Butirik asit türevi 1,3,4-tiyadiazol bileşiklerinin sentezi, karakterizasyonu ve antimikrobiyal aktivitelerinin belirlenmesi

Abstract

Bu tez çalışmasında 4-Fenoksi butirik asit ile N-fenil tiyosemikarbazit türevlerinin fosfor oksiklorür katalizörlüğündeki reaksiyonundan, 5-[3-fenoksi)propil]-N-[3'-klorofenil]-1,3,4-tiyadiazol-2-amin(1), 5-[3-fenoksi)propil]-N--[4'-klorofenil]-1,3,4-tiyadiazol-2-amin(2), 5-[3-fenoksi)propil]-N-[2'-florofenil]-1,3,4-tiyadiazol-2-amin (3), 5-[3- fenoksi)propil]-N-[3'- florofenil]-1,3,4- tiyadiazol-2-amin(4), 5-[3- fenoksi)propil]-N-[4'- florofenil]-1,3,4- tiyadiazol-2-amin (5), 5-[3- fenoksi)propil]-N-[2'-metoksifenil]-1,3,4- tiyadiazol-2-amin(6), 5-[3-fenoksi)propil]-N-[3'- metoksifenil]-1,3,4- tiyadiazol-2-amin(7),5-[3- fenoksi)propil]-N-[4'- metoksifenil]-1,3,4- tiyadiazol-2-amin(8), 5-[3- fenoksi)propil]-N-[4'-nitrofenil]-1,3,4- tiyadiazol-2-amin (9), 5-[3- fenoksi)propil]-N-[2'-metoksikarbonilfenil]-1,3,4- tiyadiazol-2-amin(10), 5-[3- fenoksi)propil]-N-benzil-1,3,4- tiyadiazol-2-amin(11), 5-[3- fenoksi)propil]-N-(2'-feniletil)-1,3,4- tiyadiazol-2-amin(12) bileşikleri sentezlendi. Sentezlenen bu (1-12) bileşikler UV-Vis, H-NMR, C-NMR ve FT-IR temel spektroskopi yöntemleriyle karakterize edildi. Yeni sentezlenen bu bileşiklerin antimikrobiyal aktiviteleri disk difüzyon deneyi ile incelendi. Bazı bakteri tipleri açısından bileşikler tarandı. Bileşiklerin tamamı (1-12) Staphylococcus aureus'e karşı inhibisyon zonu sergiliyor iken, bileşiklerden sadece bir tanesi (9) Enterococcus durans'a karşı inibisyon zonu sergilimiştir. Bunun yanında bileşiklerin hiçbiri diğer bakterilere karşı inibisyon zonu sergilememiştir.

5-[3-phenoxy)propyl]-N-[3'-chlorophenyl]-1,3,4-thiadiazol-2-amine (1), 5-[3-phenoxy)propyl]-N--[4'-chlorophenyl]-1,3,4-thiadiazol-2-amine (2), 5-[3-phenoxy)propyl]-N-[2'-fluorophenyl]-1,3,4-thiadiazol-2-amine (3), 5-[3-phenoxy)propyl]-N-[3'-fluorophenyl]-1,3,4-thiadiazol-2-amine (4), 5-[3-phenoxy)propyl]-N-[4'-fluoro phenyl]-1,3,4-thiadiazol-2-amine (5), 5-[3-phenoxy)propyl]-N-[2'-methoxyphenyl]-1,3,4-thiadiazol-2-amine (6), 5-[3-phenoxy)propyl]-N-[3'-methoxyphenyl]-1,3,4-thiadiazol-2-amine (7), 5-[3-phenoxy)propyl]-N-[4'-methoxyphenyl]-1,3,4-thiadiazol-2-amine (8), 5-[3-phenoxy)propyl]-N-[4'-nitrophenyl]-1,3,4-thiadiazol-2-amine (9), 5-[3-phenoxy)propyl]-N-[2'-methoxycarbonylphenyl]-1,3,4-thiadiazol-2-amine (10), 5-[3-phenoxy)propyl]-N-benzyl-1,3,4-thiadiazol-2-amine (11), 5-[3-phenoxy)propyl]-N-(2'-phenylethyl)-1,3,4-thiadiazol-2-amine (12) were synthesized by the reaction of 4 phenoxy butiric acid and phenylthiosemicarbazide derivatives with phosphorous oxychloride. Antibacterial activity was studied for selected bacteria. Compounds 1-12 were synthesized and characterized with UV, FT-IR, 13C-NMR, 1H-NMR elemental methods. Compounds 1-12 were screened for some bacteria types. The compounds (1-12) showed inhibition zones on Staphylococcus aureus while compund (9) had an effect on Enterococcus durans. However, none of the compounds exhibited an inhibition zone against other bactericides.