Tags

Type your tag names separated by a space and hit enter

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.
Mol Divers 2019MD

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 IC50 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. Herein, we proposed ionic liquid-catalyzed ease of synthetic approach for medicinally important 1,2,4-triazolidine-3-thiones and their bio-evaluations.

Authors+Show Affiliations

Department of Chemistry, Kongju National University, Gongju, Chungnam, 32588, Republic of Korea.Department of Biological Sciences, Kongju National University, Gongju, Chungnam, 32588, Republic of Korea.Department of Chemistry, Kongju National University, Gongju, Chungnam, 32588, Republic of Korea.Department of Biological Sciences, Kongju National University, Gongju, Chungnam, 32588, Republic of Korea.Institute of Molecular Biology and Biotechnology, The University of Lahore, Defence Road, Lahore, 54590, Pakistan.Department of Biological Sciences, Kongju National University, Gongju, Chungnam, 32588, Republic of Korea. dnalove@kongju.ac.kr.Center for Chemical Analysis, Korea Research Institute of Chemical Technology, Yuseong, Daejeon, 34114, Republic of Korea.Department of Chemistry, Kongju National University, Gongju, Chungnam, 32588, Republic of Korea. khlee@kongju.ac.kr.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31396774

Citation

Mahajan, Prasad G., et al. "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." Molecular Diversity, 2019.
Mahajan PG, Dige NC, Vanjare BD, et al. 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. Mol Divers. 2019.
Mahajan, P. G., Dige, N. C., Vanjare, B. D., Raza, H., Hassan, M., Seo, S. Y., ... Lee, K. H. (2019). 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. Molecular Diversity, doi:10.1007/s11030-019-09983-y.
Mahajan PG, et al. 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. Mol Divers. 2019 Aug 8; PubMed PMID: 31396774.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 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. AU - Mahajan,Prasad G, AU - Dige,Nilam C, AU - Vanjare,Balasaheb D, AU - Raza,Hussain, AU - Hassan,Mubashir, AU - Seo,Sung-Yum, AU - Kim,Chong- Hyeak, AU - Lee,Ki Hwan, Y1 - 2019/08/08/ PY - 2019/04/29/received PY - 2019/07/25/accepted PY - 2019/8/10/entrez KW - 1,2,4-triazolidine-3-thiones KW - Acetylcholinesterase inhibition KW - Ionic liquid KW - Lipinski rule KW - Molecular docking JF - Molecular diversity JO - Mol. Divers. N2 - 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 IC50 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. Herein, we proposed ionic liquid-catalyzed ease of synthetic approach for medicinally important 1,2,4-triazolidine-3-thiones and their bio-evaluations. SN - 1573-501X UR - https://www.unboundmedicine.com/medline/citation/31396774/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 L2 - https://doi.org/10.1007/s11030-019-09983-y DB - PRIME DP - Unbound Medicine ER -