5-amino-1,3,4-tiyadiazol-2-sülfonamid'in çeşitli pirazol karboksilik asit türevlerinin sentezi
The synthesis of various pyrazole carboxylic acid derivatives of 5-amino-1,3,4-thiadiazole-2-sülfonamide
Yazar: SEVCAN KALENDER
Danışman: YRD. DOÇ. DR. RAHMİ KASIMOĞULLARI
Dumlupınar Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı
Derece: Yüksek Lisans, 2007
Konu: Kimya = Chemistry

Özet:
Tez Danışmanı: Yrd. Doç. Dr. Rahmi KASIMOĞULLARIÖZETPirazol karboksilik asit türevleri antipretik, analjezik ve anti-inflammatuar özelliklerisebebiyle önemli heterosiklik bileşiklerdir. 5-amino-1,3,4-tiyadiazol-2-sülfonamid, glaucomahastalığı tedavisi için kullanılan önemli bir bileşiktir.Yaptığımız bu çalışmada, öncelikle pirazol karboksilik asit türevleri, SOCl2 ile asitklorürlere dönüştürülerek aktifleştirildi. Bu klorürlerin, 5-amino-1,3,4-tiyadiazol-2-sülfonamidbileşiği ile reaksiyonları sonucu amid bileşikleri sentezlendi.Sentezlenen bütün bileşiklerin yapıları IR,1H-NMR ve 13C-NMR spektroskopisi ileaydınlatıldı. simleri aşağıda verilmiştir;4-benzoil-1-(3-nitrofenil)-5-fenil-N-(5-Sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid, 4-benzoil-1-(4-nitrofenil)-5-fenil-N-(5-sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid, 4-benzoil-1,5-difenil-N-(5-sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid, etil-1,5-difenil-3-(5-sülfamoil-1,3,4-tiyadiazol-2-ilkarbamoil)-1H-pirazol-4-karboksilat, etil 1-(3-nitrofenil)-5-fenil-3-(5-sülfamoil-1,3,4-tiyadiazol-2-ilkarbamoil)-1H-pirazol-4-karboksilat, etil 1-(4-nitrofenil)-5-fenil-3-(5-sülfamoil-1,3,4-tiyadiazol-2-ilkarbamoil)-1H-pirazol-4-karboksilat, 1-(3-aminofenil)-4-benzoil-5-fenil-N-(5-sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid, 1-(4-aminofenil)-4-benzoil-5-fenil-N-(5-sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid, etil 1-(3-aminofenil)-5-fenil-3-(5-sülfamoil-1,3,4-tiyadiazol-2-ilkarbamoil)-1H-pirazol-4-karboksilat.Anahtar kelimeler: Pirazol karboksilik asitler, 1,3,4-tiyadiazol-2-sülfonamid, glaucoma.

Abstract:
Thesis Supervisor: Yrd. Doç.Dr. Rahmi KASIMOĞULLARISUMMARYPyrazole carboxylic acid derivatives are attractive heterocyclic composites because oftheir antipretic, analgesic and anti-inflammatuar characteristics. 5-amino-1,3,4-thiadiazole-2-sülfonamide is an important compound that used for the treatment of glaucoma.In our study, first of all, pyrazole carboxylic acid derivatives have been transformed toacid chlorides with SOCl2. Then amide compounds have been synthesized from the reactionbetween chloride derivatives of pyrazole carboxylic acids and 5-amino-1,3,4-thiadiazole-2-sülfonamide.The structures of all obtained compounds have been characterized by means of IR,1H-NMR,13C-NMR spectroscopies and named as the followings;4-benzoyl-1-(3-nitrophenyl)-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, 4-benzoyl-1,5-diphenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, ethyl 1,5-diphenyl-3-(5-sulfamoyl-1,3,4-thiadiazol-2-ylcarbamoyl)-1H-pyrazole-4-carboxylate, ethyl 1-(3-nitrophenyl)-5-phenyl-3-(5-sulfamoyl-1,3,4-thiadiazol-2-ylcarbamoyl)-1H-pyrazole-4-carboxylate, ethyl 1-(4-nitrophenyl)-5-phenyl-3-(5-sulfamoyl-1,3,4-thiadiazol-2-ylcarbamoyl)-1H-pyrazole-4-carboxylate, 1-(3-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, 1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, ethyl 1-(3-aminophenyl)-5-phenyl-3-(5-sulfamoyl-1,3,4-thiadiazol-2-ylcarbamoyl)-1H-pyrazole-4-carboxylate.Key words : Pyrazole carboxylic acids, 1,3,4-thiadiazole-2-sülfonamide, glaucoma.