Biological evaluation of some tetrazole derivatives as cholinesterase inhibitors

Year 2014, Volume: 4 Issue: 1, 1 - 4, 25.04.2014

Usama Abu Mohsen Leyla Yurttaş Ahmet Özdemir Gülhan Turan-zitouni Zafer Asim Kaplancikli

Abstract

Objectives: In this study, we aimed to synthesize fourteen different 2-[(1-methyl-1H-tetrazole-5-yl) thio]-1-(substituted phenyl)ethanone derivatives (1–14) and to investigate their anticholinesterase activities.

Method: 1-(Substituted phenyl)-2-[(1-methyl-1H-tetrazol-5-yl) thio]ethanone compounds were synthesized by reacting 1-methyl-1H-tetrazol-5-thiol with some phenacyl bromide derivatives. The structures of the obtained compounds were elucidated using IR, 1H-NMR, 13C-NMR and FAB+-MS spectral data and elemental analyses results. Each derivative was evaluated for its ability to inhibit acetylcholinesterase (AChE) using a modification of Ellman’s spectrophotometric method.

Results: The compound 2 and 3 were found as the most active compounds due to their inhibitory effect on AChE with inhibition percentages of 29.56 and 24.38%.

Conclusion: The compounds with electron donating substituents methyl and chloro at the third position of phenyl residue have exhibited the highest anticholinesterase activity.

Key words: Tetrazole, cholinesterase inhibitors

Keywords

Tetrazole, cholinesterase inhibitors

Bazı tetrazol türevlerinin kolinesteraz inhibitörü olarak biyolojik açıdan değerlendirilmesi

Abstract

Amaç: Bu çalışmada, ondört farklı 2-[(1-metil-1H-tetrazol-5-il)tiyo]-1-(sübstitüe fenil) etanon (1–14) türevinin sentezleri ve antikolinesteraz aktivitelerinin araştırılması amaçlandı. 

Yöntem: 1-(Sübstitüe fenil)-2-[(1-metil-1H-tetrazol-5-il) tiyo]etanon (1–14) türevi bileşikler, 1-metil-1H-tetrazol-5-tiyol ile bazı fenaçil bromür türevlerinin reaksiyonuyla sentezlenmiştir. Bileşiklerin kimyasal yapıları, IR, 1H-NMR, 13C-NMR ve FAB+-MS spektral verileri ve elementel analiz verileri ile aydınlatılmıştır. Tüm türevlerin asetilkolinesteraz enzimini (AChE) inhibisyon yetenekleri modifiye Ellman spektrofotometrik metodu kullanılarak değerlendirilmiştir.

Bulgular: Bileşik 2 ve 3 AChE üzerinde %29.56 ve %24.38 inhibisyon oranları ile en aktif bileşikler olarak bulunmuştur.

Sonuç: Bileşiklerden fenil artığı üzerinde 3-konumunda elektron verici metil ve kloro sübstitüentleri içerenler en yüksek antikolinesteraz aktivite göstermişlerdir.

Anahtar Kelimeler : Tetrazol, kolinesteraz inhibitörleri

Keywords

Tetrazol, kolinesteraz inhibitörleri

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