Biyolojik etkili yeni bazı tiyazolidindion türevleri üzerinde sentez çalışmaları
Studies on the synthesis of some new thiazolidinedione derivatives possesing biological activity
- Tez No: 203027
- Danışmanlar: DOÇ.DR. OYA BOZDAĞ DÜNDAR
- Tez Türü: Yüksek Lisans
- Konular: Eczacılık ve Farmakoloji, Pharmacy and Pharmacology
- Anahtar Kelimeler: Antidiyabetik aktivite, 4-tiyazolidindion, tiyazol, tiyazoliltiyazolidindion
- Yıl: 2007
- Dil: Türkçe
- Üniversite: Ankara Üniversitesi
- Enstitü: Sağlık Bilimleri Enstitüsü
- Ana Bilim Dalı: Farmasötik Kimya Ana Bilim Dalı
- Bilim Dalı: Belirtilmemiş.
- Sayfa Sayısı: 156
Özet
Antidiyabetik Etkili Bazı Bilesikler Üzerinde Arastırmalar Bu çalısmada, 2,4-tiyazolidindion bilesiginin 3. ve 5. konumundan sübstitüe yeni bazı 2,4- tiyazolidindion türevlerinin sentezleri ve bunların antidiyabetik aktivitelerinin incelenmesi amaçlandı. Bilesiklerin Sentezi: 5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-3-( p- ve/veya o- sübstitüe benzil)-1,3- tiyazolidin-2,4-dion sentezi: 1) 2,4-TZD sentezi 2) 3-(p- ve/veya o- sübstitüe benzil)-1,3-tiyazolidin-2,4-dion sentezi 3) 4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-karbaldehid sentezi gerçeklestirildi. 4) Daha sonra 3-( p- ve/veya o- sübstitüe benzil)-1,3-tiyazolidin-2,4-dion ve 4-kloro-2-[(2- feniletil)tiyo]-1,3-tiyazol-5-karbaldehid bilesiklerinden hareketle 2,4-tiyazolidindion türevi 6 orijinal bilesik sentez edildi. Ia:3-benzil-5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-1,3-tiyazolidin-2,4-dion Ib:3-(4-florobenzil)-5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-1,3-tiyazolidin- 2,4-dion Ic:3-(4-klorobenzil)- 5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-1,3-tiyazolidin- 2,4-dion Id:3-(4-bromobenzil)- 5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-1,3-tiyazolidin- 2,4-dion Ie:5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-3-(2,4-diklorobenzil)-1,3- tiyazolidin-2,4-dion If:3-(4-nitrobenzil)-5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-1,3-tiyazolidin- 2,4-dion 5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-3-[2-( p- ve/veya o- sübstitüe fenil)-2- oksoetil]-1,3-tiyazolidin-2,4-dion sentezi: 1) 2,4-TZD sentezi 2) 3-[2-( p- ve/veya o- sübstitüe fenil)-2-oksoetil]-1,3-tiyazolidin-2,4-dion sentezi 3) 4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-karbaldehid sentezi gerçeklestirildi. 4) Daha sonra 3-[2-( p- ve/veya o- sübstitüe fenil)-2-oksoetil]-1,3-tiyazolidin-2,4-dion ve 4- kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-karbaldehit bilesiklerinden hareketle 2,4-tiyazolidindion türevi 6 orijinal bilesik sentez edildi. IIa:5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-3-[2-fenil-2-oksoetil]-1,3- tiyazolidin-2,4-dion IIb:5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-3-[2-(4-florofenil)-2-oksoetil]- 1,3-tiyazolidin-2,4-dion IIc:5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-3-[2-(4-klorofenil)-2-oksoetil]- 1,3-tiyazolidin-2,4-dion IId:5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-3-[2-(4-bromofenil)-2-oksoetil]- 1,3-tiyazolidin-2,4-dion IIe:5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-3-[2-(2,4-diklorofenil)-2- oksoetil]-1,3-tiyazolidin-2,4-dion IIf: 5-({4-kloro-2-[(2-feniletil)tiyo]-1,3-tiyazol-5-il}metilen)-3-[2-(4-nitrofenil)-2-oksoetil]- 1,3-tiyazolidin-2,4-dion 3-[2-(p- ve/veya o-sübstitüe fenil)-2-okso-etil]-5-(2,4-dikloro-tiyazol-5-il-metilenil)- tiyazolidin-2,4-dion sentezi için: 1) 2,4-TZD sentezi, 2) 2,4-dikloro-1,3-tiyazol-5-karbaldehid sentezi, 3) 3-[2-( p- ve/veya o- sübstitüe fenil)-2-oksoetil]-1,3-tiyazolidin-2,4-dion sentezi gerçeklestirildi. 