Kaliksarenlerin bazı azol türevlerinin sentezi, karakterizasyonu ve biyolojik özelliklerinin incelenmesi
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2020
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Selçuk Üniversitesi Fen Bilimleri Enstitüsü
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info:eu-repo/semantics/openAccess
Abstract
Bu çalışma imidazol gruplu bazı kaliks[4]aren bileşiklerinin sentezini ve bu bileşiklerin ct-DNA üzerindeki etkilerinin incelenmesini içermektedir. Sentezlenen bileşiklerin yapıları spektroskopik teknikler (FTIR, 1H NMR, kütle) ve element analizi ile aydınlatıldı. p-ter-Bütilkaliks[4] aren (1) bileşiği literatürde belirtilen metoda göre sentezlendi. Daha sonra 1 nolu bileşik metilbromasetat ile K2CO3/aseton ortamında literatüre göre reaksiyona sokularak 2 bileşiği sentezlendi. 2 nolu bileşik NaOH/etanol ortamında hidroliz edilerek kaliksarenin diasit türevine(3), sonra da SOCl2 ile etkileştirilerek kaliksarenin asitklorür türevine(4) dönüştürülmüştür. Kaliksarenin imidazol gruplu amit bileşiğini oluşturmak üzere 4 nolu bileşik 1-(3-aminopropil)imidazol ile THF ortamında tepkimeye sokularak bileşik 5 elde edilmiştir. Elde edilen 5 nolu bileşiğin upper rim üzerinden farklı türevlerini oluşturmak üzere, ilk olarak HMTA/TFA ile dialdehit türevine(6) ve sonrasında farklı primer aminlerle(furfuril amin, sikloheksil amin) Schiff bazı türevlerine(7,8) dönüştürülmüştür. Kaliksarenin hem upper hem de lower rim üzerinden imidazol gruplu türevlerini sentezlemek üzere 2 nolu kaliksarenin diester türevi, HMTA/TFA ile tepkimeye sokulmuştur. Elde edilen 9 nolu bileşiğin 1-(3-aminopropil)imidazol ile reaksiyonundan bileşik 10 elde edilmiştir. Sentezlenen kaliksaren/imidazol bileşiklerinin(5, 7, 8 ve 10) ct-DNA ya karşı etkileri spektrometrik metod ile incelendi.
This study involves the synthesis of some calix [4] arene compounds with imidazole groups and their effects on ct-DNA. The structures of the synthesized compounds were elucidated by spectroscopic techniques (FTIR, 1H NMR, mass) and elemental analysis. p-ter-Butylcalix [4] arene (1) was synthesized according to the method described in the literature. Compound 1 was then reacted with methyl bromo acetate in K2CO3 / acetone medium according to the literature to synthesize compound 2. Compound 2 was converted to the diacid derivative of calixarene (3) by hydrolysis in NaOH /ethanol medium and then to the acid chloride derivative (4) of calixarene by interaction with SOCl2. The compound 4 was reacted with 1- (3-aminopropyl) imidazole in THF medium to form the imidazole group amide compound of calixarene to give compound 5. In order to form different derivatives of the obtained compound 5 over the upper rim, it was first converted to dialdehyde derivative (6) with HMTA / TFA (6) and then to Schiff base derivatives (7,8) with different primary amines (furfuryl amine, cyclohexyl amine). The diester derivative of calixarene 2 was reacted with HMTA/TFA to synthesize imidazole group derivatives of calixarene both on upper and lower rim. The reaction of the obtained compound 9 with 1- (3-aminopropyl) imidazole gave compound 10. The effects of synthesized calixarene / imidazole compounds (5, 7,8 and 10) against ct-DNA were examined via spectrometric method.
This study involves the synthesis of some calix [4] arene compounds with imidazole groups and their effects on ct-DNA. The structures of the synthesized compounds were elucidated by spectroscopic techniques (FTIR, 1H NMR, mass) and elemental analysis. p-ter-Butylcalix [4] arene (1) was synthesized according to the method described in the literature. Compound 1 was then reacted with methyl bromo acetate in K2CO3 / acetone medium according to the literature to synthesize compound 2. Compound 2 was converted to the diacid derivative of calixarene (3) by hydrolysis in NaOH /ethanol medium and then to the acid chloride derivative (4) of calixarene by interaction with SOCl2. The compound 4 was reacted with 1- (3-aminopropyl) imidazole in THF medium to form the imidazole group amide compound of calixarene to give compound 5. In order to form different derivatives of the obtained compound 5 over the upper rim, it was first converted to dialdehyde derivative (6) with HMTA / TFA (6) and then to Schiff base derivatives (7,8) with different primary amines (furfuryl amine, cyclohexyl amine). The diester derivative of calixarene 2 was reacted with HMTA/TFA to synthesize imidazole group derivatives of calixarene both on upper and lower rim. The reaction of the obtained compound 9 with 1- (3-aminopropyl) imidazole gave compound 10. The effects of synthesized calixarene / imidazole compounds (5, 7,8 and 10) against ct-DNA were examined via spectrometric method.
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kaliksaren, calixarene, azol, azole
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Kurşun, A. (2020). Kaliksarenlerin Bazı Azol Türevlerinin Sentezi, Karakterizasyonu Ve Biyolojik Özelliklerinin İncelenmesi. (Yüksek Lisans Tezi). Selçuk Üniversitesi, Fen Bilimler Enstitüsü, Konya.
