Synthesis and biological evaluation of 1,2,4-triazolidine-3-thiones as potent acetylcholinesterase inhibitors: in vitro
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ORIGINAL ARTICLE
Synthesis and biological evaluation of 1,2,4‑triazolidine‑3‑thiones as potent acetylcholinesterase inhibitors: in vitro and in silico analysis through kinetics, chemoinformatics and computational approaches Prasad G. Mahajan1 · Nilam C. Dige2 · Balasaheb D. Vanjare1 · Hussain Raza2 · Mubashir Hassan3 · Sung‑Yum Seo2 · Chong‑ Hyeak Kim4 · Ki Hwan Lee1 Received: 29 April 2019 / Accepted: 25 July 2019 © Springer Nature Switzerland AG 2019
Abstract We have designed and synthesized a novel acidic ionic liquid and explored its catalytic efficiency for the synthesis of 1,2,4-triazolidine-3-thione derivatives. A simple reaction between aldehydes and thiosemicarbazide for short time in 60:40 v/v water/ethanol at room temperature offers target 1,2,4-triazolidine-3-thione derivatives. The formation of target compounds is confirmed by NMR, IR and ESI–MS analysis. Pleasingly, synthesized compounds show noteworthy acetylcholinesterase (AChE) inhibitory activity with much lower I C50 values 0.0269 ± 0.0021–1.1725 ± 0.0112 μM than standard Neostigmine methylsulphate. In addition, synthesized 1,2,4-triazolidine-3-thiones exhibits significant free radical scavenging activity as compared to standard vitamin C. The studies on validation of Lipinski’s rule through chemoinformatics properties and molecular docking analysis are in support of in vitro analysis. Therefore, overall present study illustrates synthesis of some new 1,2,4-triazolidines-3-thiones which can serve as a template for drug designing such as AChE inhibitors. Graphic abstract Herein, we proposed ionic liquid-catalyzed ease of synthetic approach for medicinally important 1,2,4-triazolidine-3-thiones and their bio-evaluations.
Keywords Ionic liquid · 1,2,4-triazolidine-3-thiones · Acetylcholinesterase inhibition · Lipinski rule · Molecular docking
Introduction Prasad G. Mahajan and Nilam C. Dige have contributed equally for this research work. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11030-019-09983-y) contains supplementary material, which is available to authorized users. Extended author information available on the last page of the article
Being eco-friendly catalyst, versatile reaction medium and safe solvent for the synthetic methodology enhance the utility of ionic liquids (ILs) in organic chemistry. ILs shows unique properties such as low vapour pressure, high chemical, thermal as well as electrochemical stability, significant viscosity and low flammability. Such a characteristics of ILs,
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increases their significance in industrial area for the development of science and engineering field [1–4]. The distinct structure, unique physicochemical properties and ionic interactions of ILs were widely explored in organic synthesis [5], catalysis [6], extraction [7] and C O2/SO2 capture [8, 9]. In addition, non-volatile and non-corrosive nature, air stability, simple recovery and recycling process have gained significant research of interest in sulphate functional
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