Synthesis and Spectral Identification of Three Schiff Bases with a 2-(Piperazin-1-yl)- N -(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

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

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Synthesis and Spectral Identification of Three Schiff Bases with a 2-(Piperazin-1-yl)- N -(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 and Fahad A Alharthi

Molecules (Basel, Switzerland), Vol.25(9), p.2253

11/05/2020

DOI: https://doi.org/10.3390/molecules25092253

PMCID: 7248877

PMID: 32403218

Abstract

Anti-Bacterial Agents - pharmacology

Antioxidants - pharmacology

Inhibitory Concentration 50

Klebsiella pneumoniae - drug effects

Ligands

Lipase - antagonists & inhibitors

Magnetic Resonance Spectroscopy

Mass Spectrometry

Molecular Docking Simulation

Pancreas - enzymology

Piperazine - chemistry

Pseudomonas aeruginosa - drug effects

Schiff Bases - chemical synthesis

Schiff Bases - chemistry

Schiff Bases - pharmacology

Spectrophotometry, Ultraviolet

Spectroscopy, Fourier Transform Infrared

Staphylococcus aureus - drug effects

Static Electricity

Temperature

Thiophenes - chemistry

X-Ray Diffraction

Three new tetradentate NNNS Schiff bases ( - ) 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 H and 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 . 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 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.

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Title: Synthesis and Spectral Identification of Three Schiff Bases with a 2-(Piperazin-1-yl)- N -(thiophen-2-yl methylene)ethanamine Moiety Acting as Novel Pancreatic Lipase Inhibitors: Thermal, DFT, Antioxidant, Antibacterial, and Molecular Docking Investigations
Creators - without role: Ismail Warad - Qatar University
Oraib Ali - An-Najah National University
Anas Al Ali - An-Najah National University
Nidal Amin Jaradat - An-Najah National University
Fatima Hussein - An-Najah National University
Lubna Abdallah - An-Najah National University
Nabil Al-Zaqri - King Saud University
Ali Alsalme - King Saud University
Fahad A Alharthi - King Saud University
Publication Details: Molecules (Basel, Switzerland), Vol.25(9), p.2253
Identifiers: 9950452208331
Academic Unit: King Saud University
Language: English
Resource Type: Journal article