Environmentally benign synthesis of substituted pyrazoles as potent antioxidant agents, characterization and docking stu
- PDF / 2,635,365 Bytes
- 15 Pages / 595.276 x 790.866 pts Page_size
- 65 Downloads / 230 Views
ORIGINAL PAPER
Environmentally benign synthesis of substituted pyrazoles as potent antioxidant agents, characterization and docking studies Channa Basappa Vagish1 · Achutha Dileep Kumar1 · Karthik Kumara2,5 · Hamse Kameshwar Vivek3 · Nagamallu Renuka4 · Neratur Krishnappagowda Lokanath2 · Kariyappa Ajay Kumar1 Received: 27 April 2020 / Accepted: 14 August 2020 © Iranian Chemical Society 2020
Abstract Oxidative stress is an important cause of neurogenerative diseases; treatment with a reliable antioxidant with no side effects is a potential tool to overcome with such diseases. The aim of this study is to explore new and effective antioxidants and their mechanism; in this context, the manuscript demonstrates the greener approach for the synthesis of series of novel thiophenepyrazole hybrids, 5(a–m) through [3 + 2] annulation of chalcones, 3(a–g) and phenylhydrazine hydrochloride, 4(a–b) in citrus extract medium in the presence of tetrabutylammonium bromide. The structures were confirmed by spectroscopic and crystallographic studies and further screened in vitro for their free radical scavenging activities. Preliminary assessment results show that, among the synthesized series, compounds 5c, 5d, 5f, 5i, 5j, 5l, and 5m have potent antioxidant activities. Docking studies reveal that the ligands 5e, 5f, 5m, and 5q bind to superoxide dismutase at the Cu–Zn domain and thereby increase its activity and reduce reactive oxygen species; therefore, these ligands might be better antioxidant molecules which could down and regulate the oxidation stress within the body. Keywords Annulation · Chalcones · Condensation · Hydroxyl · Radical · Scavenging Abbreviations TBAB Tetrabutylammonium bromide DNA Deoxyribonucleic acid ROS Reactive oxygen species PC12 Pheochromocytoma 12 cell lines Nrf2 Nuclear factor erythroid 2-related factor 2 TNF-α Tumour necrosis factor alpha Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13738-020-02042-6) contains supplementary material, which is available to authorized users. * Kariyappa Ajay Kumar [email protected]‑mysore.ac.in 1
IL-6 Interleukin 6 AAPH-2,2’ Azobis(2-amidinopropane) dihydrochloride DPPH 2,2-Diphenyl-1-picrylhydrazyl TLC Thin-layer chromatography NMR Nuclear magnetic resonance ESI Electrospray APCI Atmospheric pressure chemical ionization UPLC Ultimate performance liquid chromatography CCD Charge couple device CCDC Cambridge Crystallographic Data Centre OPLS Optimized potentials for liquid simulations Cu–Zn SOD Cu–Zn superoxide dismutase PDB Protein Data Bank
Department of Chemistry, Yuvaraja College, University of Mysore, Mysuru, India
2
Department of Studies in Physics, University of Mysore, Manasagangotri, Mysuru, India
Introduction
3
Research and Innovation Center, BGSIT Campus, Adichunchanagiri University, B.G. Nagara, Mandya, India
4
Department of Chemistry, GSSS Institute of Engineering and Technology for Women, Mysuru, India
5
Present Address: Department of Physics, School of Sciences, Jain
Data Loading...
