Microwave-Assisted Synthesis, In Vivo Anti-Inflammatory and In Vitro Anti-Oxidant Activities, and Molecular Docking Study of New Substituted Schiff Base Derivatives
- Authors: Hanif M.1, Hassan M.2, Rafiq M.2,3, Abbas Q.4, Ishaq A.5, Shahzadi S.6,7, Seo S.1, Saleem M.8
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Affiliations:
- College of Natural Sciences, Department of Biology, Kongju National University
- Department of Chemistry, Government College University
- Department of Biochemistry and Biotechnology (Baghdad-ul-Jadeed Campus), The Islamia University of Bahawalpur
- Department of Physiology, University of Sindh
- Department of Chemistry, University of Sargodha (Sub-Campus Mianwali)
- Department of Bioinformatics, Virtual University (Davis Road Campus)
- Institute of Molecular Science and Bioinformatics
- Department of Chemistry, University of Sargodha, sub-campus Bhakkar
- Issue: Vol 52, No 5 (2018)
- Pages: 424-437
- Section: Article
- URL: https://journals.rcsi.science/0091-150X/article/view/245231
- DOI: https://doi.org/10.1007/s11094-018-1835-0
- ID: 245231
Cite item
Abstract
In view of considerable interest in the design and synthesis of new heterocyclic compounds with promising biological activities for medical and biological applications, a series of eight imine derivatives have been synthesized through microwave-assisted Schiff base formation by reacting 2-(4-methoxyphenyl)acetohydrazide (3) and 4-amino-3-(4-methoxybenzyl)-1H-1,2,4-triazole-5(4H)-thione (6) with various substituted aldehydes. Structures of the newly synthesized compounds were characterized by FT-IR, 1H NMR and 13C NMR spectral analysis. All the synthesized derivatives were screened for their in vivo anti-inflammatory and in vitro anti-oxidant activities using carrageenan induced rat paw edema test and DPPH free radical scavenging assay, respectively. In addition, molecular docking experiment was also performed to check the actual binding affinity of ligand against target protein. Compounds 4a, 4c, 7a, and 7c screened as potent anti-inflammatory drugs significantly lowered the volume of rat paw edema (P < 0.05). In case of anti-oxidant assay, compound 7a with ferrocenyl group as substituent R and 3,4-disubstitued 1,2,4-triazole as side coupled group exhibited IC50 value of 7.2 ± 2.7 μg/mL comparable with that of the reference ascorbic acid (2.61 ± 0.29 μg/mL) and was the most active compound among the series. However, no prominent results were obtained in case of aralkanoic acid hydrazide substituted Schiff base derivatives 4a – 4d. It is believed that the synthesized Schiff base derivatives can be used for the development of potent anti-inflammatory and anti-oxidant drugs with considerable advantages of convenient synthetic strategy possessing high product yield, short reaction time, and convenient handling. The molecular docking results were found in good correlation with experimental IC50 values.
About the authors
Muhammad Hanif
College of Natural Sciences, Department of Biology, Kongju National University
Email: saleemqau@gmail.com
Korea, Republic of, Gongju, Chungcheongnam, 32588
Mubashir Hassan
Department of Chemistry, Government College University
Email: saleemqau@gmail.com
Pakistan, Faisalabad (Sub-Campus Layyah)
Muhammad Rafiq
Department of Chemistry, Government College University; Department of Biochemistry and Biotechnology (Baghdad-ul-Jadeed Campus), The Islamia University of Bahawalpur
Email: saleemqau@gmail.com
Pakistan, Faisalabad (Sub-Campus Layyah); Bahawalpur, 63100
Qamar Abbas
Department of Physiology, University of Sindh
Email: saleemqau@gmail.com
Pakistan, Jamshoro, 76080
Ansa Ishaq
Department of Chemistry, University of Sargodha (Sub-Campus Mianwali)
Email: saleemqau@gmail.com
Pakistan, Mianwali
Saba Shahzadi
Department of Bioinformatics, Virtual University (Davis Road Campus); Institute of Molecular Science and Bioinformatics
Email: saleemqau@gmail.com
Pakistan, Lahore; 28 Nisbet Road, Opt. Dyal Singh Trust Library, Lahore, 54000
Sung-Yum Seo
College of Natural Sciences, Department of Biology, Kongju National University
Email: saleemqau@gmail.com
Korea, Republic of, Gongju, Chungcheongnam, 32588
Muhammad Saleem
Department of Chemistry, University of Sargodha, sub-campus Bhakkar
Author for correspondence.
Email: saleemqau@gmail.com
Pakistan, Bhakkar