4) Daha sonra 2,4-dikloro-1,3-tiyazol-5-karbaldehit ve 3-[2-( p- ve/veya o- sübstitüe fenil)-2- oksoetil]-1,3-tiyazolidin-2,4-dion bilesiklerinden hareketle 2,4-tiyazolidindion türevi 6 orijinal bilesik sentez edildi. IIIa:3-(2-fenil-2-okso-etil)-5-(2,4-dikloro-tiyazol-5-il-metilenil)-tiyazolidin-2,4-dion IIIb:3-[2-(4-floro-fenil)-2-okso-etil]-5-(2,4-dikloro-tiyazol-5-il-metilenil)-tiyazolidin-2,4-dion IIIc:3-[2-(4-kloro-fenil)-2-okso-etil]-5-(2,4-dikloro-tiyazol-5-il-metilenil)- tiyazolidin-2,4-dion IIId:3-[2-(4-bromo-fenil)-2-okso-etil]-5-(2,4-dikloro-tiyazol-5-il-metilenil)-tiyazolidin-2,4- dion IIIe:3-[2-(2,4-dikloro-fenil)-2-okso-etil]-5-(2,4-dikloro-tiyazol-5-il-metilenil)- tiyazolidin-2,4- dion IIIf:3-[2-(4-nitro-fenil)-2-okso-etil]-5-(2,4-dikloro-tiyazol-5-il-metilenil)-tiyazolidin-2,4-dion Elde edilen bilesiklerin saflıkları TK ile kontrol edildikten sonra ergime noktaları saptandı ve yapıları IR, 1H NMR, Mass ve Elementel analiz verileri ile kanıtlandı. 3-[2-(4-Kloro fenil)-2-okso-etil]-5-(2,4-dikloro-tiyazol-5-il-metilenil)- tiyazolidin-2,4-dion (IIIc) bilesiginin konformasyonel yapısı X-Ray kristallografik analizi ile aydınlatılmıstır. Buna göre IIIc bilesiginin Z izomer yapısında oldugu görülmüstür.
Özet (Çeviri)
Studies on Some Chemical Compounds With Antidiabetic Activity In this study, it was aimed to investigate the synthesis and the antidiabetic activity of some new 2,4-thiazolidinedione derivatives which are substituted at 3. and 5. positions of 2,4-TZD ring. Synthesis of the compounds: Synthesis of 5-({4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-yl}methylene)-3-(p- and/or osubstitue benzyl)-1,3-thiazolidine-2,4-dione: 1) Synthesis of 2,4-TZD 2) 3-(p- and/or o- substitute benzyl)-1,3- thiazolidine-2,4-dione 3) 4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-carbaldehyde was synthesized. 4) 6 original 2,4-thiazolidinedione derivatives were synthesized with reaction of 3-(p- and/or osubstitute benzyl)-1,3- thiazolidine-2,4-dione and 4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole- 5-carbaldehyde. Ia:3-benzyl-5-({4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-yl}methylene)-1,3- thiazolidine-2,4-dione Ib:3-(4-fluorobenzyl)-5-({4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-yl} methylene)-1,3- tiyazolidine-2,4-dione Ic:3-(4-chlorobenzyl)-5-({4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-yl} methylene)-1,3- tiyazolidine-2,4-dione Id:3-(4-bromobenzyl)-5-({4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-yl} methylene)-1,3- tiyazolidine-2,4-dione Ie:5-({4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-yl}methylene)-3-(2,4-dichlorobenzyl)- 1,3-tiyazolidine-2,4-dione If:3-(4-nitrobenzyl)-5-({4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-yl} methylene)-1,3- thiazolidine-2,4-dione Synthesis of 5-({4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-yl}methylene)-3-[2-( pand/ or o- substitute phenyl)-2-oxoethyl]-1,3- thiazolidine-2,4-dione 1) Synthesis of 2,4-TZD 2) 3-[2-( p- and/or o- substitute phenyl)-2-oxoethyl]-1,3- thiazolidine-2,4-dione 3) 4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-carbaldehyde was synthesized. 