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

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

Three new tetradentate NNNS Schiff bases (<b>L1</b>–<b>L3</b>) 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 ald...

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Main Authors: Ismail Warad, Oraib Ali, Anas Al Ali, Nidal Amin Jaradat, Fatima Hussein, Lubna Abdallah, Nabil Al-Zaqri, Ali Alsalme, Fahad A. Alharthi
Format: Article
Language:English
Published: MDPI AG 2020-05-01
Series:Molecules
Subjects:
Schiff base
antimicrobial
DFT
pancreatic lipase inhibitors
Online Access:https://www.mdpi.com/1420-3049/25/9/2253
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spelling doaj-af15f1d161584ababfc68cd034a3d6412020-11-25T02:04:34ZengMDPI AGMolecules1420-30492020-05-01252253225310.3390/molecules25092253Synthesis 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 InvestigationsIsmail Warad0Oraib Ali1Anas Al Ali2Nidal Amin Jaradat3Fatima Hussein4Lubna Abdallah5Nabil Al-Zaqri6Ali Alsalme7Fahad A. Alharthi8Department of Chemistry and Earth Sciences, Qatar University, P.O. Box 2713, Doha, QatarDepartment of Chemistry, Science College, An-Najah National University, P.O. Box 7, Nablus, PalestineDepartment of Chemistry, Science College, An-Najah National University, P.O. Box 7, Nablus, PalestineDepartment of Pharmacy, Faculty of Medicine and Health Sciences, An-Najah National University, P.O. Box 7, Nablus, PalestineDepartment of Pharmacy, Faculty of Medicine and Health Sciences, An-Najah National University, P.O. Box 7, Nablus, PalestineDepartment of Biology and Biotechnology Science College, An-Najah National University, P.O. Box 7, Nablus, PalestineDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaThree new tetradentate NNNS Schiff bases (<b>L1</b>–<b>L3</b>) 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 <sup>1</sup>H and <sup>13</sup>C 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 <b>L2</b>. 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 IC<sub>50</sub> 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.https://www.mdpi.com/1420-3049/25/9/2253Schiff baseantimicrobialDFTpancreatic lipase inhibitors
collection DOAJ
language English
format Article
sources DOAJ
author Ismail Warad
Oraib Ali
Anas Al Ali
Nidal Amin Jaradat
Fatima Hussein
Lubna Abdallah
Nabil Al-Zaqri
Ali Alsalme
Fahad A. Alharthi
spellingShingle Ismail Warad
Oraib Ali
Anas Al Ali
Nidal Amin Jaradat
Fatima Hussein
Lubna Abdallah
Nabil Al-Zaqri
Ali Alsalme
Fahad A. Alharthi
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
Molecules
Schiff base
antimicrobial
DFT
pancreatic lipase inhibitors
author_facet Ismail Warad
Oraib Ali
Anas Al Ali
Nidal Amin Jaradat
Fatima Hussein
Lubna Abdallah
Nabil Al-Zaqri
Ali Alsalme
Fahad A. Alharthi
author_sort Ismail Warad
title 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
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort 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
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2020-05-01
description Three new tetradentate NNNS Schiff bases (<b>L1</b>–<b>L3</b>) 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 <sup>1</sup>H and <sup>13</sup>C 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 <b>L2</b>. 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 IC<sub>50</sub> 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.
topic Schiff base
antimicrobial
DFT
pancreatic lipase inhibitors
url https://www.mdpi.com/1420-3049/25/9/2253
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