Pirolidin halkası bulunduran potansiyel biyoaktif yeni bileşiklerin sentezi ve yapılarının aydınlatılması

Abstract

ÖZETBu çalışmada, pirolidin halkası bulunduran bazı yeni siklik ve bisiklikarilaminokarbotiyol türevleri sentezlenerek yapıları aydınlatıldı.Siklik arilaminokarbotiyol pirolidin türevi olarak; T r i m e t i l 1 -(benzoilaminokarbotiyol)-5-(2-naftil)-pirolidin-2,3,4-trikarboksilat (BK1 ), Dimetil 1-(benzoilaminokarbotiyol)-2-sec-butil-5-fenil-pirolidin-2,4-dikarboksilat (BK2 ), Dimetil(BK3 )1-(benzoilaminokarbotiyol)-5-fenil-2- izobutil-pirolidin-2,4-dikarboksilatbileşikleri sentezlendi. Bisiklik olarak; M e t i l 2 -(benzoilaminokarbotiyol)-3-(2-bromopiridin- 3 - il) -1,5 -dimetil -4,6 -dioksooktahidropirolo [3,4-c] pirol -1-karboksilat(BK4 ) ve Metil 2-(benzoilaminokarbotiyol)-3-(2-iyodofenil)-1,5-dimetil-4,6-dioksooktahidropirolo[3,4-c]pirol-1-karboksilat (BK5 ) bileşikleri elde edildi.Bununla birlikte bu çalışmada aynı yöntemle pirolidin halkası bulunduran, Metil2-(1H-indol-3- il- metil)-5- fenil-4-(fenilsülfonil)pirolidin-2-karboksilat ( İK1 ) ve etil 1-(1H- indol-3-il- metil)-3,5-difenil-4,6-dioksooktahidro pirolo[3,4-c]pirol-1-karboksilat(İK2 ) gibi iki yeni triptofan türevi de elde edildi.Sentezlenen bu bileşiklerin yapıları 1 H-NMR, 13C-NMR, 2 D-COSY, DEPT, FT-IR, MS ve elementel analiz teknikleriyle aydınlatıldı. Bu bileşiklerden Trimetil 1-(benzoilaminokarbotiyol)-5-(2-naftil)-pirolidin-2,3,4-trikarboksilat (BK 1 ) bileşiğininyapısı ve sterokimyası tek kristal X- ışıları kırınımı tekniğiyle aydınlatıldı.Anahtar Kelimeler: Aminokarbotiyol pirolidinler, arilizotiyosiyanat, azometinyilür, 1,3-dipolar halkalı katılma tepkimeleri ve triptofan.xiii

ABSTRACTIn this study, some novel cyclic- and bicyclic-aminocarbothioyl compoundsincluding pyrrolidine ring were prepared and their structure were determined.As the cyclic1-arylaminokarbotiyol pirolidines; t r i m e t h y l 1-(benzoylaminocarbothioyl)-5-(2-napthyl)-pyrrolidine-2,3,4-tricarboxylate ( B K 1 ), dimethyl 1-(benzoylaminocarbothioyl)-2-sec-butyl-5-phenyl pyrrolidine-2,4-dicarboxylate (BK2 ),dimethyl 1 -(benzoylaminocarbothioyl)- isobutyl-5-phenyl-pyrrolidine-2,4-dicarboxylate(BK3 ) were synthesized. As the bicyclic derivatives; methyl 2-(benzoylaminocarbonothioyl)-3-(2-bromopyridin-3-yl)-1,5-dimethyl-4,6-dioxoocta hydropyrrolo[3,4-c]pyrrole-1-carboxylate (BK4 ) and methyl 2-(benzoylamino carbonothioyl)-3-(2-iodophenyl)-1,5-dimethyl-4,6-dioxooctahydropyrrolo [3,4-c] pyrrole-1-carboxylate(BK5 ) were reported.In addition to this, two novel tryptophane derivatives including pyrrolidine ring;m e t h y l 2 -(1H-indol-3-ylmethyl)-5-phenyl-4-(phenylsulfinyl)pyrrolidine-2-carboxylate(İK1 ) and ethyl 1-(1H- indol-3-ylmethyl)-3,5-diphenyl-4,6-dioxoocta hydropyrrolo[3,4-c]pyrrole-1-carboxylate (İK2 ) were prepared in a similar manner.The prepared novel compounds were charecterised by 1 H-NMR, 13C-NMR, 2 D-COSY, DEPT, FT-IR, MS and micro analyses. The structure and stereochemistry oftrimethyl 1-(benzoylaminocarbothioyl)-5-(2-napthyl)-pyrrolidine-2,3,4-tricarboxylate1(BK ) was also confirmed by X-ray single crystal structure analysis.Keywords: Aminocarbothioyl pyrrolidines; arylisothiocyanate, azomethineylide, 1,3-dipolar cycloaddition reactions, and tryptophane.xiv