasıyla N-Boc-kiral amit türevi elde edildi. N-Boc-kiral amit türevi asidik ortamda halkalaşma reaksiyonuna sokularak N-Boc-kiral benzimidazol türevi sentezlenmiş oldu. Elde edilen N-Boc-kiral benzimidazol türevi amin gurubuna bağlı olan koruyucu grup ditersiyer bütil dikarbonat'ı düşürülerek kiral benzimidazol türevi elde edildi. Son aşama olarak da kiral benzimidazol türevi ile 3,5-bis (triflorometil) fenil izotiyosiyanat tepkimeye sokularak istenen tiyoüre bileşiği hazırlandı. Benzer bir şekilde, aynı sentez zincirinin kullanılmasıyla L-izolösin, D-fenilglisin ve L-fenilalanin'nin amino asitler türevi tiyoüre bileşikleri de elde edildi. Ürünlerin yapıları spektroskopik analizler (IR, 1H-NMR, 13C-NMR) ve elementel analiz sonuçları ile karakterize edildi
In this study, L-methionine, L-isoleucine, D-phenylglycine and L-phenylalanine were used as starting amino acids. The experimental works were constituted on the synthesis of thiourea derivative of benzimidazole compounds of these simple amino acids. N-Boc-L-methionine was prepared from the reaction of L-methionine and the protective di-tert-butyl dicarbonate. N-Boc-chiral amide derivative was obtained by the reaction of N-Boc-L-methionine with o-phenylenediamine in the presence of DCC (N,N'-Dicyclohexylcarbodiimide). N-Boc-chiral derivative of benzimidazole was synthesized by inserting N-Boc-chiral amide derivative into cyclization reaction in an acidic environment. The synthesized N-Boc-chiral derivative of benzimidazole was deprotected by reducing the protective group which was connected to amine group for obtaining chiral derivative of deprotected benzimidazole. Finally, the desired thiourea derivative was obtained by the reaction of the deprotected benzimidazole derivative with 3,5-bis(trifluromethyl)phenylisothiocyanate. Similarly, thiourea derivatives of the rest amino acids such as L-isoleucine, D-phenylglycine and L-phenylalanine were also obtained by using the same synthetic pathway. The products were characterized by spectroscopic methods (IR, 1H-NMR, 13C-NMR) and elemental analysis.
In this study, L-methionine, L-isoleucine, D-phenylglycine and L-phenylalanine were used as starting amino acids. The experimental works were constituted on the synthesis of thiourea derivative of benzimidazole compounds of these simple amino acids. N-Boc-L-methionine was prepared from the reaction of L-methionine and the protective di-tert-butyl dicarbonate. N-Boc-chiral amide derivative was obtained by the reaction of N-Boc-L-methionine with o-phenylenediamine in the presence of DCC (N,N'-Dicyclohexylcarbodiimide). N-Boc-chiral derivative of benzimidazole was synthesized by inserting N-Boc-chiral amide derivative into cyclization reaction in an acidic environment. The synthesized N-Boc-chiral derivative of benzimidazole was deprotected by reducing the protective group which was connected to amine group for obtaining chiral derivative of deprotected benzimidazole. Finally, the desired thiourea derivative was obtained by the reaction of the deprotected benzimidazole derivative with 3,5-bis(trifluromethyl)phenylisothiocyanate. Similarly, thiourea derivatives of the rest amino acids such as L-isoleucine, D-phenylglycine and L-phenylalanine were also obtained by using the same synthetic pathway. The products were characterized by spectroscopic methods (IR, 1H-NMR, 13C-NMR) and elemental analysis.
Açıklama
Anahtar Kelimeler
Kimya, Chemistry
