5-amino-1,3,4-tiyadiazol-2-sülfonamid`in çeşitli pirazol karboksilik asit türevlerinin sentezi

Abstract

5-AM NO-1,3,4-T YAD AZOL-2-SÜLFONAM D' N ÇEŞ TL P RAZOLKARBOKS L K AS T TÜREVLER N N SENTEZSevcan KALENDERKimya Bölümü, Yüksek Lisans Tezi, 2007Tez 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.

THE SYNTHESIS OF VARIOUS PYRAZOLE CARBOXYLIC ACID DERIVATIVESOF 5-AMINO-1,3,4-THIADIAZOLE-2-SÜLFONAM DESevcan KALENDERChemistry Department, M.S. Thesis, 2007Thesis 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.