Synthesis, In Vitro Anticholinesterase and Antimicrobial Evaluation of New 1,3,4-Thiadiazole-Piperazine Derivatives

Abstract

In this study, 8 new compounds having 2-((5-substituted-1,3,4-thiadazol-2-yl)amino)-2-oxoethyl-4- substituepiperazine-1-carbodithioate structures were synthesized, antimicrobial and anticholinesterase activities were evaluated. The structures of synthesized compounds were proved by 1H NMR, 13C NMR and mass spectra. The synthesized compounds were tested for antibacterial activity against eight bacteria strains and antifungal activity against four fungus strains. When the antibacterial activities of the compounds were examined, it was found that the compounds 3c, 3d, 3g and 3h were effective against E. faecalis (ATCC 29212) and E. faecalis (ATCC 51922) with MIC value of 25 µg/mL. It was determined that the carbon chain at the para position of piperazine increased the activity but where as the addition of benzyl group to the para position (3a, 3b, 3e, 3f) did not affect the activity. Furthermore, the acetylcholinesterase activity of the synthesized compounds was examined but none of the compounds showed AChE inhibitory activity as much as standard drug Donepezil.

Keywords

• 1
• 3
• 4-Thiadiazole
• Antimicrobial
• Anticholinesterase
• Piperazine

Yeni 1,3,4-Tiyadiazol-Piperazin Türevlerinin Sentezi, İn Vitro Antikolinesteraz ve Antimikrobiyal Değerlendirilmesi

Abstract

Bu çalışmada 2-((5-substitüe-1,3,4-tiyadiazl-2-il)amino)-2-oksoetil-4- substituepiperazin-1-karboditiyat yapısında 8 yeni bileşiğin sentezi yapılarak, antimikrobiyal ve antikolinesteraz aktiviteleri incelenmiştir. Sentezlenen bileşiklerin yapıları ¹H-NMR, ¹³ C-NMR ve kütle spektrumları kullanılarak kanıtlanmıştır. Aktivite sonuçları incelendiğinde, çoğu bileşiğin S. aureus (ATCC 25923), E. fecalis (ATCC 29212), E. fecalis (ATCC 51922), L. monocytogenes (ATCC 1911), K. pneumoniae (ATCC 700603), P. aeruginosa (ATCC 27853), E.coli (ATCC 35218), E. coli (ATCC 25923), C. albicans (ATCC 90028), C. glabrata (ATCC 90030), C. krusei (ATCC  6258), C. parapsilopsis (ATCC 22019) karşı standart bileşikler olan kloramfenikol ve ketakonazol kadar etkili olmadıkları görülmüştür. Bileşiklerin antibakteriyel aktiviteleri incelendiğinde 3c, 3d, 3g ve 3h kodlu bileşiklerin diğer bileşiklere göre daha yüksek aktiviteye sahip olduğu görülmüştür. Piperazinin para konumunda bulunan karbon zincirinin aktiviteyi arttırdığı (3c, 3d, 3g, 3h), ancak para konumuna benzil grubunun eklenmesinin (3a, 3b, 3e, 3f) aktiviteyi etkilemediği belirlenmiştir. Ayrıca, sentezlenen bileşiklerin asetilkolinesteraz aktivitesi incelenmiş ancak bileşiklerden hiçbiri standart ilaç Donepezil kadar AChE inhibe edici aktivite göstermemiştir.

Keywords

• Thiadiazole
• Antimicrobial
• Anticholinesterase
• Piperazine

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