Synthesis of Indole-3-Carboxyaldehyde Thiosemicarbazone Derivatives and Investigation of Antioxidant and Anticholinesterase Properties

Year 2019, Volume: 19 Issue: 2, 317 - 327, 17.09.2019

Murat Bingül

Abstract

The
synthesis of four indole-3-carboxyaldehyde thiosemicarbazone compounds (3a-d) was achieved via the Schiff base
reaction of the indole-3-carboxyaldehyde and thiosemicarbazides in high yields.
The structures of thiosemicarbazones 3a and
3b were supported by ¹HNMR
spectroscopy and confirmed with the literature data. To the best of our
knowledge, our study is the first report for the synthesis of compound 3c and literature search revealed that
compound 3d was also not fully
characterised. The structures of compound 3c
and 3d were fully characterised by
the FT-IR, High Resolution Mass Spectrometry (HRMS), ¹H and ¹³CNMR
spectroscopy in this work for the first time. Moreover, antioxidant properties
of synthesised compounds 3a-d were determined by employing three
different assays, namely DPPH radical scavenging, ABTS Cation Radical
Decolarization and CUPRAC Cupric Reducing Antioxidant Capacity as well as the
anticholinesterase properties of designated compounds were investigated by the
Acetylcholinesterase (ACh) and Butyrylcholinesterase (BCh) enzyme inhibition
assays. The compound 3a, 3b and 3d were
determined very potent against the ABTS antioxidant assay and compound 3c was found to be a valuable target molecule for the kinetic
measurements to identify mechanism of action in the area of anticholinesterase
activity assay.

Keywords

Indole; Thiosemicarbazone; Antioxidant; Anticholinesterase

İndol-3-Karboksialdehit Tiyosemikarbazon Türevlerinin Sentezi Antioksidan ve Antikolinesteraz özelliklerinin araştırılması

Abstract

Dört
indol-3-karboksialdehit tiyosemikarbazon bileşiği indol-3-karboksialdehit ve
tiyosemikarbazit bileşiklerinden Schiff bazı reaksiyonu kullanılarak yüksek
verimlerde sentezlenmiştir. 3a ve 3b tiyosemikarbazon yapıları ¹HNMR
spektroskopisiyle desteklenerek literatür verileriyle uyumlu olduğu
kanıtlanmıştır. Bildiğimiz kadarıyla, çalışmamız 3c bileşiğinin sentezi ve 3d
bileşiğinin tüm karakterizasyonlarının yapılması açısından ilk bilimsel
çalışmadır. 3c ve 3d bileşiklerinin yapıları, FT-IR,
yüksek çözünürlüklü kütle spektroskopisi,
¹H ve ¹³CNMR spektroskopileri ile ilk olarak bu çalışmada
aydınlatılmıştır. Dahası, sentezlenen 3a-d
bileşiklerinin antioksidan özellikleri üç farklı DPPH serbest radikal süpürme,
ABTS katyonik radikal süpürme, CUPRAC kuprik iyonunu indirgeme kapasitesi
yöntemlerinin uygulanmasıyla belirlenmiştir. Bununla beraber, belirtilen
bileşiklerin antikolinesteraz özellikleri, Asetilkolinesteraz (ACh) ve
Bütirilkolinesteraz (BCh) enzim inhibisyonu deneyleriyle araştırılmıştır. 3a, 3b ve 3d bileşiklerinin
ABTS antioksidan metodu için çok etkili olduğu belirlenmiş ve 3c bileşiğinin antikolinesteraz
aktivite alanında kinetik ölçümlerinin yapılarak etki mekanizmasının
aydınlatılması konusunda değerli bir hedef molekül olduğu anlaşılmıştır. 

Keywords

İndole; Tiyosemikarbazon; Antioksidan; Antikolinesteraz

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