Synthesis and Spectral Identification of Three Schiff Bases with a 2-(Piperazin-1-yl)-<i>N</i>-(thiophen-2-yl methylene)ethanamine Moiety Acting as Novel Pancreatic Lipase Inhibitors: Thermal, DFT, Antioxidant, Antibacterial, and Molecular Docking Investigations

Ismail Warad; Oraib Ali; Anas Al Ali; Nidal Amin Jaradat; Fatima Hussein; Lubna Abdallah; Nabil Al-Zaqri; Ali Alsalme; Fahad A. Alharthi

doi:10.3390/molecules25092253

Molecules (May 2020)

Synthesis and Spectral Identification of Three Schiff Bases with a 2-(Piperazin-1-yl)-<i>N</i>-(thiophen-2-yl methylene)ethanamine Moiety Acting as Novel Pancreatic Lipase Inhibitors: Thermal, DFT, Antioxidant, Antibacterial, and Molecular Docking Investigations

Ismail Warad,
Oraib Ali,
Anas Al Ali,
Nidal Amin Jaradat,
Fatima Hussein,
Lubna Abdallah,
Nabil Al-Zaqri,
Ali Alsalme,
Fahad A. Alharthi

Affiliations

Ismail Warad: Department of Chemistry and Earth Sciences, Qatar University, P.O. Box 2713, Doha, Qatar
Oraib Ali: Department of Chemistry, Science College, An-Najah National University, P.O. Box 7, Nablus, Palestine
Anas Al Ali: Department of Chemistry, Science College, An-Najah National University, P.O. Box 7, Nablus, Palestine
Nidal Amin Jaradat: Department of Pharmacy, Faculty of Medicine and Health Sciences, An-Najah National University, P.O. Box 7, Nablus, Palestine
Fatima Hussein: Department of Pharmacy, Faculty of Medicine and Health Sciences, An-Najah National University, P.O. Box 7, Nablus, Palestine
Lubna Abdallah: Department of Biology and Biotechnology Science College, An-Najah National University, P.O. Box 7, Nablus, Palestine
Nabil Al-Zaqri: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Ali Alsalme: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Fahad A. Alharthi: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia

DOI: https://doi.org/10.3390/molecules25092253
Journal volume & issue: Vol. 25, no. 9
p. 2253

Abstract

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Three new tetradentate NNNS Schiff bases (L1–L3) derived from 2-(piperidin-4-yl)ethanamine were prepared in high yields. UV–Visible and FTIR spectroscopy were used to monitor the dehydration reaction between 2-(piperidin-4-yl)ethanamine and the corresponding aldehydes. Structures of the derived Schiff bases were deduced by 1H and 13C NMR, FTIR, UV–Vis, MS, EA, EDS, and TG-derived physical measurements. DFT/B3LYP theoretical calculations for optimization, TD-DFT, frequency, Molecular Electrostatic Potential (MEP), and highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) / were performed for L2. The in vitro antimicrobial activities of the three Schiff bases were evaluated against several types of bacteria by disk diffusion test using Gentamicin as the standard antibiotic. Schiff bases revealed good antioxidant activity by the DPPH method, and the IC50 values were compared to the Trolox standard. Pancreatic porcine lipase inhibition assay of the synthesized compounds revealed promising activity as compared to the Orlistat reference.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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