Publication: Benzotiyazol halkası içeren olası antiviral ve antikanser etkili 4-tiyazolidinon türevleri üzerinde çalışmalar
Abstract
ÖZETAmaç: Literatürde 5-ariliden-2-imino-1,3-tiyazolidin-4-on türevlerinin antiviral, antienflamatuvar ve antikanser etkilerine sıkça rastlanmakta olup, son yıllarda anabilim dalımızda yapılan çalışmalarda antiviral ve antikanser aktivite gösteren yeni 5-ariliden-2-imino-1,3-tiyazolidin-4-on türevlerinin sentezlenmesi bizi bu yönde çalışmaya teşvik etmiştir.Gereç ve Yöntem: Çalışmamızda, 5-ariliden-2-imino-1,3-tiyazolidin-4-on türevlerinin sentezinde başlangıç maddesi olarak 6-(triflorometoksi)-1,3-benzotiyazol-2-amin (riluzol) kullanılmıştır. Bu bileşiğin DCM içerisinde TEA varlığında kloroasetil klorür ile tepkimesinden 2-kloro-N-[6-(triflorometoksi)-1,3-benzotiyazol-2-il]asetamit [1] sentezlenmiştir. Elde edilen bileşik [1]’in etanol içerisinde amonyum tiyosiyanat ile tepkimesiyle 4-tiyazolidinon halkası kapatılarak 2-{[6-(triflorometoksi)-1,3-benzotiyazol-2-il]imino}-1,3-tiyazolidin-4-on [2] bileşiği elde edilmiştir. Son aşamada sodyum metoksit varlığında bileşik [2]’nin çeşitli aromatik aldehitler ile Knoevenagel kondensasyonu sonucunda 5-ariliden-2-imino-1,3-tiyazolidin-4-on [3-12] türevi bileşikler kazanılmıştır.Bulgular: Tez çalışmamızda riluzolden hareketle %44 verimle bileşik 1 elde edilmiştir. Bileşik 1’in etanol içerisinde amonyum tiyosiyanatla tepkimesinden %27 verimle 2-imino-tiyazolidin-4-on halkası [2] kapatılmıştır. Halkanın çeşitli aldehitlerle sodyum metoksit içerisinde Knoevenagel kondensasyonu sonucunda bileşik 3-12 %6-62 verimle başarıyla elde edilmiştir.Sonuç: Sentezlenen bileşiklerin saflık kontrolleri İTK yöntemi ile yapılmıştır. Bileşiklerin yapısı erime derecesi tayini ve elementel analiz bulgularının yanısıra, 1H-NMR, FTIR, Kütle ve HMBC spektral verileri kullanılarak kanıtlanmıştır.
SUMMARYAim: Anti-viral, anti-inflammatory and anti-cancer effects of 5-arylidene-2-imino-1,3-thiazolidine-4-one derivatives have been frequently reported in the literature. Synthesis of 5-arylidene-2-imino-1,3-thiazolidine-4-one derivatives with anti-viral and anti-cancer activity at our department in recent years has encouraged us to work in this field.Material and Method: 6-(Trifluoromethoxy)-1,3-benzothiazol-2-amine (riluzole) was used as the starting compound in the synthesis of 5-arylidene-2-imino-1,3-thiazolidine-4-one derivatives, which comprise the subject of our thesis. By reacting this compound with chloroacetyl chloride in DCM and in the presence of TEA, 2-chloro-N-[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]acetamide [1] was synthesized. By reacting [1] with ammonium thiocyanate in ethanol, 4-thiazolidinone ring was closed and thus 2-{[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]imino}-1,3-thiazolidine-4-one [2] was obtained. In the last step, compounds 3-12 were obtained as a result of Knoevenagel condensation of [2] in sodium methoxide with various aromatic aldehydes.Findings: In our thesis study, compound 1 was synthesized starting with riluzole by 44% yield. By reacting [1] with ammonium thiocyanate in ethanol, 2-imino-thiazolidine-4-one ring was closed with 27% yield. Knoevenagel condensation of the ring in sodium methoxide with various aromatic aldehydes successfully gave 5-arylidene-2-imino-1,3-thiazolidine-4-one derivatives with 6-62% yield.Result: Purity of the synthesized compounds was evaluated by TLC method. Structures of the compounds were shown by using 1H-NMR, FTIR, Mass and HMBC spectral data, in addition to melting point and elemental analysis.
SUMMARYAim: Anti-viral, anti-inflammatory and anti-cancer effects of 5-arylidene-2-imino-1,3-thiazolidine-4-one derivatives have been frequently reported in the literature. Synthesis of 5-arylidene-2-imino-1,3-thiazolidine-4-one derivatives with anti-viral and anti-cancer activity at our department in recent years has encouraged us to work in this field.Material and Method: 6-(Trifluoromethoxy)-1,3-benzothiazol-2-amine (riluzole) was used as the starting compound in the synthesis of 5-arylidene-2-imino-1,3-thiazolidine-4-one derivatives, which comprise the subject of our thesis. By reacting this compound with chloroacetyl chloride in DCM and in the presence of TEA, 2-chloro-N-[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]acetamide [1] was synthesized. By reacting [1] with ammonium thiocyanate in ethanol, 4-thiazolidinone ring was closed and thus 2-{[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]imino}-1,3-thiazolidine-4-one [2] was obtained. In the last step, compounds 3-12 were obtained as a result of Knoevenagel condensation of [2] in sodium methoxide with various aromatic aldehydes.Findings: In our thesis study, compound 1 was synthesized starting with riluzole by 44% yield. By reacting [1] with ammonium thiocyanate in ethanol, 2-imino-thiazolidine-4-one ring was closed with 27% yield. Knoevenagel condensation of the ring in sodium methoxide with various aromatic aldehydes successfully gave 5-arylidene-2-imino-1,3-thiazolidine-4-one derivatives with 6-62% yield.Result: Purity of the synthesized compounds was evaluated by TLC method. Structures of the compounds were shown by using 1H-NMR, FTIR, Mass and HMBC spectral data, in addition to melting point and elemental analysis.