Bazı yeni sinnamik asit türevi 1,3,4-tiyadiazol bileşiklerinin sentezi, karakterizasyonu ve antimikrobiyal aktivitelerinin belirlenmesi

Abstract

ÖZETYüksek Lisans TeziBu tez çalışmasında 3,4-(metilen dioksi) sinnamik asit ile N-fenil tiyosemikarbazit türevlerinin fosfor oksiklorür katalizörlüğündeki reaksiyonundan, 5-[2-(1,3-benzodioksol-5-il)etenil]-N-fenil-1,3,4-tiyadiazol-2-amin(1),5-[2-(1,3-benzodioksol-5-il)etenil]-N-[2'-klorofenil]-1,3,4-tiyadiazol-2-amin (2), 5-[2-(1,3-benzodioksol-5-il)etenil]-N-[4'-klorofenil]-1,3,4- tiyadiazol-2-amin (3),5-[2-(1,3-benzodioksol-5-il)etenil]-N-[2'-florofenil]-1,3,4- tiyadiazol-2-amin (4),5-[2-(1,3-benzodioksol-5-il)etenil]-N-[3'-florofenil]-1,3,4- tiyadiazol-2-amin (5),5-[2-(1,3-benzodioksol-5-il)etenil]-N-[4'-florofenil]-1,3,4- tiyadiazol-2-amin (6),5-[2-(1,3-benzodioksol-5-il)etenil]-N-[2'-metoksifenil]-1,3,4-tiyadiazol-2-amin (7),5-[2-(1,3-benzodioksol-5-il)etenil]-N-[3'- metoksifenil]-1,3,4-tiyadiazol-2-amin (8),5-[2-(1,3-benzodioksol-5-il)etenil]-N-[4'- metoksifenil]-1,3,4-tiyadiazol-2-amin(9), 5-[2-(1,3-benzodioksol-5-il)etenil]-N-[2',4'-diklorofenil]-1,3,4- tiyadiazol-2-amin (10),5-[2-(1,3- benzodioksol-5-il)etenil]-N-[4'-nitrofenil]-1,3,4- tiyadiazol-2-amin (11),5-[2-(1,3- benzodioksol-5-il)etenil]-N-[2'-etilfenil]-1,3,4- tiyadiazol-2-amin (12),5-[2-(1,3-benzodioksol-5-il)etenil]-N-[2'-metoksikarbonilfenil]-1,3,4-tiyadiazol-2-amin(13),5-[2-(1,3-benzodi ok sol -5-il) etenil]-N-benzil-1,3,4-tiyadiazol-2-amin (14),5-[2-(1,3-benzodioksol-5-il)etenil]-N-(2'-feniletil)-1,3,4-tiyadiazol-2-amin (15) bileşikleri sentezlendi.. Sentezlenen bileşikler UV, FT-IR, 13C-NMR, 1H-NMR elemental yöntemleri ile karakterize edildi. Bu bileşiklerin bazı bakteriler ve mantar üzerinde antimikrobiyal aktivitesi incelendi Bazı bileşiklerin test mikroorganizmalarına karşı orta düzeyde aktivite gösterdiği bulundu. 5, 7, 10, 13, 14 numaralı bileşikler Staphylococcus auries üzerinde inhibisyon zonu sergiliyor iken, bileşik 7 Enterococcus durans üzerinde inhibisyon zonu göstermiştir. Bileşik 8 E. coli üzerinde, bileşik 9 Enterobacter aerogenes üzerinde ve bileşik 13 Salmonella Kentucky üzerinde inhibisyon zonu göstermiştir Ancak bileşiklerin hiçbiri Candida albicans, Salmonella infants, Salmonella typhimurium, Salmonella enteritidis ve Bacillus subtilis üzerinde aktivite göstermemişlerdir.

5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-phenyl-1,3,4-thiadiazol-2-amine (1), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[2'-chlorophenyl]-1,3,4-thiadiazol-2-amine (2), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[4'-chlorophenyl]-1,3,4-thiadiazol-2-amine (3), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[2'-fluorophenyl]-1,3,4-thiadiazol-2-amine (4), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[3'-fluorophenyl]-1,3,4-thiadiazol-2-amine(5) ,5-[2-(1,3-benzodioxol-5-yl) ethenyl]-N-[4'-fluorophenyl]-1,3,4-thiadiazol-2-amine (6), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[2'-methoxyphenyl]-1,3,4-thiadiazol-2-amine (7), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[3'-methoxyphenyl]-1,3,4-thiadiazol -2-amine (8), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[4'-methoxyphenyl]-1,3,4-thiadiazol-2-amine (9), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[2',4'-dichlorophenyl]-1,3,4-thiadiazol-2-amine (10), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[4'-nitrophenyl]-1,3,4-thiadiazol-2-amine (11), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[2'-ethylphenyl]-1,3,4-thiadiazol-2-amine (12), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-[2'-methoxycarbonylphenyl]-1,3,4-thiadiazol-2-amine (13), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-benzyl-1,3,4-thiadiazol-2-amine (14), 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-N-(2'-phenylethyl)-1,3,4-thiadiazol-2-amine (15) were synthesized by the reaction of phenylthiosemicarbazide derivatives and cynnamic acid derivatives with phosphorous oxychloride. Antibacterial activity was studied for selected bacteria. Compounds 1-15 synthesized and characterized with UV, FT-IR, 13C-NMR, 1H-NMR elemental methods. Compounds 1-15 were screened for five bacteria types. The newly synthesized compounds were investigated for their antimicrobial activities with disk diffusion method. Some of compounds were found to have moderate activities against test microorganisms. The compounds (5,7,10,13,14) showed inhibition zones on Staphylococcus auries, while compund (7) showed inhibition zones on Enterococcus durans. Compund (8) showed inhibition zones on E.coli. Compound (9) showed inhibition zones on Enterobacter aerogenes. Compound (13) showed inhibition zones on Salmonella Kentucky. But all compounds had no activity against on Candida albicans, Salmonella infants, Salmonella typhimurium, Salmonella enteritidis and Bacillus subtilis.