Facile One-Pot Synthesis Methodology for Nitrogen-Containing Heterocyclic Derivatives of 3,5-Disubstituted 4,5-Dihydro-1H-Pyrazole, Their Biological Evaluation and Molecular Docking Studies
- 作者: Upadhyay S.1, Tripathi A.1, Paliwal S.2, Saraf S.1
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隶属关系:
- Faculty of Pharmacy, Babu Banarasi Das Northern India Institute of Technology
- Department of Pharmacy, Banasthali Vidyapith, Banasthali
- 期: 卷 51, 编号 7 (2017)
- 页面: 564-575
- 栏目: Article
- URL: https://journals.rcsi.science/0091-150X/article/view/244710
- DOI: https://doi.org/10.1007/s11094-017-1655-7
- ID: 244710
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详细
A series of 2-pyrazoline derivatives (PS-1 to PS-16) were synthesized by reacting different aromatic/heteroaromatic aldehydes and ketones, in a two-step reaction through Claisen – Schmidt condensation, followed by cyclization of the resulting chalcones with hydrazine hydrate in the presence of a base using conventional and microwave approaches. The synthesized derivatives were characterized by various physicochemical methods including IR, 1H-NMR, 13C-NMR, and mass spectroscopic data and elemental analysis. The antidepressant and anti-anxiety activities were evaluated using suitable animal models. Compounds PS-3, and PS-14 showed noticeable antidepressant activity, by reducing the duration of immobility in both tests, while compounds PS-9 and PS-12 were found to possess good anxiolytic activity (by increasing the number of arm entries and open arm exploratory time) at the tested doses (50 and 100 mg/kg b.w.) in comparison to standard drugs imipramine and diazepam, respectively. In order to elucidate binding interactions of the synthesized derivatives to the MAO-A target protein, molecular docking was employed which demonstrated the key interactions with amino acid residues Phe208, Asn181, and Tyr407 at the binding site. Further, the ADME properties of the synthesized derivatives were predicted and found to fall within the stated limits.
作者简介
Savita Upadhyay
Faculty of Pharmacy, Babu Banarasi Das Northern India Institute of Technology
Email: dirpharmniec@gmail.com
印度, Lucknow, U. P., 227105
Avinash Tripathi
Faculty of Pharmacy, Babu Banarasi Das Northern India Institute of Technology
Email: dirpharmniec@gmail.com
印度, Lucknow, U. P., 227105
Sarvesh Paliwal
Department of Pharmacy, Banasthali Vidyapith, Banasthali
Email: dirpharmniec@gmail.com
印度, Tonk, Rajasthan, 304022
Shailendra Saraf
Faculty of Pharmacy, Babu Banarasi Das Northern India Institute of Technology
编辑信件的主要联系方式.
Email: dirpharmniec@gmail.com
印度, Lucknow, U. P., 227105