4) 6 original 2,4-thiazolidinedione derivatives were synthesized with reaction of 3-[2-( pand/ or o- substitute phenyl)-2-oxoethyl]-1,3- thiazolidine-2,4-dione and 4-chloro-2-[(2- phenylethyl)thio]-1,3-thiazole-5-carbaldehyde. IIa:5-({4-chloro-2-[(2- phenylethyl)thio]-1,3-thiazole-5-yl}methylene)-3-[2-phenyl-2- oxoethyl]-1,3- thiazolidine-2,4-dione IIb: 5-({4-chloro-2-[(2- phenylethyl)thio]-1,3-thiazole-5-yl}methylene)-3-[2-(4-fluorophenyl)- 2- oxoethyl]-1,3- thiazolidine-2,4-dione IIc: 5-({4-chloro-2-[(2- phenylethyl)thio]-1,3-thiazole-5-yl}methylene)-3-[2-(4-chlorophenyl)- 2- oxoethyl]-1,3- thiazolidine-2,4-dione IId: 5-({4-chloro-2-[(2- phenylethyl)thio]-1,3-thiazole-5-yl}methylene)-3-[2-(4-bromophenyl)- 2- oxoethyl]-1,3- thiazolidine-2,4-dione IIe: 5-({4-chloro-2-[(2- phenylethyl)thio]-1,3-thiazole-5-yl}methylene)-3-[2-(2,4- dichlorophenyl)-2- oxoethyl]-1,3- thiazolidine-2,4-dione IIf: 5-({4-chloro-2-[(2-phenylethyl)thio]-1,3-thiazole-5-yl}methylene)-3-[2-(4-nitrophenyl)-2- oxoethyl]-1,3- thiazolidine-2,4-dione Synthesis of 3-[2-(p- and/or o-substitute phenyl)-2-oxo-ethyl]-5-(2,4-dichloro-thiazole-5-ylmethylenyl)- thiazolidine-2,4-dione 1) Synthesis of 2,4-TZD 2) Synthesis of 2,4-dichloro-1,3-thiazole-5-carbaldehyde 3) 3-[2-( p- and/or o- substitute phenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione was synthesized. IIIa:3-(2-phenyl-2-oxo-ethyl)-5-(2,4-dichloro-thiazole-5-yl-methylenyl)-thiazolidine-2,4-dione IIIb:3-[2-(4-fluoro-phenyl)-2-oxo-ethyl)-5-(2,4-dichloro-thiazole-5-yl-methylenyl)- thiazolidine-2,4-dione IIIc:3-[2-(4-chloro-phenyl)-2-oxo-ethyl)-5-(2,4-dichloro-thiazole-5-yl-methylenyl)- thiazolidine-2,4-dione IIId:3-[2-(4-bromo-phenyl)-2-oxo-ethyl)-5-(2,4-dichloro-thiazole-5-yl-methylenyl)- thiazolidine-2,4-dione IIIe:3-[2-(2,4-dichloro-phenyl)-2-oxo-ethyl)-5-(2,4-dichloro-thiazole-5-yl-methylenyl)- thiazolidine-2,4-dione IIIf:3-[2-(4-nitro-phenyl)-2-oxo-ethyl)-5-(2,4-dichloro-thiazole-5-yl-methylenyl)-thiazolidine- 2,4-dione By using these three different general methods, 18 original compounds were synthesized which are substitute at 3. and 5. positions of 2,4-TZD. The purity were controlled by TLC and then melting points were determined. The chemical structure of the synthesizen compounds were elucidated by their IR, 1H NMR, Mass, and Elemantary analysis data. Conformationally structure of compound 3-[2-(4-chloro phenyl)-2-oxo-ethyl]-5-(2,4-dichlorothiazole- 5-yl-methylenyl)- thiazolidine-2,4-dione (IIIc) was performed by X-Ray analysis. According to this, it was seen that the compounds IIIc is structure of Z isomer. Key Words : Antidiabetic activity, 2,4-thiazolidinedione, thiazole, thiazolylthiazolidinedione
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